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(23E)-hydroxysqualene
rac-(2R)-2-((3aS,5aR,5bR,7aS,11aS,11bR)-5a,5b,8,8,11a,13b-hexamethylicosahydro-1H-cyclopenta[a]chrysen-3-yl)propanal + rac-(2R)-2-((3aR,5aS,5bS,7aR,11aR,11bS)-5a,5b,8,8,11a,13b-hexamethylicosahydro-1H-cyclopenta[a]chrysen-3-yl)propanal + rac-2-((3aR,5aS,5bS,7aR,11aR,11bS)-5a,5b,8,8,11a,13b-hexamethylicosahydro-1H-cyclopenta[a]chrysen-3-yl)prop-2-en-1-ol
-
-
-
-
?
(23E)-methylsqualene
rac-(5R,9S,10R,13R,14R,17S)-4,4,10,13,14-pentamethyl-17-((E)-6-methyloct-5-en-2-yl)-2,3,4,5,6,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene + rac-(5R,8S,9S,10R,13S,14S)-4,4,8,10,14-pentamethyl-17-((E)-6-methylocta-1,5-dien-2-yl)hexadecahydro-1H-cyclopenta[a]phenanthrene + rac-(3aR,5aS,5bS,7aR,11aR,11bS,13aS)-3-(but-1-en-2-yl)-5a,5b,8,8,11a,13b-hexamethylicosahydro-1H-cyclopenta[a]chrysene + rac-2-((3aR,5aS,5bS,7aR,11aR,11bS,13aS)-5a,5b,8,8,11a,13b-hexamethylicosahydro-1H-cyclopenta[a]chrysen-3-yl)butan-2-ol
-
-
-
-
?
(23Z)-hydroxysqualene
rac-(2R)-2-((3aS,5aR,5bR,7aS,11aS,11bR)-5a,5b,8,8,11a,13b-hexamethylicosahydro-1H-cyclopenta[a]chrysen-3-yl)propanal + rac-(2R)-2-((3aR,5aS,5bS,7aR,11aR,11bS)-5a,5b,8,8,11a,13b-hexamethylicosahydro-1H-cyclopenta[a]chrysen-3-yl)propanal + rac-2-((3aR,5aS,5bS,7aR,11aR,11bS)-5a,5b,8,8,11a,13b-hexamethylicosahydro-1H-cyclopenta[a]chrysen-3-yl)prop-2-en-1-ol + ((9beta,10alpha,13xi,20xi)-20,26-epoxydammar-24-ene)
-
-
-
-
?
(23Z)-methylsqualene
(23Z)-methylsqualene + rac-(3aR,5aS,5bS,7aR,11aR,11bS,13aS)-3-(but-1-en-2-yl)-5a,5b,8,8,11a,13b-hexamethylicosahydro-1H-cyclopenta[a]chrysene + rac-(3aR,5aS,5bS,7aR,11aR,11bS)-3-((E)-but-2-en-2-yl)-5a,5b,8,8,11a,13b-hexamethylicosahydro-1H-cyclopenta[a]chrysene
-
-
-
-
?
(2E)-methylsqualene
rac-(3aR,5aS,5bS,7aR,11aR,11bS,13aS)-8-ethyl-5a,5b,8,11a,13b-pentamethyl-3-(prop-1-en-2-yl)icosahydro-1H-cyclopenta[a]chrysene
-
-
-
-
?
(2E,6E)-farnesol + geraniol
drimane-8,11-diol + [(1R,2S)-2-[[(2E)-3,7-dimethylocta-2,6-dien-1-yl]oxy]-2,6,6-trimethylcyclohexyl]methanol + 8-O-geranyl-drimane-8,11-diol + drimenol + albicanol
drimane-8,11-diol is the major product of the wild-type enzyme
-
-
?
(2E,6E)-farnesol + H2O
8-O-((2E,6E)-farnesyl)-drimane-8,11-diol + drimane-8,11-diol + drimenol + albicanol
drimane-8,11-diol is the major product of the wild-type enzyme
-
-
?
(2E,6E)-farnesol + H2O
[(1S,4aS,8aS)-5,5,8a-trimethyl-2-methylidenedecahydronaphthalen-1-yl]methanol + [(1S,4aS,8aS)-2,5,5,8a-tetramethyl-1,4,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]methanol + (1S,2R,4aS,8aS)-1-(hydroxymethyl)-2,5,5,8a-tetramethyldecahydronaphthalen-2-ol + (1S,2R,4aS,8aS)-1-(hydroxymethyl)-2-O-((2E,6E)-farnesyl)-2,5,5,8a-tetramethyldecahydronaphthalen-2-ol
-
-
-
?
(2E,6E)-farnesol + n-butanol
drimane-8,11-diol + drimenol + albicanol + 8-O-((2E,6E)-farnesyl)-drimane-8,11-diol + drimane-8,11-diol + farnesyl pentyl ether
drimane-8,11-diol is the major product of the wild-type enzyme
-
-
?
(3R)-2,3-oxidosqualene + H2O
3alpha-hydroxyhopene + 3alpha-hydroxyhopanol
-
-
-
?
(3S)-2,3-oxidosqualene
lanosterol
-
-
-
-
?
(3S)-2,3-oxidosqualene + H2O
3beta-hydroxyhopene + 3beta-hydroxyhopanol
-
-
-
?
(6E)-3,7,11-trimethyldodeca-1,6,10-trien-3-ol
(-)-caparrapioxide + (-)-8-epi-caparrapioxide
-
-
-
-
?
(6E,10E)-2,6,10-trimethyldodeca-2,6,10-triene
(4aR,5S,8aS)-1,1,4a,5,6-pentamethyl-1,2,3,4,4a,5,8,8a-octahydronaphthalene + (4aR,5S,8aS)-1,1,4a,5-tetramethyl-6-methylidenedecahydronaphthalene + (1R,2R,4aS,8aS)-1,2,5,5,8a-pentamethyldecahydronaphthalen-2-ol + (1R,2S,4aS,8aS)-1,2,5,5,8a-pentamethyldecahydronaphthalen-2-ol + (4aS,8aS)-4,4,7,8,8a-pentamethyl-1,2,3,4,4a,5,6,8a-octahydronaphthalene + (3S,4aS,8aS)-3,4,4,8,8a-pentamethyl-1,2,3,4,4a,5,6,8a-octahydronaphthalene
-
via bicyclic C8-cation
-
-
?
(E,E)-homofarnesol
(-)-ambrox + (3aS,5aS,9aS,9bS)-3a,6,6,9a-tetramethyldodeca-hydronaphtho[2,1-b]furan
-
-
-
?
(E,E,E,E)-2,6,10,14,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene
8-(4,8-Dimethyl-nona-3,7-dienyl)-1,1,4a,8a-tetramethyl-7-methylene-tetradecahydro-phenanthrene
-
-
low conversion, NMR spectroscopic analysis
-
?
(E,E,E,E)-2,6,10,15,18,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene
1,1,4a,10a,10b-Pentamethyl-8-methylene-7-(4-methyl-pent-3-enyl)-octadecahydro-chrysene
-
-
one of the three major products, NMR spectroscopic analysis
-
?
(E,E,E,E)-2,6,10,15,18,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene
1,1,4a,6a,8,10a-Hexamethyl-7-(4-methyl-pent-3-enyl)-1,2,3,4,4a,4b,5,6,6a,7,8,9,10,10a,12,12a-hexadecahydro-chrysene
-
-
one of the three major products, NMR spectroscopic analysis
-
?
(E,E,E,E)-2,6,10,15,18,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene
1,1,4a,8,10a,10b-Hexamethyl-7-(4-methyl-pent-3-enyl)-1,2,3,4,4a,4b,5,6,8,9,10,10a,10b,11,12,12a-hexadecahydro-chrysene
-
-
one of the three major products, NMR spectroscopic analysis
-
?
(E,E,E,E)-2,6,10,15,18,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene
2,4a,4b,7,7,10a-Hexamethyl-1-(4-methyl-pent-3-enyl)-octadecahydro-chrysen-2-ol
-
-
minor product, NMR spectroscopic analysis
-
?
(E,E,E,E)-2,6,10,15,18,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene
2-(3a,5a,5b,8,8,11a-Hexamethyl-icosahydro-cyclopenta[a]chrysen-3-yl)-propan-2-ol
-
-
minor product, NMR spectroscopic analysis
-
?
(E,E,E,E)-2,6,10,15,18,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene
alpha-3-Isopropenyl-3a,5a,5b,8,8,11a-hexamethyl-icosahydro-cyclopenta[a]chrysene
-
-
minor product, NMR spectroscopic analysis
-
?
(E,E,E,E)-2,6,10,15,18,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene
beta-3-Isopropenyl-3a,5a,5b,8,8,11a-hexamethyl-icosahydro-cyclopenta[a]chrysene
-
-
minor product, NMR spectroscopic analysis
-
?
(E,E,E,E)-2,6,10,15,23-pentamethyltetracosa-2,6,10,14,18,22-hexaene
2-(5a,5b,8,8,11a-Pentamethyl-icosahydro-cyclopenta[a]chrysen-3-yl)-propan-2-ol
-
-
one of the three major products, yield 19.8%, NMR spectroscopic analysis
-
?
(E,E,E,E)-2,6,10,15,23-pentamethyltetracosa-2,6,10,14,18,22-hexaene
3-Isopropenyl-5a,5b,8,8,11a-pentamethyl-icosahydro-cyclopenta[a]chrysene
-
-
one of the three major products, yield 29.4%, NMR spectroscopic analysis
-
?
(E,E,E,E)-2,6,10,15,23-pentamethyltetracosa-2,6,10,14,18,22-hexaene
3-Isopropenyl-5a,5b,8,8,13b-pentamethyl-icosahydro-cyclopenta[a]chrysene
-
-
one of the three major products, yield 34.8%, NMR spectroscopic analysis
-
?
(E,Z)-homofarnesol
(4Z,7aS,11aS)-5,8,8,11a-tetramethyl-2,3,6,7,7a,8,9,10,11,11a-decahydrobenzo[b]oxonine + 9-epi-ambrox
-
-
-
?
