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5,6-dimethylbenzimidazole + beta-nicotinate D-ribonucleotide
nicotinate + N1-(5-phospho-alpha-D-ribosyl)-5,6-dimethylbenzimidazole
beta-nicotinate D-ribonucleotide + 5(6)-nitrobenzimidazole
nicotinate + N1-(5-phospho-alpha-D-ribosyl)-5(6)-nitrobenzimidazole
-
-
-
-
?
beta-nicotinate D-ribonucleotide + 5,6-dichlorobenzimidazole
nicotinate + N1-(5-phospho-alpha-D-ribosyl)-5,6-dichlorobenzimidazole
-
-
-
-
?
beta-nicotinate D-ribonucleotide + 5,6-dimethylbenzimidazole
nicotinate + alpha-ribazole 5'-phosphate
beta-nicotinate D-ribonucleotide + 5,6-dimethylbenzimidazole
nicotinate + N1-(5-phospho-alpha-D-ribosyl)-5,6-dimethylbenzimidazole
beta-nicotinate D-ribonucleotide + 5-hydroxybenzimidazole
nicotinate + N1-(5-phospho-alpha-D-ribosyl)-5-hydroxybenzimidazole
beta-nicotinate D-ribonucleotide + 5-methoxybenzimidazole
nicotinate + N1-(5-phospho-alpha-D-ribosyl)-5-methoxybenzimidazole
beta-nicotinate D-ribonucleotide + 5-methylbenzimidazole
nicotinate + N1-(5-phospho-alpha-D-ribosyl)-5-methylbenzimidazole
beta-nicotinate D-ribonucleotide + benzimidazole
nicotinate + N1-(5-phospho-alpha-D-ribosyl)-benzimidazole
NAD+ + 5,6-dimethylbenzimidazole
nicotinamide + alpha-5,6-dimethylbenzimidazole adenine dinucleotide
nicotinamide nucleoside + benzimidazole
?
-
-
-
-
ir
nicotinic acid mononucleotide + 4,5-dimethyl-1,2-phenylenediamine
nicotinate + ?
-
-
-
-
?
nicotinic acid mononucleotide + adenine
7-alpha-D-ribofuranosyladenine 5'-phosphate + nicotinate
nicotinic acid mononucleotide + adenine
nicotinate + ?
-
-
-
-
?
nicotinic acid mononucleotide + benzimidazole
1-alpha-D-ribofuranosylbenzimidazole 5'-phosphate + nicotinate
nicotinic acid mononucleotide + benzimidazole
1-alpha-D-ribofuranosylbenzimidazole 5'-phosphate + nicotinic acid
-
-
alpha-ribazole 5'-phosphate, intermediate for the lower ligand of cobalamin
?
nicotinic acid mononucleotide + benzimidazole
nicotinate + N1-(5-phospho-alpha-D-ribosyl)-benzimidazole
-
-
-
-
?
nicotinic acid mononucleotide + guanine
nicotinate + ?
-
-
-
-
?
nicotinic acid mononucleotide + histidine
nicotinate + ?
-
-
-
-
?
nicotinic acid mononucleotide + imidazole
nicotinate + ?
-
-
-
-
?
nicotinic acid nucleoside + benzimidazole
?
-
-
-
-
ir
NMN + 5,6-dimethylbenzimidazole
nicotinamide + ?
-
-
-
-
?
NMN + benzimidazole
?
-
-
-
-
ir
p-cresol + beta-nicotinate D-ribonucleotide
nicotinate + 4-hydroxyphenyl alpha-D-ribose 5-phosphate
phenol + beta-nicotinate D-ribonucleotide
nicotinate + phenyl alpha-D-ribose 5-phosphate
additional information
?
-
5,6-dimethylbenzimidazole + beta-nicotinate D-ribonucleotide
nicotinate + N1-(5-phospho-alpha-D-ribosyl)-5,6-dimethylbenzimidazole
-
-
-
?
