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(2E,6E)-farnesyl diphosphate = pentalenene + diphosphate
(2E,6E)-farnesyl diphosphate = pentalenene + diphosphate
mechanism
-
(2E,6E)-farnesyl diphosphate = pentalenene + diphosphate
stereochemistry
-
(2E,6E)-farnesyl diphosphate = pentalenene + diphosphate
stereochemistry, SE reaction type
-
(2E,6E)-farnesyl diphosphate = pentalenene + diphosphate
the initial step in the reaction is probably a cyclization of farnesyl diphosphate to form humulene. The enzyme is involved in the biosynthesis of pentalenolactone and related antibiotics
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-
-
(2E,6E)-farnesyl diphosphate = pentalenene + diphosphate
stereochemistry
-
-
(2E,6E)-farnesyl diphosphate = pentalenene + diphosphate
mechanism
-
-
(2E,6E)-farnesyl diphosphate = pentalenene + diphosphate
stereochemistry, SE reaction type
-
-
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(2E,6E)-farnesyl diphosphate
pentalenene + diphosphate
2-trans,6-trans-farnesyl diphosphate
pentalenene + diphosphate
farnesyl diphosphate
pentalenene + diphosphate
additional information
?
-
isotopically sensitive branching experiments support a mechanism for pentalenene formation involving a 7-protoilludyl cation intermediate
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-
?
(2E,6E)-farnesyl diphosphate
pentalenene + diphosphate
-
-
-
-
?
(2E,6E)-farnesyl diphosphate
pentalenene + diphosphate
-
-
-
?
(2E,6E)-farnesyl diphosphate
pentalenene + diphosphate
-
-
-
-
?
(2E,6E)-farnesyl diphosphate
pentalenene + diphosphate
-
-
-
?
2-trans,6-trans-farnesyl diphosphate
pentalenene + diphosphate
the study describes theoretical studies on the cyclization reaction
-
-
?
2-trans,6-trans-farnesyl diphosphate
pentalenene + diphosphate
-
-
-
-
?
2-trans,6-trans-farnesyl diphosphate
pentalenene + diphosphate
-
-
-
-
?
farnesyl diphosphate
pentalenene + diphosphate
-
-
-
?
farnesyl diphosphate
pentalenene + diphosphate
-
mutant H309A produces 81% pentalenene and 13.4% Delta6-protoilludene, accompanied by minor quantities of germacrene A
-
?
farnesyl diphosphate
pentalenene + diphosphate
-
-
-
?
farnesyl diphosphate
pentalenene + diphosphate
-
-
-
?
farnesyl diphosphate
pentalenene + diphosphate
-
-
-
?
farnesyl diphosphate
pentalenene + diphosphate
-
-
-
?
farnesyl diphosphate
pentalenene + diphosphate
-
-
-
?
farnesyl diphosphate
pentalenene + diphosphate
-
the initial step in the reaction is probably a cyclization of farnesyl diphosphate to form humulene
-
?
farnesyl diphosphate
pentalenene + diphosphate
-
trans,trans
-
?
farnesyl diphosphate
pentalenene + diphosphate
-
trans,trans
-
?
farnesyl diphosphate
pentalenene + diphosphate
-
-
-
?
farnesyl diphosphate
pentalenene + diphosphate
-
-
-
?
farnesyl diphosphate
pentalenene + diphosphate
-
trans,trans
-
?
farnesyl diphosphate
pentalenene + diphosphate
-
-
-
?
farnesyl diphosphate
pentalenene + diphosphate
-
the initial step in the reaction is probably a cyclization of farnesyl diphosphate to form humulene
-
?
farnesyl diphosphate
pentalenene + diphosphate
-
-
-
?
farnesyl diphosphate
pentalenene + diphosphate
-
trans,trans
-
?
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(2E,6E)-farnesyl diphosphate
pentalenene + diphosphate
2-trans,6-trans-farnesyl diphosphate
pentalenene + diphosphate
the study describes theoretical studies on the cyclization reaction
-
-
?
farnesyl diphosphate
pentalenene + diphosphate
(2E,6E)-farnesyl diphosphate
pentalenene + diphosphate
-
-
-
-
?