(R)-citronellal + H2O
(-)-isopulegol + (+)-neoiso-isopulegol
-
-
-
-
?
(S)-6,7-epoxygeraniol + H2O
(1S,3R)-3-(hydroxymethyl)-2,2-dimethyl-4-methylidenecyclohexan-1-ol
0.57% conversion with high enzyme concentrations
-
-
?
(S)-citronellal + H2O
(+)-isopulegol
-
-
-
-
?
(S)-citronellal + H2O
(-)-iso-isopulegol
0.59% conversion with high enzyme concentrations
-
-
?
10-ethylsqualene
(2R)-2-[(7E,11E)-3-ethyl-8,12,16-trimethylheptadeca-7,11,15-trien-1-yl]-1,1-dimethyl-3-methylidenecyclohexane + (3R,5aR,9aS)-3-[(5Z)-6,10-dimethylundeca-5,9-dien-2-yl]-3-ethyl-6,6,9a-trimethyl-2,3,5,5a,6,7,8,9,9a,9b-decahydro-1H-cyclopenta[a]naphthalene + (4aS,5R,8aR)-6-ethylidene-1,1,4a-trimethyl-5-[(3E,7E)-4,8,12-trimethyltrideca-3,7,11-trien-1-yl]decahydronaphthalene + (4aR,5S,8aR)-6-ethyl-1,1,4a-trimethyl-5-[(3E,7E)-4,8,12-trimethyltrideca-3,7,11-trien-1-yl]decahydronaphthalene + (2R)-2-[(3E,7E,11E)-3-ethyl-8,12,16-trimethylheptadeca-3,7,11,15-tetraen-1-yl]-1,3,3-trimethylcyclohexanol
-
-
-
-
?
15-ethylsqualene
(2R)-2-[(3E,11E)-8-ethyl-3,12,16-trimethylheptadeca-3,7,11,15-tetraen-1-yl]-1,1-dimethyl-3-methylidenecyclohexane + (4aS,5S,8aR)-5-[(7E)-4-ethyl-8,12-dimethyltrideca-3,7,11-trien-1-yl]-1,1,4a-trimethyl-6-methylidenedecahydronaphthalene + (4aS,5S,8aR)-5-[(7E)-4-ethyl-8,12-dimethyltrideca-3,7,11-trien-1-yl]-1,1,4a,6-tetramethyl-1,2,3,4,4a,5,8,8a-octahydronaphthalene + (2R)-2-[(3E,11E)-8-ethyl-3,12,16-trimethylheptadeca-3,7,11,15-tetraen-1-yl]-1,3,3-trimethylcyclohexanol
-
-
-
-
?
19-ethylsqualene
(2R)-2-[(3E,7E,11E)-12-ethyl-3,8,16-trimethylheptadeca-3,7,11,15-tetraen-1-yl]-1,1-dimethyl-3-methylidenecyclohexane + (6R)-6-[(3E,7E,11E)-12-ethyl-3,8,16-trimethylheptadeca-3,7,11,15-tetraen-1-yl]-1,5,6-trimethylcyclohexene + (4aS,5S,8aR)-5-[(3E,7E)-8-ethyl-4,12-dimethyltrideca-3,7,11-trien-1-yl]-1,1,4a-trimethyl-6-methylidenedecahydronaphthalene + (5R,8R,9R,10S,14S)-4,4,8,10,14-pentamethyl-17-(7-methyloct-6-en-3-yl)-2,3,4,5,6,7,8,9,10,11,12,14,15,16-tetradecahydro-1H-cyclopenta[a]phenanthrene + (4aS,5S,8aR)-5-[(3E,7E)-9-ethyl-4,12-dimethyltrideca-3,7,11-trien-1-yl]-1,1,4a,6-tetramethyl-1,2,3,4,4a,5,8,8a-octahydronaphthalene + (3S,3aS,5aR,5bR,7aR,11aS,11bS,13aR,13bS)-13b-ethyl-5a,5b,8,8,11a-pentamethyl-3-(prop-1-en-2-yl)icosahydro-1H-cyclopenta[a]chrysene
-
-
-
-
?
2-((2E,6E)-3,7,11-trimethyldodeca-2,6,10-trienyl)phenol + H2O
(3S,4aR,6aR,12aR,12bS)-4,4,6a,12b-tetramethyl-1,3,4,4a,5,6,6a,12,12a,12b-decahydro-2H-benzo[a]xanthen-3-ol + 2 H+
-
-
-
-
?
2-((2E,6E)-9-(3,3-dimethyloxiran-2-yl)-3,7-dimethylnona-2,6-dienyl)phenol
(4aS,6aR,12aR,12bS)-4,4,6a,12b-tetramethyl-1,3,4,4a,5,6,6a,12,12a,12b-decahydro-2H-benzo[a]xanthene + 2-[[(1S,4aS,8aS)-2,5,5,8a-tetramethyl-1,4,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]methyl]phenol + 2-[[(1S,4aS,8aS)-5,5,8a-trimethyl-2-methylidenedecahydronaphthalen-1-yl]methyl]phenol
-
-
-
-
?
2-(farnesyldimethylallyl)pyrrole
?
-
-
product is a 10:1 mixture of a tricyclic and a bicyclic unnatural polyprenoid
-
?
3,7,11-trimethyldodeca-1,6,10-trien-3-ol
(-)-caparrapioxide + (-)-8-epi-caparrapioxide
-
-
-
-
?
3-(farnesyldimethylallyl)indole
?
-
-
conversion into a 2:1 mixture of a tetracyclic and a pentacyclic product
-
?
6,7-epoxygeraniol
?
-
-
-
?
beta-pinene + H2O
alpha-pinene + terpinolene + 1-methyl-4-(propan-2-yl)cyclohexa-1,3-diene + camphene + 2-(4-methylcyclohexa-1,3-dien-1-yl)propan-2-ol + limonene
-
-
-
?
C33 polyprene
?
-
the enzymatic products consist of mono-, bi-, tri-, tetra- and pentacyclic skeletons, however, hexacyclic products are not generated
-
-
?
citronellal + H2O
isopulegol + neo-isopulegol + iso-isopulegol
-
-
-
?
farnesol
drimenol + albicanol + driman-8,11-diol + [(1S,2R,8aS)-2,5,5,8a-tetramethyl-2-[[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl]oxy]decahydronaphthalen-1-yl]methanol
-
-
drimane-type sequiterpenes
-
?
farnesyl phenyl ether
(4aS,5S,8aS)-1,1,4a,6-tetramethyl-5-(phenoxymethyl)-1,2,3,4,4a,5,8,8a-octahydronaphthalene + (4aS,4bR,10bR,12aS)-1,1,4a,10b-tetramethyl-2,3,4,4a,4b,5,10b,11,12,12a-decahydro-1H-naphtho[1,2-c]chromene
farnesylacetone
sclareoloxide
geraniol + H2O
gamma-cyclogeraniol + cyclogeraniol hydrate
0.4% conversion with high enzyme concentrations
-
-
?
geranyl phenyl ether
(6aS,10aS)-7,7,10a-trimethyl-6a,7,8,9,10,10a-hexahydro-6H-benzo[c]chromene
geranylacetone
(8aS)-2,5,5,8a-tetramethyl-4a,5,6,7,8,8a-hexahydro-4H-chromene
geranylfarnesol
?
-
-
-
-
?
geranylfarnesyl acetate
?
-
-
-
-
?
geranylgeranyl phenyl ether
(14b)-8,13-dimethyl-14-(phenoxymethyl)podocarp-12-ene + (14b)-8-methyl-13-methylidene-14-(phenoxymethyl)podocarpane
-
-
-
?
homofarnesoic acid
sclareolide
hongoquercin A
?
-
-
-
-
?
hongoquercin B
?
-
-
-
-
?
squalene
hop-22(29)-ene + hopanol
squalene
hopene
-
-
-
-
?
squalene + H2O
hopan-22-ol
additional information
?
-
citronellal
isopulegol
YP3187836
activity of mutant F481C, not of the wild-type enzyme
i.e. 2-isopropenyl-5-methyl-cyclohexanol
-
?
citronellal
isopulegol
-
-
i.e. 2-isopropenyl-5-methyl-cyclohexanol
-
?
citronellal
isopulegol
activity of mutant Y420C, not of the wild-type enzyme
i.e. 2-isopropenyl-5-methyl-cyclohexanol
-
?
citronellal
isopulegol
activity of mutant Y420C, not of the wild-type enzyme
i.e. 2-isopropenyl-5-methyl-cyclohexanol
-
?
citronellal
isopulegol
-
activity of mutant F447C, not of the wild-type enzyme
i.e. 2-isopropenyl-5-methyl-cyclohexanol
-
?
citronellal
isopulegol
activity of mutant F449C, not of the wild-type enzyme
i.e. 2-isopropenyl-5-methyl-cyclohexanol
-
?
citronellal
isopulegol
-
-
i.e. 2-isopropenyl-5-methyl-cyclohexanol
-
?
citronellal
isopulegol
-
i.e. 2-isopropenyl-5-methyl-cyclohexanol
-
?
citronellal
isopulegol
-
i.e. 2-isopropenyl-5-methyl-cyclohexanol
-
?
citronellal
isopulegol
activity of mutant F438C, not of the wild-type enzyme
i.e. 2-isopropenyl-5-methyl-cyclohexanol
-
?
citronellal
isopulegol
wild-type enzyme, and increased activity in mutant F486C
i.e. 2-isopropenyl-5-methyl-cyclohexanol
-
?
citronellal
isopulegol
activity of mutant F438C, not of the wild-type enzyme
i.e. 2-isopropenyl-5-methyl-cyclohexanol
-
?
citronellal
isopulegol
-
i.e. 2-isopropenyl-5-methyl-cyclohexanol
-
?
citronellal
isopulegol
wild-type enzyme, and increased activity in mutant F486C
i.e. 2-isopropenyl-5-methyl-cyclohexanol
-
?
citronellal
isopulegol
-
i.e. 2-isopropenyl-5-methyl-cyclohexanol
-
?