5,6-dimethylbenzimidazole + beta-nicotinate D-ribonucleotide
nicotinate + N1-(5-phospho-alpha-D-ribosyl)-5,6-dimethylbenzimidazole
-
-
-
-
?
beta-nicotinate D-ribonucleotide + 5,6-dimethylbenzimidazole
nicotinate + alpha-ribazole 5'-phosphate
-
-
-
-
?
beta-nicotinate D-ribonucleotide + 5,6-dimethylbenzimidazole
nicotinate + alpha-ribazole 5'-phosphate
-
-
-
?
beta-nicotinate D-ribonucleotide + 5,6-dimethylbenzimidazole
nicotinate + alpha-ribazole 5'-phosphate
-
-
-
?
beta-nicotinate D-ribonucleotide + 5,6-dimethylbenzimidazole
nicotinate + alpha-ribazole 5'-phosphate
-
-
-
-
?
beta-nicotinate D-ribonucleotide + 5,6-dimethylbenzimidazole
nicotinate + alpha-ribazole 5'-phosphate
-
-
-
-
?
beta-nicotinate D-ribonucleotide + 5,6-dimethylbenzimidazole
nicotinate + alpha-ribazole 5'-phosphate
-
-
-
-
?
beta-nicotinate D-ribonucleotide + 5,6-dimethylbenzimidazole
nicotinate + N1-(5-phospho-alpha-D-ribosyl)-5,6-dimethylbenzimidazole
-
-
-
-
?
beta-nicotinate D-ribonucleotide + 5,6-dimethylbenzimidazole
nicotinate + N1-(5-phospho-alpha-D-ribosyl)-5,6-dimethylbenzimidazole
-
-
-
ir
beta-nicotinate D-ribonucleotide + 5,6-dimethylbenzimidazole
nicotinate + N1-(5-phospho-alpha-D-ribosyl)-5,6-dimethylbenzimidazole
-
-
-
?
beta-nicotinate D-ribonucleotide + 5,6-dimethylbenzimidazole
nicotinate + N1-(5-phospho-alpha-D-ribosyl)-5,6-dimethylbenzimidazole
-
-
-
?
beta-nicotinate D-ribonucleotide + 5,6-dimethylbenzimidazole
nicotinate + N1-(5-phospho-alpha-D-ribosyl)-5,6-dimethylbenzimidazole
-
-
-
?
beta-nicotinate D-ribonucleotide + 5,6-dimethylbenzimidazole
nicotinate + N1-(5-phospho-alpha-D-ribosyl)-5,6-dimethylbenzimidazole
-
-
-
-
?
beta-nicotinate D-ribonucleotide + 5-hydroxybenzimidazole
nicotinate + N1-(5-phospho-alpha-D-ribosyl)-5-hydroxybenzimidazole
-
-
-
-
?
beta-nicotinate D-ribonucleotide + 5-hydroxybenzimidazole
nicotinate + N1-(5-phospho-alpha-D-ribosyl)-5-hydroxybenzimidazole
-
-
-
-
?
beta-nicotinate D-ribonucleotide + 5-hydroxybenzimidazole
nicotinate + N1-(5-phospho-alpha-D-ribosyl)-5-hydroxybenzimidazole
-
-
-
-
?
beta-nicotinate D-ribonucleotide + 5-methoxybenzimidazole
nicotinate + N1-(5-phospho-alpha-D-ribosyl)-5-methoxybenzimidazole
-
-
-
-
?
beta-nicotinate D-ribonucleotide + 5-methoxybenzimidazole
nicotinate + N1-(5-phospho-alpha-D-ribosyl)-5-methoxybenzimidazole
-
-
-
-
?
beta-nicotinate D-ribonucleotide + 5-methoxybenzimidazole
nicotinate + N1-(5-phospho-alpha-D-ribosyl)-5-methoxybenzimidazole
-
-
-
-
?
beta-nicotinate D-ribonucleotide + 5-methylbenzimidazole
nicotinate + N1-(5-phospho-alpha-D-ribosyl)-5-methylbenzimidazole
-
-
-
-
?
beta-nicotinate D-ribonucleotide + 5-methylbenzimidazole
nicotinate + N1-(5-phospho-alpha-D-ribosyl)-5-methylbenzimidazole
-
-
-
-
?
beta-nicotinate D-ribonucleotide + 5-methylbenzimidazole
nicotinate + N1-(5-phospho-alpha-D-ribosyl)-5-methylbenzimidazole
-
-
-
-
?
beta-nicotinate D-ribonucleotide + benzimidazole
nicotinate + N1-(5-phospho-alpha-D-ribosyl)-benzimidazole
-
-
-
-
?
beta-nicotinate D-ribonucleotide + benzimidazole
nicotinate + N1-(5-phospho-alpha-D-ribosyl)-benzimidazole
-
-
-
-
?
beta-nicotinate D-ribonucleotide + benzimidazole
nicotinate + N1-(5-phospho-alpha-D-ribosyl)-benzimidazole
-
-
-
-
?