(2E,6E)-farnesyl diphosphate
pentalenene + diphosphate
-
-
-
?
(2E,6E)-farnesyl diphosphate
pentalenene + diphosphate
-
-
-
-
?
(2E,6E)-farnesyl diphosphate
pentalenene + diphosphate
-
-
-
?
farnesyl diphosphate
pentalenene + diphosphate
-
-
-
?
farnesyl diphosphate
pentalenene + diphosphate
-
-
-
?
farnesyl diphosphate
pentalenene + diphosphate
-
-
-
?
farnesyl diphosphate
pentalenene + diphosphate
-
-
-
?
farnesyl diphosphate
pentalenene + diphosphate
-
-
-
?
farnesyl diphosphate
pentalenene + diphosphate
-
-
-
?
farnesyl diphosphate
pentalenene + diphosphate
-
-
-
?
farnesyl diphosphate
pentalenene + diphosphate
-
-
-
?
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0.00016 - 0.0166
(2E,6E)-farnesyl diphosphate
0.00077
(E,E)-farnesyl diphosphate
-
30°C, pH 8.4
0.0003 - 0.00031
farnesyl diphosphate
0.00016
(2E,6E)-farnesyl diphosphate
mutant enzyme W308F, pH and temperature not specified in the publication
0.00019
(2E,6E)-farnesyl diphosphate
mutant enzyme H309A, pH and temperature not specified in the publication
0.00025
(2E,6E)-farnesyl diphosphate
mutant enzyme H309S, pH and temperature not specified in the publication
0.0003
(2E,6E)-farnesyl diphosphate
mutant enzyme F77Y, pH and temperature not specified in the publication
0.00033
(2E,6E)-farnesyl diphosphate
mutant enzyme H309C, pH and temperature not specified in the publication
0.00143
(2E,6E)-farnesyl diphosphate
mutant enzyme H309F, pH and temperature not specified in the publication
0.00228
(2E,6E)-farnesyl diphosphate
mutant enzyme D84E, pH and temperature not specified in the publication
0.0026
(2E,6E)-farnesyl diphosphate
mutant enzyme D81E, pH and temperature not specified in the publication
0.00698
(2E,6E)-farnesyl diphosphate
mutant enzyme D80E, pH and temperature not specified in the publication
0.0166
(2E,6E)-farnesyl diphosphate
mutant enzyme N219D, pH and temperature not specified in the publication
0.0003
farnesyl diphosphate
30°C, pH 8.2
0.00031
farnesyl diphosphate
30°C, pH 8.2
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D80E
the mutation influences binding of the required divalent Mg2+ cofactor
D81E
the mutation influences binding of the required divalent Mg2+ cofactor
D84E
the mutation influences binding of the required divalent Mg2+ cofactor
N219A
catalytically inactive
W308F/H309F
reaction products are pentalene plus varying proportions of (+)-germacrene A
D84E
-
the mutation influences binding of the required divalent Mg2+ cofactor
-
H309A
-
the mutant exhibits nearly full wild type activity
-
H309C
-
the mutant exhibits nearly full wild type activity
-
H309F
-
the mutant exhibits nearly full wild type activity
-
H309S
-
the mutant exhibits nearly full wild type activity
-
F77Y
compared to wild type, kcat/Km value is 20fold lower
F77Y
the mutant exhibits nearly full wild type activity
H309A
retains enzymatic activity, minor increase in Km-value
H309A
the mutant exhibits nearly full wild type activity
H309C
retains enzymatic activity, minor increase in Km-value
H309C
the mutant exhibits nearly full wild type activity
H309F
retains enzymatic activity, minor increase in Km-value
H309F
reaction products are pentalene plus varying proportions of (+)-germacrene A and protoilludene
H309F
the mutant exhibits nearly full wild type activity
H309S
retains enzymatic activity, minor increase in Km-value
H309S
the mutant exhibits nearly full wild type activity
N219D
compared to wild type, kcat/Km value is 3300fold lower, reaction products are pentalene plus beta-caryophyllene
N219D
the mutation influences binding of the required divalent Mg2+ cofactor
N219L
catalytically inactive
N219L
the mutation influences binding of the required divalent Mg2+ cofactor
W308F
reaction products are pentalene plus varying proportions of (+)-germacrene A
W308F
the mutant exhibits nearly full wild type activity
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Cane, D.E.