farnesyl phenyl ether
(4aS,5S,8aS)-1,1,4a,6-tetramethyl-5-(phenoxymethyl)-1,2,3,4,4a,5,8,8a-octahydronaphthalene + (4aS,4bR,10bR,12aS)-1,1,4a,10b-tetramethyl-2,3,4,4a,4b,5,10b,11,12,12a-decahydro-1H-naphtho[1,2-c]chromene
-
-
-
?
farnesyl phenyl ether
(4aS,5S,8aS)-1,1,4a,6-tetramethyl-5-(phenoxymethyl)-1,2,3,4,4a,5,8,8a-octahydronaphthalene + (4aS,4bR,10bR,12aS)-1,1,4a,10b-tetramethyl-2,3,4,4a,4b,5,10b,11,12,12a-decahydro-1H-naphtho[1,2-c]chromene
-
-
-
?
farnesylacetone
sclareoloxide
-
-
-
-
?
farnesylacetone
sclareoloxide
-
-
-
-
?
geranyl phenyl ether
(6aS,10aS)-7,7,10a-trimethyl-6a,7,8,9,10,10a-hexahydro-6H-benzo[c]chromene
-
-
-
?
geranyl phenyl ether
(6aS,10aS)-7,7,10a-trimethyl-6a,7,8,9,10,10a-hexahydro-6H-benzo[c]chromene
-
-
-
?
geranylacetone
(8aS)-2,5,5,8a-tetramethyl-4a,5,6,7,8,8a-hexahydro-4H-chromene
-
-
-
-
?
geranylacetone
(8aS)-2,5,5,8a-tetramethyl-4a,5,6,7,8,8a-hexahydro-4H-chromene
-
-
-
-
?
homofarnesoic acid
sclareolide
-
-
-
-
?
homofarnesoic acid
sclareolide
-
-
-
-
?
homofarnesol
ambroxan
-
-
-
-
?
homofarnesol
ambroxan
-
-
-
-
?
homofarnesol
ambroxan
-
-
-
?
homofarnesol
ambroxan
-
-
-
?
squalene
hop-22(29)-ene
YP3187836
-
-
-
?
squalene
hop-22(29)-ene
-
-
-
?
squalene
hop-22(29)-ene
-
-
-
?
squalene
hop-22(29)-ene
-
-
-
?
squalene
hop-22(29)-ene
-
-
-
-
?
squalene
hop-22(29)-ene
-
-
-
?
squalene
hop-22(29)-ene
-
-
-
-
?
squalene
hop-22(29)-ene
-
-
-
?
squalene
hop-22(29)-ene
-
-
-
-
?
squalene
hop-22(29)-ene
-
-
-
?
squalene
hop-22(29)-ene
-
-
-
-
?
squalene
hop-22(29)-ene
-
-
-
?
squalene
hop-22(29)-ene
-
-
hopanol is also formed
-
?
squalene
hop-22(29)-ene
-
-
the enzyme from Alicyclobacillus acidocaldarius yields pentacyclic hopene and hopanol (diplopterol) via a hopanyl cation from squalene
-
?
squalene
hop-22(29)-ene
-
products are formed in a molar ratio of hopene:hopanol, 5:1
-
-
?
squalene
hop-22(29)-ene
-
two types of water molecules ("front water" and "back waters") are involved around the deprotonation site. The two residues of Gln262 and Pro263 probably work to keep away the isopropyl group of the hopanyl cation intermediate from the "front water molecule", that is, to place the "front water" in a favorable position, leading to the minimal production of by-products, i.e., hopanol and hop-21(22)-ene. The five residues of Thr41, Glu45, Glu93, Arg127 and Trp133, by which the hydrogen-bonded network incorporating the "back waters" is constructed, increase the polarization of the "front water" to facilitate proton elimination from the isopropyl moiety of the hopanyl cation, leading to the normal product, hop-22(29)-ene
-
-
?
squalene
hop-22(29)-ene
-
products are formed in a molar ratio of hopene:hopanol, 5:1
-
-
?
squalene
hop-22(29)-ene
-
-
-
?
squalene
hop-22(29)-ene
-
-
-
?
squalene
hop-22(29)-ene
-
-
-
?
squalene
hop-22(29)-ene
Q81YD8
-
-
-
?
squalene
hop-22(29)-ene
-
-
-
-
?
squalene
hop-22(29)-ene
-
-
-
?
squalene
hop-22(29)-ene
-
-
-
?
squalene
hop-22(29)-ene
-
-
-
-
?
squalene
hop-22(29)-ene
-
-
-
-
?
squalene
hop-22(29)-ene
-
-
-
?
squalene
hop-22(29)-ene
-
-
-
-
?
squalene
hop-22(29)-ene
-
-
-
-
?
squalene
hop-22(29)-ene
-
-
-
?
squalene
hop-22(29)-ene
-
-
-
-
?
squalene
hop-22(29)-ene
-
-
-
-
?
squalene
hop-22(29)-ene
-
-
-
?
squalene
hop-22(29)-ene
-
-
-
?
squalene
hop-22(29)-ene
-
-
-
-
?
squalene
hop-22(29)-ene
-
-
-
-
?
squalene
hop-22(29)-ene
-
-
-
-
?
squalene
hop-22(29)-ene
-
-
-
?
squalene
hop-22(29)-ene
-
-
-
?
squalene
hop-22(29)-ene
-
-
-
?
squalene
hop-22(29)-ene + hopanol
-
the enzyme catalyzes cyclization of the linear triterpenoid squalene to hopene and hopanol by the class II mechanism
-
-
?
squalene
hop-22(29)-ene + hopanol
-
-
-
?
squalene
hop-22(29)-ene + hopanol
-
the enzyme catalyzes cyclization of the linear triterpenoid squalene to hopene and hopanol by the class II mechanism
-
-
?
squalene
hop-22(29)-ene + hopanol
-
-
-
?
squalene + H2O
hopan-22-ol
-
-
-
-
?
squalene + H2O
hopan-22-ol
-
-
-
?
squalene + H2O
hopan-22-ol
-
-
-
?
squalene + H2O
hopan-22-ol
-
-
-
?
additional information
?
-
YP3187836
no activity with citronellal or isopulegol (2-isopropenyl-5-methyl-cyclohexanol)
-
-
?
additional information
?
-
-
substrate specificity, overview
-
-
?
additional information
?
-
substrate specificity, overview
-
-
?
additional information
?
-
-
mutations lead to altered product pattern
-
-
?
additional information
?
-
-
mutations lead to altered product pattern
-
-
?
additional information
?
-
-
mutations lead to altered product pattern
-
-
?
additional information
?
-
-
mutations lead to altered product pattern
-
-
?
additional information
?
-
-
overview of cyclization products of wild type and mutant enzymes
-
-
?
additional information
?
-
-
overview of cyclization products of wild type and mutant enzymes
-
-
?
additional information
?
-
-
(E,E,E,E)-2,6,11,14,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene: no detectable enzymatic activity
-
-
?
additional information
?
-
-
no enzymatic cyclization of 3-(geranylgeranyl)indole
-
-
?
additional information
?
-
-
no substrate: 2-(geranylgeranyl)pyrrole
-
-
?
additional information
?
-
no activity with citronellal or isopulegol (2-isopropenyl-5-methyl-cyclohexanol)
-
-
?
additional information
?
-
-
enzyme substrate specificity in polycyclization reactions, overview
-
-
?
additional information
?
-
-
no activity with linalool and pseudoionone
-
-
?
additional information
?
-
-
the enzyme also catalyzes 2,3-oxidosqualene cyclization, but no tetrahymanol formation. Substrate specificity, detailed overview
-
-
?
additional information
?
-
the enzyme also catalyzes 2,3-oxidosqualene cyclization, but no tetrahymanol formation. Substrate specificity, detailed overview
-
-
?
additional information
?
-
-
the enzyme shows substrate diversity for polycyclization reactions, since squalene-hopene cyclases specifically address and protonate terminal double bonds of linear terpenoids, molecules with functional groups like carboxylic acids or amides can be used as substrates, overview. It is active with squalene, a C-35 squalene analogue substrate, farnesol, and geranyl geraniol, but not with geraniol, products overview
-
-
?
additional information
?
-
-
product pattern of alternative substrates, overview
-
-
?
additional information
?
-
product pattern of alternative substrates, overview
-
-
?
additional information
?
-
-
no activity with 6-ethylsqualene
-
-
?
additional information
?
-
no activity with citronellal or isopulegol (2-isopropenyl-5-methyl-cyclohexanol)
-
-
?
additional information
?
-
no activity with geraniol
-
-
?
additional information
?
-
Q81YD8
no activity with citronellal or isopulegol (2-isopropenyl-5-methyl-cyclohexanol)
-
-
?
additional information
?
-
-
no activity with citronellal or isopulegol (2-isopropenyl-5-methyl-cyclohexanol)
-
-
?
additional information
?
-
-
the enzyme also catalyzes 2,3-oxidosqualene cyclization, but no tetrahymanol formation. Substrate specificity, detailed overview
-
-
?
additional information
?
-
no activity with citronellal or isopulegol (2-isopropenyl-5-methyl-cyclohexanol)
-
-
?
additional information
?
-
no activity with citronellal or isopulegol (2-isopropenyl-5-methyl-cyclohexanol)
-
-
?
additional information
?
-
no activity with citronellal or isopulegol (2-isopropenyl-5-methyl-cyclohexanol)
-
-
?
additional information
?
-
no activity with citronellal or isopulegol (2-isopropenyl-5-methyl-cyclohexanol)
-
-
?
additional information
?
-
-
the enzyme does not catalyze 2,3-oxidosqualene cyclization nor tetrahymanol formation. Substrate specificity, detailed overview
-
-
?
additional information
?
-
-
no activity with citronellal or isopulegol (2-isopropenyl-5-methyl-cyclohexanol)
-
-
?
additional information
?
-
-
the enzyme does not catalyze tetrahymanol formation. Substrate specificity, detailed overview
-
-
?
additional information
?
-
no activity with citronellal or isopulegol (2-isopropenyl-5-methyl-cyclohexanol)
-
-
?
additional information
?
-
-
hydroxysqualene is a poor substrate
-
-
?
additional information
?
-
-
hydroxysqualene is a poor substrate
-
-
?
additional information
?