NAD+ + 5,6-dimethylbenzimidazole
nicotinamide + alpha-5,6-dimethylbenzimidazole adenine dinucleotide
-
-
alpha-5,6-dimethylbenzimidazole adenine dinucleotide product identification by mass spectrometry
-
?
NAD+ + 5,6-dimethylbenzimidazole
nicotinamide + alpha-5,6-dimethylbenzimidazole adenine dinucleotide
-
step in the biosynthesis of coenzyme B12, nuceotide loop assembly NLA pathway overview
-
-
?
nicotinic acid mononucleotide + adenine
7-alpha-D-ribofuranosyladenine 5'-phosphate + nicotinate
-
-
-
?
nicotinic acid mononucleotide + adenine
7-alpha-D-ribofuranosyladenine 5'-phosphate + nicotinate
-
-
-
?
nicotinic acid mononucleotide + benzimidazole
1-alpha-D-ribofuranosylbenzimidazole 5'-phosphate + nicotinate
-
highly specific for nicotinic acid mononucleotide
-
?
nicotinic acid mononucleotide + benzimidazole
1-alpha-D-ribofuranosylbenzimidazole 5'-phosphate + nicotinate
-
best substrate
-
ir
nicotinic acid mononucleotide + benzimidazole
1-alpha-D-ribofuranosylbenzimidazole 5'-phosphate + nicotinate
-
alpha-ribazole 5'-phosphate
?
nicotinic acid mononucleotide + benzimidazole
1-alpha-D-ribofuranosylbenzimidazole 5'-phosphate + nicotinate
-
-
-
-
?
nicotinic acid mononucleotide + benzimidazole
1-alpha-D-ribofuranosylbenzimidazole 5'-phosphate + nicotinate
-
-
-
-
?
p-cresol + beta-nicotinate D-ribonucleotide
nicotinate + 4-hydroxyphenyl alpha-D-ribose 5-phosphate
-
-
-
?
p-cresol + beta-nicotinate D-ribonucleotide
nicotinate + 4-hydroxyphenyl alpha-D-ribose 5-phosphate
-
-
-
-
?
phenol + beta-nicotinate D-ribonucleotide
nicotinate + phenyl alpha-D-ribose 5-phosphate
-
-
-
?
phenol + beta-nicotinate D-ribonucleotide
nicotinate + phenyl alpha-D-ribose 5-phosphate
-
-
-
-
?
additional information
?
-
-
not substrate: NAD, ribose 1-phosphate, ribose 5-phosphate, 2-methylbenzimidazole
-
-
?
additional information
?
-
-
no activity with adenine, phenol, and p-cresol
-
-
?
additional information
?
-
-
substrate specificity
-
-
?
additional information
?
-
-
no activity with adenine, phenol, and p-cresol
-
-
?
additional information
?
-
phloroglucinol is identified from an additive screen as a compound that dramatically improves the size, stability, and diffraction properties of the crystals. Subsequent structural studies show that phloroglucinol binds in the active site of ArsA
-
-
?