Cell-free studies of monoterpene and sesquiterpene biosynthesis
Biochem. Soc. Trans.
11
510-515
1983
Streptomyces sp., Streptomyces sp. UC5319
brenda
Cane, D.E.; Pargellis, C.
Partial purification and characterization of pentalenene synthase
Arch. Biochem. Biophys.
254
421-429
1987
Streptomyces sp., Streptomyces sp. UC5319
brenda
Cane, D.E.; Oliver, J.S.; Harrison, P.H.M.; Abell, C.; Hubbard, B.R.; Kane, C.T.; Lattman, R.
The biosynthesis of pentalenene and pentalenolactone
J. Am. Chem. Soc.
112
4513-4524
1990
Streptomyces sp., Streptomyces sp. UC5319
-
brenda
Cane, D.E.; Abell, C.; Lattman, R.; Kane, C.T.; Hubbard, B.R.; Harrison, P.H.M.
Pentalenene biosynthesis and the enzymatic cyclisation of farnesyl pyrophosphate. Anti stereochemistry in a biological SE reaction
J. Am. Chem. Soc.
110
4081-4082
1988
Streptomyces sp., Streptomyces sp. UC5319
-
brenda
Cane, D.E.; Sohng, J.K.; Lamberson, C.R.; Rudnicki, S.M.; Wu, Z.; Lloyd, M.D.; Oliver, J.S.; Hubbard, B.R.
Pentalenene synthase. Purification, molecular cloning, sequencing, and high-level expression in Escherichia coli of a terpenoid cyclase from Streptomyces UC5319
Biochemistry
33
5846-5857
1994
Streptomyces exfoliatus (Q55012), Streptomyces exfoliatus UC5319 (Q55012)
brenda
Cane, D.E.; Weiner, S.W.
Cyclization of farnesyl diphosphate to pentalenene. Orthogonal stereochemistry in an enzyme-catalyzed SE' reaction
Can. J. Chem.
72
118-127
1994
Streptomyces sp., Streptomyces sp. UC5319
-
brenda
Lesburg, C.A.; Zhai, G.; Cane, D.E.; Christianson, D.W.
Crystal structure of pentalenene synthase: mechanistic insights on terpenoid cyclization reactions in biology
Science
277
1820-1824
1997
Streptomyces exfoliatus (Q55012), Streptomyces exfoliatus UC5319 (Q55012)
brenda
Seemann, M.; Zhai, G.; Umezawa, K.; Cane, D.
Pentalenene synthase. Histidine-309 is not required for catalytic activity
J. Am. Chem. Soc.
121
591-592
1999
Streptomyces exfoliatus (Q55012)
-
brenda
Seemann, M.; Zhai, G.; de Kraker, J.W.; Paschall, C.M.; Christianson, D.W.; Cane, D.E.
Pentalenene synthase. Analysis of active site residues by site-directed mutagenesis
J. Am. Chem. Soc.
124
7681-7689
2002
Streptomyces exfoliatus (Q55012)
brenda
Gutta, P.; Tantillo, D.J.
Theoretical studies on farnesyl cation cyclization: pathways to pentalenene
J. Am. Chem. Soc.
128
6172-6179
2006
Streptomyces exfoliatus (Q55012)
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Crystallization and preliminary X-ray diffraction analysis of recombinant pentalenene synthase
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4
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1995
Streptomyces exfoliatus (Q55012)
brenda
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134
11369-11371
2012
Streptomyces exfoliatus (Q55012)
brenda
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2012
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General base-general acid catalysis by terpenoid cyclases
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-
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