-
-
substrate specificity, detailed overview
-
-
?
additional information
?
-
no activity with citronellal or isopulegol (2-isopropenyl-5-methyl-cyclohexanol)
-
-
?
additional information
?
-
-
no activity with citronellal or isopulegol (2-isopropenyl-5-methyl-cyclohexanol)
-
-
?
additional information
?
-
-
the enzyme also catalyzes 2,3-oxidosqualene cyclization, substrate specificity, detailed overview
-
-
?
additional information
?
-
-
enzyme produces a wide variety of products due to lack of specificity
-
-
?
additional information
?
-
no activity with citronellal or isopulegol (2-isopropenyl-5-methyl-cyclohexanol)
-
-
?
additional information
?
-
no activity with citronellal or isopulegol (2-isopropenyl-5-methyl-cyclohexanol)
-
-
?
additional information
?
-
-
no activity with linalool and pseudoionone
-
-
?
additional information
?
-
-
substrate specificity, detailed overview
-
-
?
additional information
?
-
substrate specificity, overview. No activity with prenyl phenyl ether
-
-
?
additional information
?
-
ZmoSHC1 shows cyclization of the non-natural substrates homofarnesol (C16) and citronellal (C10) in addition to hopene formation from squalene, substrate specificity, overview. ZmoSHC1 exhibits a shift of activity towards substrates of shorter chain lengths, displaying over 50fold higher conversion of homofarnesol and more than 2fold higher conversion of citronellal in comparison to squalene conversion
-
-
?
additional information
?
-
no activity with citronellal or isopulegol (2-isopropenyl-5-methyl-cyclohexanol)
-
-
?
additional information
?
-
ZmoSHC1 shows cyclization of the non-natural substrates homofarnesol (C16) and citronellal (C10) in addition to hopene formation from squalene, substrate specificity, overview. ZmoSHC1 exhibits a shift of activity towards substrates of shorter chain lengths, displaying over 50fold higher conversion of homofarnesol and more than 2fold higher conversion of citronellal in comparison to squalene conversion
-
-
?
additional information
?
-
substrate specificity, overview. No activity with prenyl phenyl ether
-
-
?
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(18E)-29-methylidenehexanor-2,3-oxidosqualene
-
IC50 0.2 microMol, pH 6.0, 55°C
(1E,3E,7E,11E)-15,16-epoxy-8,12,16-trimethyl-1-methylthio-1,3,7,11-heptadecatetraene
-
IC50 1 microMol, pH 6.0, 55°C
(1E,3E,7E,11E,15E)-19,20-epoxy-7,12,16,20-tetramethyl-1-methylthio-1,3,7,11,15-heneicosapentaene
-
IC50 1.4 microMol, pH 6.0, 55°C, not time-dependency up to 10fold higher concentration than IC50
(1Z,3E,7E,11E)-15,16-epoxy-8,12,16-trimethyl-1-methylthio-1,3,7,11-heptadecatetraene
-
IC50 4 microMol, pH 6.0, 55°C
(1Z,3E,7E,11E,15E)-19,20-epoxy-7,12,16,20-tetramethyl-1-methylthio-1,3,7,11,15-heneicosapentaene
-
IC50 1.8 microMol, pH 6.0, 55°C, not time-dependency up to 10fold higher concentration than IC50
(2E)-4-[4-(6-bromo-1,2-benzisothiazol-3-yl)phenoxy]-N-methyl-N-prop-2-en-1-ylbut-2-en-1-aminium
-
-
(2E)-4-[4-[(4-bromophenyl)carbonyl]phenoxy]-N-methyl-N-prop-2-en-1-ylbut-2-en-1-aminium
-
-
(2E)-4-[[3-(4-bromophenyl)-1,2-benzisoxazol-6-yl]oxy]-N-methyl-N-prop-2-en-1-ylbut-2-en-1-aminium
-
-
(2E)-4-[[3-(4-bromophenyl)-1-benzofuran-6-yl]oxy]-N-methyl-N-prop-2-en-1-ylbut-2-en-1-aminium
-
-
(2E)-4-[[3-(4-bromophenyl)-1-benzothiophen-6-yl]oxy]-N-methyl-N-prop-2-en-1-ylbut-2-en-1-aminium
-
-
(3E,7E,11E)-15,16-epoxy-8,12,16-trimethyl-1-phenylthio-1,3,7,11-heptadecatetraene
-
IC50 2.2 microMol, pH 6.0, 55°C
(4-(2-[(allyl-cyclopropyl-amino)-methyl]-cyclopropylmethoxy)-phenyl)-(4-bromo-phenyl)-methanone
IC50 59 nM
(4-bromo-phenyl)-(4-(2-[(cyclopropyl-methyl-amino)-methyl]-cyclopropylmethoxy)-2-fluoro-phenyl)-methanone
IC50 50 nM
(4-bromo-phenyl)-(4-(2-[(cyclopropyl-methyl-amino)-methyl]-cyclopropylmethoxy)-phenyl)-methanone
IC50 62 nM
(4-bromo-phenyl)-(4-[4-(cyclopropyl-methyl-amino)-but-2-enyloxy]-phenyl)-methanone
IC50 18 nM
(4-bromo-phenyl)-(4-[6-(cyclopropyl-methyl-amino)-hexyloxy]-2-fluoro-phenyl)-methanone
IC50 38 nM
(4-chloro-phenyl)-(4-[4-(4,5-dihydro-oxazol-2-yl)-benzylidene]-piperidin-1-yl)-methanone
IC50 2800 nM
(4-[6-(allyl-methyl-amino)-hexyloxy]-2-fluoro-phenyl)-(4-bromo-phenyl)-methanone
IC50 60 nM
(4-[6-(allyl-methyl-amino)-hexyloxy]-phenyl)-(4-bromo-phenyl)-methanone
IC50 96 nM
(5-hydroxycarvacryl)trimethylammonium chloride 1-piperidine carboxylate
(5E,9E)-13,14-epoxy-6,10,14-trimethyl-1-phenylthio-1,5,9-pentadecatriene
-
IC50 7 microMol, pH 6.0, 55°C
(5E,9E,13E)-17,18-epoxy-5,10,14,18-tetramethyl-1-phenylthio-1,5,9,13-nonadecatetraene
-
IC50 3 microMol, pH 6.0, 55°C
1-(4-(4-[(4-chloro-phenoxycarbonyl)-methyl-amino]-cyclohexyl)-benzyl)-1-hydroxy-piperidinium
IC50 123 nM
1-[(4-chlorophenyl)carbonyl]-4-[[4-(4,5-dihydro-1,3-oxazol-2-yl)phenyl]methylidene]piperidine
-
-
1-[4-(trans-4-[[(4-chlorophenoxy)carbonyl](methyl)amino]cyclohexyl)benzyl]piperidinium
-
-
3-(10'-(allylmethylamino)decanoyl)chroman-2,4-dione
-
IC50 100 microMol
3-carboxy-4-nitrophenyl-dithio-1,1',2-trisnorsqualene
-
covalently modifies C435
4'-[4-(allyl-methyl-amino)-but-2-enyloxy]-biphenyl-4-yl-(4-bromo-phenyl)-methanone
IC50 29 nM
4-chlorophenyl methyl(trans-4-[4-[(1-oxidopiperidin-1-yl)methyl]phenyl]cyclohexyl)carbamate
-
-
4-[4-(allyl-methyl-amino)-but-2-enyloxy]-phenyl-(4-bromo-phenyl)-methanone
IC50 40 nM
4-[6-(allyl-methyl-amino)-hexyloxy]-piperidin-1-yl-(4-fluoro-phenyl)-methanone
IC50 1200 nM
4-[6-(cyclopropyl-methyl-amino)-hexyloxy]-piperidin-1-yl-(4-fluoro-phenyl)-methanone
IC50 760 nM
6-([1-[(4-fluorophenyl)carbonyl]piperidin-4-yl]oxy)-N-methyl-N-prop-2-en-1-ylhexan-1-aminium
-
-
6-[(1,3-dimethyl-1H-indazol-5-yl)oxy]-N-methyl-N-prop-2-en-1-ylhexan-1-aminium
-
-
6-[4-(6-bromo-1,2-benzisothiazol-3-yl)phenoxy]-N-methyl-N-prop-2-en-1-ylhexan-1-aminium
-
-
6-[4-[(4-bromophenyl)carbonyl]-3-fluorophenoxy]-N-methyl-N-prop-2-en-1-ylhexan-1-aminium
-
-
6-[4-[(4-bromophenyl)carbonyl]phenoxy]-N-(3-hydroxypropyl)-N-methylhexan-1-aminium
-
-
6-[4-[(4-bromophenyl)carbonyl]phenoxy]-N-methyl-N-prop-2-en-1-ylhexan-1-aminium
-
-
6-[[1-(4-bromophenyl)isoquinolin-6-yl]oxy]-N-methyl-N-prop-2-en-1-ylhexan-1-aminium
-
-
6-[[3-(4-bromophenyl)-1,2-benzisothiazol-5-yl]oxy]-N-methyl-N-prop-2-en-1-ylhexan-1-aminium
-
-
6-[[3-(4-bromophenyl)-1,2-benzisoxazol-6-yl]oxy]-N-methyl-N-prop-2-en-1-ylhexan-1-amine
-
6-[[3-(4-bromophenyl)-1,2-benzisoxazol-6-yl]oxy]-N-methyl-N-prop-2-en-1-ylhexan-1-aminium
-
-
6-[[3-(4-bromophenyl)-1-benzofuran-6-yl]oxy]-N-methyl-N-prop-2-en-1-ylhexan-1-amine
-
6-[[3-(4-bromophenyl)-1-benzofuran-6-yl]oxy]-N-methyl-N-prop-2-en-1-ylhexan-1-aminium
-
-
6-[[3-(4-bromophenyl)-1-methyl-1H-indol-6-yl]oxy]-N-methyl-N-prop-2-en-1-ylhexan-1-amine
-
6-[[3-(4-bromophenyl)-1H-indazol-6-yl]oxy]-N-methyl-N-prop-2-en-1-ylhexan-1-amine
-
6-[[3-(4-bromophenyl)-1H-indazol-6-yl]oxy]-N-methyl-N-prop-2-en-1-ylhexan-1-aminium
-
-
6-[[4-(4-bromophenyl)-1H-2,3-benzoxazin-7-yl]oxy]-N-methyl-N-prop-2-en-1-ylhexan-1-aminium
-
-
7-(10'-(dimethylamino-N-decyloxy))chromen-2-one
-
IC50 5 microMol
7-(10-(allylmethylamino)-decyloxy)chromen-2-one
-
IC50 2 microMol
7-(4'-(N,N,N'-trimethylethylendiamino)-but-2-ynyloxy)chromen-2-one
-
not active at 100 microMol
7-(4'-(N-diethylamino)-but-2-ynyloxy)chromen-2-one
-
IC50 5 microMol
7-(4'-(N-pyrrolidyn)-but-2-ynyloxy)chromen-2-one
-
IC50 5 microMol
7-(4-allylmethylamino-but-2-ynyloxy)chromen-2-one
-
IC50 0.75 microMol
7-(6'-(benzylamino-hexyloxy))chromen-2-one
-
IC50 8 microMol
7-(6-(allylmethylamino)-hexyloxy)chromen-2-one
-
IC50 4-5 microMol
7-(8'-(dimethylamino-N-octyloxy))chromen-2-one
-
IC50 5-7 microMol
7-(morpholinyl-N-hexyloxy)chromen-2-one
-
IC50 6 microMol
7-(morpholinyl-N-octyloxy)chromen-2-one
-
IC50 7 microMol
7-(piperidinyl-N-hexyloxy)chromen-2-one
-
IC50 8 microMol
allyl-(4-[3-(4-bromo-phenyl)-5-fluoro-1-methyl-1H-indazol-6-yloxy]-but-2-enyl)-methyl-amine
IC50 281 nM; IC50 332 nM
allyl-(4-[3-(4-bromo-phenyl)-benzofuran-6-yloxy]-but-2-enyl)-methyl-amine
IC50 23 nM
allyl-(4-[3-(4-bromo-phenyl)-benzo[b]thiophen-6-yloxy]-butyl)-methyl-amine
IC50 75 nM
allyl-(4-[3-(4-bromo-phenyl)-benzo[d]isoxazol-6-yloxy]-but-2-enyl)-amine