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C160A
loss of catalytic efficiency by 79%. Renders the enzyme 5fold less efficient than wild-type. Displays no discernible growth defect in no-carbon essential (NCE) medium containing dicyanocobinamide and glycerol or ethanolamine relative to that of a strain that synthesizes wild-type
G171D
loss of catalytic efficiency by more than 99%, has less affinity for 5,6-dimethylbenzimidazole. Retains activity to support growth, but only when 5,6-dimethylbenzimidazole is present in the medium. Does not support the growth of strain JE2423 on ethanolamine in medium that contains dicyanocobinamide but lacks 5,6-dimethylbenzimidazole
G171D/M325A
requires cobalamin for growth regardless of the carbon source used
G257A
loss of catalytic efficiency by 64%
G257D
loss of catalytic efficiency by more than 99%, has less affinity for 5,6-dimethylbenzimidazole. Does not respond to 5,6-dimethylbenzimidazole and requires cobalamin to grow. Does not support the growth of strain JE2423 on ethanolamine in medium that contains dicyanocobinamide but lacks 5,6-dimethylbenzimidazole
G257D/P12G
is cobalamin auxotroph on glycerol or ethanolamine. P12G does not alter the effect of the G257D mutation
G320D
loss of catalytic efficiency by more than 99%, is unstable, retains activity to support growth, but only when 5,6-dimethylbenzimidazole is present in the medium. Does not support the growth of strain JE2423 on ethanolamine in medium that contains dicyanocobinamide but lacks 5,6-dimethylbenzimidazole
H289A
counteracts the effect of the G320D substitution
M325A
grows in the absence of exogenous 5,6-dimethylbenzimidazole, albeit at a rate slower than that of a strain making wild-type. Addition of 5,6-dimethylbenzimidazole to the medium allows the strain making M325A to grow as fast as a strain making wild-type
P12G
does not require exogenous 5,6-dimethylbenzimidazole for growth on glycerol or ethanolamine
I321S
specific activity with p-cresol and 5,6-dimethylbenzimidazole decreased
M87Q
effect of the M87Q mutation is most pronounced with respect to phenolic specificity, as the specific activity with p-cresol drops by 2.6fold while a 1.2fold increase in activity with 5,6-dimethylbenzimidazole is observed
M87Q/I321S
specific activity with p-cresol and 5,6-dimethylbenzimidazole highly decreased
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Friedmann, H.C.
Partial purification and properties of a single displacement trans-N-glycoside
J. Biol. Chem.
240
413-418
1965
Propionibacterium freudenreichii subsp. shermanii
brenda
Fyfe, J.A.; Friedmann, H.C.
Vitamin B 12 biosynthesis. Enzyme studies on the formation of the alpha-glycosidic nucleotide precursor
J. Biol. Chem.
244
1659-1666
1969
Acetoanaerobium sticklandii
brenda
Friedmann, H.C.; Fyfe, J.A.
Pseudovitamin B 12 biosynthesis. Enzymatic formation of a new adenylic acid, 7-alpha-D-ribofuranosyladenine 5-phosphate
J. Biol. Chem.
244
1667-1671
1969
Acetoanaerobium sticklandii
brenda
Cameron, B.; Blanche, F.; Rouyez, M.C.; Bisch, D.; Famechon, A.; Couder, M.; Cauchois, L.; Thibaut, D.; Debussche, L.; Crouzet, J.
Genetic analysis, nucleotide sequence, and products of two Pseudomonas denitrificans cob genes encoding nicotinate-nucleotide: dimethylbenzimidazole phosphoribosyltransferase and cobalamin (5-phosphate) synthase
J. Bacteriol.
173
6066-6073
1991
Pseudomonas denitrificans (nom. rej.) (P29935), Pseudomonas denitrificans (nom. rej.)
brenda
Trzebiatowski, J.R.; Escalante-Semerena, J.C.
Purification and characterization of CobT, the nicotinate-mononucleotide:5,6-dimethylbenzimidazole phosphoribosyltransferase enzyme from Salmonella typhimurium LT2
J. Biol. Chem.
272
17662-17667
1997
Salmonella enterica subsp. enterica serovar Typhimurium
brenda
Cheong, C.G.; Escalante-Semerena, J.C.; Rayment, I.
Capture of a labile substrate by expulsion of water molecules from the active site of nicotinate mononucleotide:5,6-dimethylbenzimidazole phosphoribosyltransferase (CobT) from Salmonella enterica
J. Biol. Chem.
277
41120-41127
2002
Salmonella enterica
brenda
Cheong, C.G.; Escalante-Semerena, J.C.; Rayment, I.
Structural investigation of the biosynthesis of alternative lower ligands for cobamides by nicotinate mononucleotide: 5,6-dimethylbenzimidazole phosphoribosyltransferase from Salmonella enterica
J. Biol. Chem.
276
37612-37620
2001
Salmonella enterica
brenda
Cheong, C.G.; Escalante-Semerena, J.C.; Rayment, I.