IC50 49 nM
allyl-(4-[4-(6-bromo-benzo[d]isothiazol-3-yl)-phenoxy]-but-2-enyl)-methyl-amine
IC50 130 nM
allyl-(6-[1-(4-bromo-phenyl)-isoquinolin-6-yloxy]-hexyl)-methyl-amine
IC50 186 nM
allyl-(6-[3-(4-bromo-phenyl)-1-methyl-1H-indazol-6-yloxy]-hexyl)-methyl-amine
IC50 289 nM
allyl-(6-[3-(4-bromo-phenyl)-1H-indazol-6-yloxy]-hexyl)-methyl-amine
IC50 180 nM
allyl-(6-[3-(4-bromo-phenyl)-benzofuran-6-yloxy]-hexyl)-methyl-amine
IC50 80 nM
allyl-(6-[3-(4-bromo-phenyl)-benzo[d]isothiazol-6-yloxy]-hexyl)-methyl-amine
IC50 306 nM
allyl-(6-[3-(4-bromo-phenyl)-benzo[d]isoxazol-6-yloxy]-hexyl)-methyl-amine
IC50 75 nM
allyl-(6-[4-(4-bromo-phenyl)-1H-benzo[d][1,2]oxazin-7-yloxy]-hexyl)-methyl-amine
IC50 172 nM
allyl-(6-[4-(6-bromo-benzo[d]isothiazol-3-yl)-phenoxy]-hexyl)-methyl-amine
IC50 141 nM
azasqualene
-
inhibition at 0.001 mM
Cu2+
-
slight inhibition at 1 mM
diethyldicarbonate
-
92% inhibition at 5 mM
dodecyldimethylamine N-oxide
-
competitive inhibition
dodecyltrimethylammonium bromide
-
competitive inhibition, 50% inhibition at 0.0001 mM
farnesol
-
inhibition at 0.1 mM
Fe2+
-
slight inhibition at 1 mM
HECAMEG
-
80% inactivation compared to CHAPS
methyl-[4-(4-piperidin-1-ylmethyl-phenyl)-cyclohexyl]-carbamic acid 4-chloro-phenyl ester
IC50 406 nM
N,N-dimethyldodecylamine N-oxide
-
forms a complex with the enzyme
N-(6-[4-[(4-bromophenyl)carbonyl]-3-fluorophenoxy]hexyl)-N-methylcyclopropanaminium
-
-
N-([4'-[(4-bromophenyl)carbonyl]biphenyl-4-yl]methyl)-N-methylprop-2-en-1-aminium
-
-
N-dodecyliodoacetamide
-
IC50 wild-type >200 microMol, quintuple mutant >200 microMol, sextuple mutant >200 microMol, pH 6.0, 50°C
N-ethylmaleimide
-
65% inhibition at 5 mM, 20% inhibition at 1 mM
N-squalenyliodoacetamide
-
IC50 wild-type >200 microMol, quintuple mutant >200 microMol, sextuple mutant 50 microMol, pH 6.0, 50°C
N-[(2E)-4-[4-[(4-bromophenyl)carbonyl]phenoxy]but-2-en-1-yl]-N-methylcyclopropanaminium
-
-
N-[6-([1-[(4-fluorophenyl)carbonyl]piperidin-4-yl]oxy)hexyl]-N-methylcyclopropanaminium
-
-
N-[[(1S,2S)-2-([4-[(4-bromophenyl)carbonyl]-3-fluorophenoxy]methyl)cyclopropyl]methyl]-N-methylcyclopropanaminium
-
-
N-[[(1S,2S)-2-([4-[(4-bromophenyl)carbonyl]phenoxy]methyl)cyclopropyl]methyl]-N-methylcyclopropanaminium
-
-
N-[[(1S,2S)-2-([4-[(4-bromophenyl)carbonyl]phenoxy]methyl)cyclopropyl]methyl]-N-prop-2-en-1-ylcyclopropanaminium
-
-
octylthiogucopyranoside
-
complete inactivation
p-chloromercuribenzenesulfonic acid
-
96% inhibition at 1 mM
Ro 48-8071
-
IC50 0.35 microMol
sodium dodecylsulfate
-
strong inhibition
sodium taurodeoxycholate
-
under 0.15% and above 0.25%
squalene-maleimide
-
time-dependent inhibitor
taurodeoxycholate
-
80% inactivation compared to CHAPS
Triton-X100
-
96% inhibition
Zn2+
-
slight inhibition at 5 mM
Zwittergent
-
80% inactivation compared to CHAPS
-
(5-hydroxycarvacryl)trimethylammonium chloride 1-piperidine carboxylate
-
i.e. AMO 1618, competitive inhibition
(5-hydroxycarvacryl)trimethylammonium chloride 1-piperidine carboxylate
-
99% inhibition at 1 mM
additional information
-
vinyl sulfide and ketene dithioacetal derivates of truncated 2,3-ocidosqualene interact with active site of the enzyme
-
additional information
-
sulfur-substituted oxidosqualene analogues serve as inhibitors
-
additional information
-
effect of thiol-modifying inhibitors on mutant enzymes
-
additional information
-
inhibition by n-alkyldimethylammoniumhalides with alkyl chain lengths between 12 and 18 C atoms, inhibition increases with decreasing chain length
-
additional information
-
sulfur-containing analogues of 2,3-oxidosqualene inhibit enzyme activity, 50% inhibition at concentrations in the nanomolar range
-
additional information
inhibitors designed as cholesterol-lowering agents, for 11 inhibitors the structures of the enzyme-inhibitor complexes were determined by X-ray crystallography
-
additional information
-
inhibitors designed as cholesterol-lowering agents, for 11 inhibitors the structures of the enzyme-inhibitor complexes were determined by X-ray crystallography
-
additional information
-
several detergents have inhibitory effect
-
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0.0002
(18E)-29-methylidenehexanor-2,3-oxidosqualene
Alicyclobacillus acidocaldarius
-
IC50 0.2 microMol, pH 6.0, 55°C
0.001
(1E,3E,7E,11E)-15,16-epoxy-8,12,16-trimethyl-1-methylthio-1,3,7,11-heptadecatetraene
Alicyclobacillus acidocaldarius
-
IC50 1 microMol, pH 6.0, 55°C
0.0014
(1E,3E,7E,11E,15E)-19,20-epoxy-7,12,16,20-tetramethyl-1-methylthio-1,3,7,11,15-heneicosapentaene
Alicyclobacillus acidocaldarius
-
IC50 1.4 microMol, pH 6.0, 55°C, not time-dependency up to 10fold higher concentration than IC50
0.004
(1Z,3E,7E,11E)-15,16-epoxy-8,12,16-trimethyl-1-methylthio-1,3,7,11-heptadecatetraene
Alicyclobacillus acidocaldarius
-
IC50 4 microMol, pH 6.0, 55°C
0.0018
(1Z,3E,7E,11E,15E)-19,20-epoxy-7,12,16,20-tetramethyl-1-methylthio-1,3,7,11,15-heneicosapentaene
Alicyclobacillus acidocaldarius
-
IC50 1.8 microMol, pH 6.0, 55°C, not time-dependency up to 10fold higher concentration than IC50
0.0022
(3E,7E,11E)-15,16-epoxy-8,12,16-trimethyl-1-phenylthio-1,3,7,11-heptadecatetraene
Alicyclobacillus acidocaldarius
-
IC50 2.2 microMol, pH 6.0, 55°C
0.000059
(4-(2-[(allyl-cyclopropyl-amino)-methyl]-cyclopropylmethoxy)-phenyl)-(4-bromo-phenyl)-methanone
Alicyclobacillus acidocaldarius
IC50 59 nM
0.00005
(4-bromo-phenyl)-(4-(2-[(cyclopropyl-methyl-amino)-methyl]-cyclopropylmethoxy)-2-fluoro-phenyl)-methanone
Alicyclobacillus acidocaldarius
IC50 50 nM
0.000062
(4-bromo-phenyl)-(4-(2-[(cyclopropyl-methyl-amino)-methyl]-cyclopropylmethoxy)-phenyl)-methanone
Alicyclobacillus acidocaldarius
IC50 62 nM
0.000018
(4-bromo-phenyl)-(4-[4-(cyclopropyl-methyl-amino)-but-2-enyloxy]-phenyl)-methanone
Alicyclobacillus acidocaldarius
IC50 18 nM
0.000038
(4-bromo-phenyl)-(4-[6-(cyclopropyl-methyl-amino)-hexyloxy]-2-fluoro-phenyl)-methanone
Alicyclobacillus acidocaldarius
IC50 38 nM
0.0028
(4-chloro-phenyl)-(4-[4-(4,5-dihydro-oxazol-2-yl)-benzylidene]-piperidin-1-yl)-methanone
Alicyclobacillus acidocaldarius
IC50 2800 nM
0.00006
(4-[6-(allyl-methyl-amino)-hexyloxy]-2-fluoro-phenyl)-(4-bromo-phenyl)-methanone
Alicyclobacillus acidocaldarius
IC50 60 nM
0.000096
(4-[6-(allyl-methyl-amino)-hexyloxy]-phenyl)-(4-bromo-phenyl)-methanone
Alicyclobacillus acidocaldarius
IC50 96 nM
0.007
(5E,9E)-13,14-epoxy-6,10,14-trimethyl-1-phenylthio-1,5,9-pentadecatriene
Alicyclobacillus acidocaldarius
-
IC50 7 microMol, pH 6.0, 55°C
0.003
(5E,9E,13E)-17,18-epoxy-5,10,14,18-tetramethyl-1-phenylthio-1,5,9,13-nonadecatetraene
Alicyclobacillus acidocaldarius
-
IC50 3 microMol, pH 6.0, 55°C
0.000123
1-(4-(4-[(4-chloro-phenoxycarbonyl)-methyl-amino]-cyclohexyl)-benzyl)-1-hydroxy-piperidinium
Alicyclobacillus acidocaldarius
IC50 123 nM
0.1
3-(10'-(allylmethylamino)decanoyl)chroman-2,4-dione
Alicyclobacillus acidocaldarius
-
IC50 100 microMol
0.000029
4'-[4-(allyl-methyl-amino)-but-2-enyloxy]-biphenyl-4-yl-(4-bromo-phenyl)-methanone
Alicyclobacillus acidocaldarius
IC50 29 nM
0.00004
4-[4-(allyl-methyl-amino)-but-2-enyloxy]-phenyl-(4-bromo-phenyl)-methanone
Alicyclobacillus acidocaldarius
IC50 40 nM
0.0012
4-[6-(allyl-methyl-amino)-hexyloxy]-piperidin-1-yl-(4-fluoro-phenyl)-methanone
Alicyclobacillus acidocaldarius
IC50 1200 nM
0.00076
4-[6-(cyclopropyl-methyl-amino)-hexyloxy]-piperidin-1-yl-(4-fluoro-phenyl)-methanone
Alicyclobacillus acidocaldarius
IC50 760 nM
0.000075
6-[[3-(4-bromophenyl)-1,2-benzisoxazol-6-yl]oxy]-N-methyl-N-prop-2-en-1-ylhexan-1-amine
Alicyclobacillus acidocaldarius
-
0.005
7-(10'-(dimethylamino-N-decyloxy))chromen-2-one
Alicyclobacillus acidocaldarius
-
IC50 5 microMol
0.002
7-(10-(allylmethylamino)-decyloxy)chromen-2-one
Alicyclobacillus acidocaldarius
-
IC50 2 microMol
0.005
7-(4'-(N-diethylamino)-but-2-ynyloxy)chromen-2-one
Alicyclobacillus acidocaldarius
-
IC50 5 microMol
0.005
7-(4'-(N-pyrrolidyn)-but-2-ynyloxy)chromen-2-one
Alicyclobacillus acidocaldarius
-
IC50 5 microMol
0.00075
7-(4-allylmethylamino-but-2-ynyloxy)chromen-2-one
Alicyclobacillus acidocaldarius
-
IC50 0.75 microMol
0.008
7-(6'-(benzylamino-hexyloxy))chromen-2-one
Alicyclobacillus acidocaldarius
-
IC50 8 microMol
0.004 - 0.005
7-(6-(allylmethylamino)-hexyloxy)chromen-2-one
Alicyclobacillus acidocaldarius
-
IC50 4-5 microMol
0.005 - 0.007
7-(8'-(dimethylamino-N-octyloxy))chromen-2-one
Alicyclobacillus acidocaldarius
-
IC50 5-7 microMol
0.006
7-(morpholinyl-N-hexyloxy)chromen-2-one
Alicyclobacillus acidocaldarius
-
IC50 6 microMol
0.007
7-(morpholinyl-N-octyloxy)chromen-2-one
Alicyclobacillus acidocaldarius
-
IC50 7 microMol
0.008
7-(piperidinyl-N-hexyloxy)chromen-2-one
Alicyclobacillus acidocaldarius
-
IC50 8 microMol
0.000281 - 0.000332
allyl-(4-[3-(4-bromo-phenyl)-5-fluoro-1-methyl-1H-indazol-6-yloxy]-but-2-enyl)-methyl-amine
0.000023
allyl-(4-[3-(4-bromo-phenyl)-benzofuran-6-yloxy]-but-2-enyl)-methyl-amine
Alicyclobacillus acidocaldarius
IC50 23 nM
0.000075
allyl-(4-[3-(4-bromo-phenyl)-benzo[b]thiophen-6-yloxy]-butyl)-methyl-amine
Alicyclobacillus acidocaldarius
IC50 75 nM
0.000049
allyl-(4-[3-(4-bromo-phenyl)-benzo[d]isoxazol-6-yloxy]-but-2-enyl)-amine
Alicyclobacillus acidocaldarius
IC50 49 nM
0.00013
allyl-(4-[4-(6-bromo-benzo[d]isothiazol-3-yl)-phenoxy]-but-2-enyl)-methyl-amine
Alicyclobacillus acidocaldarius
IC50 130 nM
0.000186
allyl-(6-[1-(4-bromo-phenyl)-isoquinolin-6-yloxy]-hexyl)-methyl-amine
Alicyclobacillus acidocaldarius
IC50 186 nM
0.000289
allyl-(6-[3-(4-bromo-phenyl)-1-methyl-1H-indazol-6-yloxy]-hexyl)-methyl-amine
Alicyclobacillus acidocaldarius
IC50 289 nM
0.00018
allyl-(6-[3-(4-bromo-phenyl)-1H-indazol-6-yloxy]-hexyl)-methyl-amine
Alicyclobacillus acidocaldarius
IC50 180 nM
0.00008
allyl-(6-[3-(4-bromo-phenyl)-benzofuran-6-yloxy]-hexyl)-methyl-amine
Alicyclobacillus acidocaldarius
IC50 80 nM
0.000306
allyl-(6-[3-(4-bromo-phenyl)-benzo[d]isothiazol-6-yloxy]-hexyl)-methyl-amine
Alicyclobacillus acidocaldarius
IC50 306 nM
0.000075
allyl-(6-[3-(4-bromo-phenyl)-benzo[d]isoxazol-6-yloxy]-hexyl)-methyl-amine
Alicyclobacillus acidocaldarius
IC50 75 nM
0.000172
allyl-(6-[4-(4-bromo-phenyl)-1H-benzo[d][1,2]oxazin-7-yloxy]-hexyl)-methyl-amine
Alicyclobacillus acidocaldarius
IC50 172 nM
0.000141
allyl-(6-[4-(6-bromo-benzo[d]isothiazol-3-yl)-phenoxy]-hexyl)-methyl-amine
Alicyclobacillus acidocaldarius
IC50 141 nM
0.000406
methyl-[4-(4-piperidin-1-ylmethyl-phenyl)-cyclohexyl]-carbamic acid 4-chloro-phenyl ester
Alicyclobacillus acidocaldarius
IC50 406 nM
0.2
N-dodecyliodoacetamide
Alicyclobacillus acidocaldarius
-
IC50 wild-type >200 microMol, quintuple mutant >200 microMol, sextuple mutant >200 microMol, pH 6.0, 50°C
0.05 - 0.2
N-squalenyliodoacetamide
0.00035
Ro 48-8071
Alicyclobacillus acidocaldarius
-
IC50 0.35 microMol
0.000281
allyl-(4-[3-(4-bromo-phenyl)-5-fluoro-1-methyl-1H-indazol-6-yloxy]-but-2-enyl)-methyl-amine
Alicyclobacillus acidocaldarius
IC50 281 nM
0.000332
allyl-(4-[3-(4-bromo-phenyl)-5-fluoro-1-methyl-1H-indazol-6-yloxy]-but-2-enyl)-methyl-amine
Alicyclobacillus acidocaldarius
IC50 332 nM
0.05
N-squalenyliodoacetamide
Alicyclobacillus acidocaldarius
-
IC50 sextuple mutant 50 microMol, pH 6.0, 50°C
0.2
N-squalenyliodoacetamide
Alicyclobacillus acidocaldarius
-
IC50 wild-type >200 microMol
0.2
N-squalenyliodoacetamide
Alicyclobacillus acidocaldarius
-
IC50 quintuple mutant >200 microMol
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F481C
YP3187836
site-directed mutagenesis, the mutant performs interconversion of citronellal and isopulegol
C25S/C50S/C435S/C455S/C537S
-
quintuple mutant
C25S/C50S/D376C/C435S/C455S/C537S
-
sextuple mutant
D376E/D377E
-
no enzyme activity
D376G
-
0.2% activity when enzyme concentration is increased to 100fold
D376Q
-
no enzyme activity
D376R
-
no enzyme activity
D377C/V380E/V381A
-
no detectable cyclization of squalene
D377E
-
0.2% activity when enzyme concentration is increased to 100fold
D377E/D376Q/D376R/D377R/E45K/W406V/W417A/D377C
D377G
-
0.2% activity when enzyme concentration is increased to 100fold
D377Q
-
0.2% activity when enzyme concentration is increased to 100fold
D377R
-
no enzyme activity
E45D
-
reduced enzyme activity
E45K
-
no enzyme activity
E45Q
-
slightly increased enzyme activity
F365G
the mutant shows increased activity with (S)-6,7-epoxygeraniol and no activity with geraniol compared to the wild type enzyme
F365Y
-
and mutant with F365 changed to unnatural amino acid O-methyltyrosine. Both show increased decreased activity at high temperature
F601W
the mutant shows about wild type activity
F605W
-
increased catalytic acitivy at low temperature, but decreased activity at high temperature due to higher cation-pi binding energies
F605Y
-
and mutant with F605 changed to unnatural amino acid O-methyltyrosine. Both show increased catalytic acitivy at low temperature, but decreased activity at high temperature due to higher cation-pi binding energies
G262A
-
the mutant produces hopanol as the main product instead of hop-22(29)-ene. The mutant also produces hop-21(22)ene
G600F
the mutant exhibits 68% conversion of geraniol to cyclogeraniol hydrate
I261W
the mutant shows increased activity with (S)-6,7-epoxygeraniol and no activity with geraniol compared to the wild type enzyme
L36A
the mutant shows increased activity with (S)-6,7-epoxygeraniol compared to the wild type enzyme
Q262A
-
mutation located between C29 of the hopanyl cation and the "front water"
S307A
the mutant shows increased activity with (S)-6,7-epoxygeraniol and no activity with geraniol compared to the wild type enzyme
W23V
-
same activity and optimal temperature as wild type enzyme
W258L
-
60% of wild type activity, lower temperature optimum
W312G
-
the mutant produces (-)-neo-isopulegol from (S)-citronellal
W406V
-
no enzyme activity
W417A
-
no enzyme activity
W485V
-
same activity and optimal temperature as wild type enzyme
W522V
-
same activity and optimal temperature as wild type enzyme
W533A
-
same activity and optimal temperature as wild type enzyme
W591L
-
same activity and optimal temperature as wild type enzyme
W78S
-
same activity and optimal temperature as wild type enzyme
Y420W
the mutant exhibits 54% conversion of (S)-6,7-epoxygeraniol to (1S,3R)-3-(hydroxymethyl)-2,2-dimethyl-4-methylidenecyclohexan-1-ol
Y420W/G600F
the mutant exhibits 78% conversion of (S)-6,7-epoxygeraniol to (1S,3R)-3-(hydroxymethyl)-2,2-dimethyl-4-methylidenecyclohexan-1-ol
Y495F
-
reduced enzyme activity, wild-type product pattern
Y606A
-
kinetics identical to wild-type
Y606A/W23V/W495V/W522V/W533A/W591L/W78S/E35Q/E197Q/D530N/T378A
Y609A
-
the mutant produces (+)-isopulegol from (S)-citronellal
Y612F
-
reduced enzyme activity, wild-type product pattern
Y612F/D376E/D376G/D377E/D377G/D377Q/E45A/E45D/F365W/T41A/E93A/R127Q/W133A/Y267A/F434A/F437A/W258L/D350N/D421N/D442N/H451R/D447N/D377N/D313N/E535Q/D374E
Y420C
-
site-directed mutagenesis, the mutant performs interconversion of citronellal and isopulegol
-
A306F
the mutant produces apolypodatetraene, gamma-polypodatetraene and neopolypoda-5(6),13,17,21-teraene from squalene and polypoda-8(9),13,17,21-tetraen-3a-ol, polypoda-7(8),13,17,21-tetraen-3alpha-ol and polypoda-7(8),13,17,21-tetraen-3beta-ol from a racemic mixture of (3S)-2,3-oxidosqualene and (3R)-2,3-oxidosqualene
A306T
the mutant produces (20R)-dammara-13(17),24-dien-3a-ol, (20R)-dammara-13(17),24-dien-3b-ol, (20R)-dammara-12(13),24-dien-3a-ol, (20R)-dammara-12(13),24-dien-3b-ol and (20R,24R)-17-epi-epoxydammarane from a racemic mixture of (3S)-2,3-oxidosqualene and (3R)-2,3-oxidosqualene
A306V
the mutant produces apolypodatetraene, dammara-13(17)-24-diene, gamma-polypodatetraene, (17E)(13aH)-malabarica-14(27),17,21-triene, (20R)-dammara-12(13),24-diene, (20R)-eupha-7(8),24-diene, (20S)-tirucalla-7(8),24-diene, and 17-epi-dammara-20(21),24-diene from squalene
F129L
the mutant shows a (E,E)-homofarnesol conversion at 24 h of reaction which is comparable to the wild type enzyme
F129L/F601Y
the mutant shows lower (E,E)-homofarnesol conversion at 24 h of reaction compared to the wild type enzyme
F129L/M132R/I432T
the mutant shows much lower (E,E)-homofarnesol conversion at 24 h of reaction compared to the wild type enzyme