The three-dimensional structures of nicotinate mononucleotide:5,6-dimethylbenzimidazole phosphoribosyltransferase (CobT) from Salmonella typhimurium complexed with 5,6-dimethylbenzimidazole and its reaction products determined to 1.9.ANG. resolution
Biochemistry
38
16125-16135
1999
Salmonella enterica subsp. enterica serovar Typhimurium
brenda
Trzebiatowski, J.R.; O'Toole, G.A.; Escalante-Semerena, J.C.
The cobT gene of Salmonella typhimurium encodes the NaMN:5,6-dimethylbenzimidazole phosphoribosyltransferase responsible for the synthesis of N1-(5-phospho-a-D-ribosyl)-5,6-dimethylbenzimidazole, an intermediate in the synthesis of the nucleotide loop of cobalamin
J. Bacteriol.
176
3568-3575
1994
Salmonella enterica subsp. enterica serovar Typhimurium
brenda
Maggio-Hall, L.A.; Escalante-Semerena, J.C.
alpha-5,6-Dimethylbenzimidazole adenine dinucleotide (alpha-DAD), a putative new intermediate of coenzyme B12 biosynthesis in Salmonella typhimurium
Microbiology
149
983-990
2003
Salmonella enterica subsp. enterica serovar Typhimurium
brenda
Claas, K.R.; Parrish, J.R.; Maggio-Hall, L.A.; Escalante-Semerena, J.C.
Functional analysis of the nicotinate mononucleotide:5,6-dimethylbenzimidazole phosphoribosyltransferase (CobT) enzyme, involved in the late steps of coenzyme B12 biosynthesis in Salmonella enterica
J. Bacteriol.
192
145-154
2010
Salmonella enterica (Q05603)
brenda
Newmister, S.A.; Chan, C.H.; Escalante-Semerena, J.C.; Rayment, I.
Structural Insights into the Function of the Nicotinate Mononucleotide:phenol/p-cresol Phosphoribosyltransferase (ArsAB) Enzyme from Sporomusa ovata
Biochemistry
51
8571-8582
2012
Sporomusa ovata (F6MZ55 and F6MZ56)
brenda
Chan, C.H.; Escalante-Semerena, J.C.
ArsAB, a novel enzyme from Sporomusa ovata activates phenolic bases for adenosylcobamide biosynthesis
Mol. Microbiol.
81
952-967
2011
Sporomusa ovata (F6MZ55 and F6MZ56), Sporomusa ovata
brenda
Crofts, T.S.; Hazra, A.B.; Tran, J.L.; Sokolovskaya, O.M.; Osadchiy, V.; Ad, O.; Pelton, J.; Bauer, S.; Taga, M.E.
Regiospecific formation of cobamide isomers is directed by CobT
Biochemistry
53
7805-7815
2014
Salmonella enterica, Sinorhizobium meliloti, Salmonella enterica LT2
brenda
Crofts, T.S.; Seth, E.C.; Hazra, A.B.; Taga, M.E.
Cobamide structure depends on both lower ligand availability and CobT substrate specificity
Chem. Biol.
20
1265-1274
2013
Salmonella enterica, Sinorhizobium meliloti
brenda
Deptula, P.; Kylli, P.; Chamlagain, B.; Holm, L.; Kostiainen, R.; Piironen, V.; Savijoki, K.; Varmanen, P.
BluB/CobT2 fusion enzyme activity reveals mechanisms responsible for production of active form of vitamin B12 by Propionibacterium freudenreichii
Microb. Cell Fact.
14
186
2015
Propionibacterium freudenreichii (D7GJ95), Propionibacterium freudenreichii DSM 4902 (D7GJ95)
brenda
Mattes, T.; Escalante-Semerena, J.
Salmonella enterica synthesizes 5,6-dimethylbenzimidazolyl-(DMB)-alpha-riboside. Why some Firmicutes do not require the canonical DMB activation system to synthesize adenosylcobalamin
Mol. Microbiol.
103
269-281
2017
Salmonella enterica, Geobacillus kaustophilus
brenda