F129L/M132R/I432T/F601Y
the mutant shows much lower (E,E)-homofarnesol conversion compared to the wild type enzyme
F365C
the mutant is able to convert geraniol into (S)-gamma-cyclogeraniol and cyclogeraniol hydrate
F601Y
the mutant shows a (E,E)-homofarnesol conversion at 24 h of reaction which is comparable to the wild type enzyme
G600F
the mutant is able to convert geraniol into (S)-gamma-cyclogeraniol and cyclogeraniol hydrate
I261A
the mutant exclusively converts (S)-citronellal to ( -)-iso-isopulegol isomer (1R,2S,5S)-5-methyl-2-(prop-1-en-2-yl)cyclohexan-1-ol with an 11times improved activity as compared to the wild type enzyme
L607F
the mutant produces the farnesyl ether with 6times higher yield from farnesol than the wild type enzyme
M132R/A224V/I432T
the mutant shows better (E,E)-homofarnesol conversion at 24 h of reaction compared to the wild type enzyme
M132R/I432T
the mutant shows better (E,E)-homofarnesol conversion at 24 h of reaction compared to the wild type enzyme
M132R/I432T/F601Y
the mutant shows much lower (E,E)-homofarnesol conversion at 24 h of reaction compared to the wild type enzyme
Q579H/F601Y
the mutant shows better (E,E)-homofarnesol conversion at 24 h of reaction compared to the wild type enzyme
T77A/I92V/F129L
the mutant shows better (E,E)-homofarnesol conversion at 24 h of reaction compared to the wild type enzyme
Y420W/G600F
the mutant produces selectively (1S)-3-(hydroxymethyl)-2,2-dimethyl-4-methylidenecyclohexan-1-ol from 6,7-epoxygeraniol with a conversion of up to 78%
F409C
Q81YD8
site-directed mutagenesis, the mutant does not perform interconversion of citronellal and isopulegol
F447C
-
site-directed mutagenesis, the mutant performs interconversion of citronellal and isopulegol
F436C
site-directed mutagenesis, the mutant does not perform interconversion of citronellal and isopulegol
F450C
site-directed mutagenesis, the mutant does not perform interconversion of citronellal and isopulegol
F436C
-
site-directed mutagenesis, the mutant does not perform interconversion of citronellal and isopulegol
-
F450C
-
site-directed mutagenesis, the mutant does not perform interconversion of citronellal and isopulegol
-
F445C
-
site-directed mutagenesis, the mutant does not perform interconversion of citronellal and isopulegol
F438C
site-directed mutagenesis, the mutant does not perform interconversion of citronellal and isopulegol
F457C
site-directed mutagenesis, the mutant does not perform interconversion of citronellal and isopulegol
F486C
site-directed mutagenesis, the mutant shows increased activity in interconversion of citronellal and isopulegol compared to the wild-type enzyme
W555A
site-directed mutagenesis, the mutant shows no squalene hopene cyclase activity, and low citronellal cyclase activity
W555C
site-directed mutagenesis, the mutant shows no squalene hopene cyclase activity, and low citronellal cyclase activity
W555D
site-directed mutagenesis, the mutant shows no squalene hopene cyclase activity, and moderate citronellal cyclase activity
W555E
site-directed mutagenesis, the mutant shows highly reduced squalene hopene cyclase activity, and low citronellal cyclase activity
W555G
site-directed mutagenesis, the mutant shows no squalene hopene cyclase activity, and low citronellal cyclase activity
W555H
site-directed mutagenesis, the mutant shows no squalene hopene cyclase activity, and moderate citronellal cyclase activity
W555I
site-directed mutagenesis, the mutant shows no squalene hopene cyclase activity, and low citronellal cyclase activity
W555K
site-directed mutagenesis, the mutant shows no squalene hopene cyclase activity, and low citronellal cyclase activity
W555L
site-directed mutagenesis, the mutant shows no squalene hopene cyclase activity, and low citronellal cyclase activity
W555M
site-directed mutagenesis, the mutant shows highly reduced squalene hopene cyclase activity, and low citronellal cyclase activity
W555N
site-directed mutagenesis, the mutant shows highly reduced squalene hopene cyclase activity, and moderate citronellal cyclase activity
W555P
site-directed mutagenesis, the mutant shows no squalene hopene cyclase activity, and low citronellal cyclase activity
W555Q
site-directed mutagenesis, the mutant shows highly reduced squalene hopene cyclase activity, and low citronellal cyclase activity
W555R
site-directed mutagenesis, the mutant shows no squalene hopene cyclase activity, and low citronellal cyclase activity
W555S
site-directed mutagenesis, the mutant shows no squalene hopene cyclase activity, and low citronellal cyclase activity
W555T
site-directed mutagenesis, the mutant shows no squalene hopene cyclase activity, and higher citronellal cyclase activity
W555V
site-directed mutagenesis, the mutant shows no squalene hopene cyclase activity, and low citronellal cyclase activity
F438C
-
site-directed mutagenesis, the mutant performs interconversion of citronellal and isopulegol
-
F486C
-
site-directed mutagenesis, the mutant shows increased activity in interconversion of citronellal and isopulegol compared to the wild-type enzyme
-
C435S/D374I/D374V/H451F
inactive mutant
C435S/D374I/D374V/H451F
site-directed mutagenesis, inactive mutant
D376C
-
inactive
D376E
inactive mutant
D376E
-
10% enzyme activity
D376E
site-directed mutagenesis, inactive mutant
D377C/D377N/Y612A
the mutant shows an altered product pattern compared to the wild-type enzyme, overview
D377C/D377N/Y612A
site-directed mutagenesis, the mutant shows an altered product pattern compared to the wild-type enzyme, overview
D377E/D376Q/D376R/D377R/E45K/W406V/W417A/D377C
inactive mutant
D377E/D376Q/D376R/D377R/E45K/W406V/W417A/D377C
site-directed mutagenesis, inactive mutant
E45A
-
reduced enzyme activity
E45A
-
mutation located around the "back waters"
E45A
-
production of hop-22(29)-ene is less throughout the entire temperature range than that by the wild-type. Hop-21(22)ene is not produced
E93A
-
mutation located around the "back waters"
E93A
-
production of hop-22(29)-ene is less throughout the entire temperature range than that by the wild-type. Hop-21(22)ene is not produced
F365A
the mutant shows an altered product pattern compared to the wild-type enzyme, overview
F365A
site-directed mutagenesis, the mutant shows an altered product pattern compared to the wild-type enzyme, overview
F365A
the mutant shows increased activity with geraniol and (S)-6,7-epoxygeraniol compared to the wild type enzyme
F365C
the mutant exhibits 15% conversion of geraniol to gamma-cyclogeraniol
F365C
the mutant shows increased activity with geraniol compared to the wild type enzyme
F365W
inactive
F365W
-
marginal catalytic activity
F434A
-
mutation near the substrat channel
F434A
-
production of hop-22(29)-ene is decreased, production of hopanol is markedly increased at lower temperatures
F437A
-
mutation near the substrat channel
F437A
-
production of hop-22(29)-ene is decreased, production of hopanol is markedly increased at lower temperatures
F601A
the mutant shows about wild type activity
F601A
the mutant shows an altered product pattern compared to the wild-type enzyme, overview
F601A
site-directed mutagenesis, the mutant shows an altered product pattern compared to the wild-type enzyme, overview
F605A
-
altered product pattern
F605A
the mutant shows an altered product pattern compared to the wild-type enzyme, overview
F605A
site-directed mutagenesis, the mutant shows an altered product pattern compared to the wild-type enzyme, overview
I261A
the mutant shows an altered product pattern compared to the wild-type enzyme, overview
I261A
site-directed mutagenesis, the mutant shows an altered product pattern compared to the wild-type enzyme, overview
I261A
the mutant exhibits 11% conversion of citronellal to (-)-iso-isopulegol. The mutant shows increased activity with geraniol and (S)-6,7-epoxygeraniol compared to the wild type enzyme
I261A
-
the mutant has higher activity with (S)-citronellal compared to the wild type enzyme
P263A
-
mutation located between C29 of the hopanyl cation and the "front water"
P263A
-
the mutant produces hopanol as the main product instead of hop-22(29)-ene. The mutant also produces hop-21(22)ene
P263G
-
mutation located between C29 of the hopanyl cation and the "front water"
P263G
-
the mutant produces hopanol as the main product instead of hop-22(29)-ene. The mutant also produces hop-21(22)ene
Q262G
-
mutation located between C29 of the hopanyl cation and the "front water"
Q262G
-
the mutant produces hopanol as the main product instead of hop-22(29)-ene. The mutant also produces hop-21(22)ene
Q262G/Q262A/P263G/P263A
the mutant shows an altered product pattern compared to the wild-type enzyme, overview
Q262G/Q262A/P263G/P263A
site-directed mutagenesis, the mutant shows an altered product pattern compared to the wild-type enzyme, overview
R127Q
-
mutation located around the "back waters"
R127Q
-
production of hop-22(29)-ene is less throughout the entire temperature range than that by the wild-type. Hop-21(22)ene is not produced
T41A
-
mutation located around the "back waters"
T41A
-
production of hop-22(29)-ene is less throughout the entire temperature range than that by the wild-type. Hop-21(22)ene is not produced
V380E
inactive mutant
V380E
site-directed mutagenesis, inactive mutant
V381A/D376C
inactive mutant
V381A/D376C
site-directed mutagenesis, inactive mutant
W133A
-
mutation located around the "back waters"
W133A
-
production of hop-22(29)-ene is less throughout the entire temperature range than that by the wild-type. Hop-21(22)ene is not produced
W169A
the mutant shows about wild type activity
W169A
-
the mutant has higher activity with (S)-citronellal compared to the wild type enzyme
W169F/W169H/W489A/F605K
the mutant shows an altered product pattern compared to the wild-type enzyme, overview
W169F/W169H/W489A/F605K
site-directed mutagenesis, the mutant shows an altered product pattern compared to the wild-type enzyme, overview
Y267A
-
mutation near the substrat channel
Y267A
-
production of hop-22(29)-ene is decreased, production of hopanol is markedly increased at lower temperatures
Y420A
inactive
Y420A
the mutant shows an altered product pattern compared to the wild-type enzyme, overview
Y420A
site-directed mutagenesis, the mutant shows an altered product pattern compared to the wild-type enzyme, overview
Y420C
the mutant shows about wild type activity
Y420C
site-directed mutagenesis, the mutant performs interconversion of citronellal and isopulegol
Y606A/W23V/W495V/W522V/W533A/W591L/W78S/E35Q/E197Q/D530N/T378A
the mutant shows the same product pattern and activity as the wild-type
Y606A/W23V/W495V/W522V/W533A/W591L/W78S/E35Q/E197Q/D530N/T378A
site-directed mutagenesis, the mutant shows the same product pattern and activity as the wild-type
Y609A/Y612A/L607K
the mutant shows an altered product pattern compared to the wild-type enzyme, overview
Y609A/Y612A/L607K
site-directed mutagenesis, the mutant shows an altered product pattern compared to the wild-type enzyme, overview
Y609F
-
wild type activity, altered product pattern
Y609F
the mutant shows an altered product pattern compared to the wild-type enzyme, overview
Y609F
site-directed mutagenesis, the mutant shows an altered product pattern compared to the wild-type enzyme, overview
Y609F
site-directed mutagenesis, the mutant shows an altered product pattern compared to the wild-type enzyme, overview. The phenotype of Y609F mutein is contrarily described in two publications
Y612F/D376E/D376G/D377E/D377G/D377Q/E45A/E45D/F365W/T41A/E93A/R127Q/W133A/Y267A/F434A/F437A/W258L/D350N/D421N/D442N/H451R/D447N/D377N/D313N/E535Q/D374E
the mutant shows the same product pattern as the wild-type with less enzyme activity
Y612F/D376E/D376G/D377E/D377G/D377Q/E45A/E45D/F365W/T41A/E93A/R127Q/W133A/Y267A/F434A/F437A/W258L/D350N/D421N/D442N/H451R/D447N/D377N/D313N/E535Q/D374E
site-directed mutagenesis, the mutant shows the same product pattern as the wild-type with less enzyme activity
F438C
-
site-directed mutagenesis, the mutant does not perform interconversion of citronellal and isopulegol
F438C
site-directed mutagenesis, the mutant performs interconversion of citronellal and isopulegol
W555F
site-directed mutagenesis, the mutant shows no squalene hopene cyclase activity, and higher citronellal cyclase activity
W555F
W555 is essential for hopene formation but W555Y and W555F have enhanced citronellal cyclase activity. All muteins of position W555 show abolished or strongly reduced hopene-forming activity compared to wild-type protein. W555Y is the only mutein with low but significant residual SHC activity
W555Y
site-directed mutagenesis, the mutant shows highly reduced squalene hopene cyclase activity,and higher citronellal cyclase activity
W555Y
W555 is essential for hopene formation but W555Y and W555F have enhanced citronellal cyclase activity. All muteins of position W555 show abolished or strongly reduced hopene-forming activity compared to wild-type protein. W555Y is the only mutein with low but significant residual SHC activity
W555F
-
site-directed mutagenesis, the mutant shows no squalene hopene cyclase activity, and higher citronellal cyclase activity
-
W555F
-
W555 is essential for hopene formation but W555Y and W555F have enhanced citronellal cyclase activity. All muteins of position W555 show abolished or strongly reduced hopene-forming activity compared to wild-type protein. W555Y is the only mutein with low but significant residual SHC activity
-
W555Y
-
site-directed mutagenesis, the mutant shows highly reduced squalene hopene cyclase activity,and higher citronellal cyclase activity
-
W555Y
-
W555 is essential for hopene formation but W555Y and W555F have enhanced citronellal cyclase activity. All muteins of position W555 show abolished or strongly reduced hopene-forming activity compared to wild-type protein. W555Y is the only mutein with low but significant residual SHC activity
-
additional information
-
overview
additional information
-
modification of critically located Cys residues
additional information
-
various mutations of conserved amino acid residues
additional information
-
mutations of Y609, Y495, Y612 and Y420 lead to an altered product pattern, compared to wild-type enzyme
additional information
-
replacement of F605 by mono-, di- or trifluorophenylalanine, with or without additional mutation Y606A, kinetic analysis. Mutant F605 changed to trifluorophenylalanine plus mutation Y606A has negligibly small activity
additional information
-
product patterns of mutant enzymes, detailed overview
additional information
product patterns of mutant enzymes, detailed overview
additional information
knockout of gene slr2089, phenotype and self-complementation by gene slr2089 expression
additional information
-
knockout of gene slr2089, phenotype and self-complementation by gene slr2089 expression
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-
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Alicyclobacillus acidocaldarius subsp. acidocaldarius (P33247)
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Alicyclobacillus acidocaldarius subsp. acidocaldarius DSM 446 (P33247)
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2017
Alicyclobacillus acidocaldarius
-
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24
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2018
Alicyclobacillus acidocaldarius
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Activity of squalene-hopene cyclases in bicontinuous microemulsions
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2015
Alicyclobacillus acidocaldarius
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2016
Alicyclobacillus acidocaldarius subsp. acidocaldarius DSM 446 (P33247)
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2018
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2018
Alicyclobacillus acidocaldarius
-
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Alicyclobacillus acidocaldarius (P33247)
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Alicyclobacillus acidocaldarius
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