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Synonyms
dapa at, 8-amino-7-oxononanoate synthase, 7,8-diaminopelargonic acid aminotransferase, 8-amino-7-oxopelargonate synthase, kapas, kapa synthase, 7-keto-8-aminopelargonic acid synthase, biof protein, atbiof, 7-keto-8-aminopelargonic acid synthetase,
more
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6-carboxyhexanoyl-CoA + L-alanine
8-amino-7-oxononanoate + CoA + CO2
L-alanine + pimeloyl-CoA
8-amino-7-oxononanoate + CoA + CO2
-
-
-
?
pimeloyl-CoA + L-alanine
8-amino-7-oxononanoate + CO2 + CoA
-
-
-
?
pimeloyl-[acyl carrier protein] + L-alanine
8-amino-7-oxononanoate + CO2 + [acyl carrier protein]
-
-
-
?
(S)-8-amino-7-oxononanoic acid + S-adenosyl-L-methionine
(7R,8S)-diaminopelargonic acid + S-adenosyl-(4-methylthio-2-oxobutanoic acid)
-
37°C, direct assay with 100 mM N-(2-hydroxyethyl)piperazine-N'-(2-propanesulfonic acid) buffer (pH 8.6), 0.1 mM pyridoxal 5'-phosphate, varying S-adenosyl-L-methionine, 9 microM (S)-8-amino-7-oxononanoic acid, varying inhibitor concentration
-
-
?
6-carboxyhexanoyl-CoA + L-alanine
8-amino-7-oxononanoate + CoA + CO2
6-carboxyhexanoyl-CoA + L-serine
9-hydroxy-8-amino-7-oxononanoate + CoA
-
low activity
-
?
L-alanine + pimeloyl-CoA
8-amino-7-oxononanoate + CoA + CO2
-
-
-
-
?
pimeloyl-CoA + L-alanine methyl ester
?
-
trapping and determination of the reaction intermediate using the the more stable methyl ester of the substrate, overview
-
-
?
6-carboxyhexanoyl-CoA + L-alanine
8-amino-7-oxononanoate + CoA + CO2
i.e. pimeloyl-CoA
i.e. 7-oxo-8-amino-pelargonic acid
?
6-carboxyhexanoyl-CoA + L-alanine
8-amino-7-oxononanoate + CoA + CO2
reaction in biotin biosynthesis
i.e. 7-oxo-8-amino-pelargonic acid
?
6-carboxyhexanoyl-CoA + L-alanine
8-amino-7-oxononanoate + CoA + CO2
-
-
-
-
?
6-carboxyhexanoyl-CoA + L-alanine
8-amino-7-oxononanoate + CoA + CO2
-
i.e. pimeloyl-CoA
i.e. 7-oxo-8-amino-pelargonic acid
?
6-carboxyhexanoyl-CoA + L-alanine
8-amino-7-oxononanoate + CoA + CO2
-
i.e. pimeloyl-CoA
i.e. 7-oxo-8-amino-pelargonic acid
?
6-carboxyhexanoyl-CoA + L-alanine
8-amino-7-oxononanoate + CoA + CO2
-
i.e. pimeloyl-CoA
i.e. 7-oxo-8-amino-pelargonic acid
?
6-carboxyhexanoyl-CoA + L-alanine
8-amino-7-oxononanoate + CoA + CO2
-
i.e. pimeloyl-CoA
i.e. 7-oxo-8-amino-pelargonic acid
ir
6-carboxyhexanoyl-CoA + L-alanine
8-amino-7-oxononanoate + CoA + CO2
-
i.e. pimeloyl-CoA
i.e. 7-oxo-8-amino-pelargonic acid
ir
6-carboxyhexanoyl-CoA + L-alanine
8-amino-7-oxononanoate + CoA + CO2
-
reaction in biotin biosynthesis
i.e. 7-oxo-8-amino-pelargonic acid
?
6-carboxyhexanoyl-CoA + L-alanine
8-amino-7-oxononanoate + CoA + CO2
-
reaction in biotin biosynthesis
i.e. 7-oxo-8-amino-pelargonic acid
?
6-carboxyhexanoyl-CoA + L-alanine
8-amino-7-oxononanoate + CoA + CO2
-
reaction in biotin biosynthesis
i.e. 7-oxo-8-amino-pelargonic acid
?
6-carboxyhexanoyl-CoA + L-alanine
8-amino-7-oxononanoate + CoA + CO2
-
reaction in biotin biosynthesis
i.e. 7-oxo-8-amino-pelargonic acid
ir
6-carboxyhexanoyl-CoA + L-alanine
8-amino-7-oxononanoate + CoA + CO2
-
reaction in biotin biosynthesis
i.e. 7-oxo-8-amino-pelargonic acid
ir
6-carboxyhexanoyl-CoA + L-alanine
8-amino-7-oxononanoate + CoA + CO2
-
the enzyme catalyzes the first committed step in the four step pathway, the decarboxylative condensation of L-alanine and pimeloyl-CoA to give (7S)-8-amino-7-oxononanoate
-
-
?
6-carboxyhexanoyl-CoA + L-alanine
8-amino-7-oxononanoate + CoA + CO2
-
a Claisen condensation
-
-
?
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6-carboxyhexanoyl-CoA + L-alanine
8-amino-7-oxononanoate + CoA + CO2
(S)-8-amino-7-oxononanoic acid + S-adenosyl-L-methionine
(7R,8S)-diaminopelargonic acid + S-adenosyl-(4-methylthio-2-oxobutanoic acid)
-
37°C, direct assay with 100 mM N-(2-hydroxyethyl)piperazine-N'-(2-propanesulfonic acid) buffer (pH 8.6), 0.1 mM pyridoxal 5'-phosphate, varying S-adenosyl-L-methionine, 9 microM (S)-8-amino-7-oxononanoic acid, varying inhibitor concentration
-
-
?
6-carboxyhexanoyl-CoA + L-alanine
8-amino-7-oxononanoate + CoA + CO2
6-carboxyhexanoyl-CoA + L-alanine
8-amino-7-oxononanoate + CoA + CO2
i.e. pimeloyl-CoA
i.e. 7-oxo-8-amino-pelargonic acid
?
6-carboxyhexanoyl-CoA + L-alanine
8-amino-7-oxononanoate + CoA + CO2
reaction in biotin biosynthesis
i.e. 7-oxo-8-amino-pelargonic acid
?
6-carboxyhexanoyl-CoA + L-alanine
8-amino-7-oxononanoate + CoA + CO2
-
-
-
-
?
6-carboxyhexanoyl-CoA + L-alanine
8-amino-7-oxononanoate + CoA + CO2
-
i.e. pimeloyl-CoA
i.e. 7-oxo-8-amino-pelargonic acid
?
6-carboxyhexanoyl-CoA + L-alanine
8-amino-7-oxononanoate + CoA + CO2
-
i.e. pimeloyl-CoA
i.e. 7-oxo-8-amino-pelargonic acid
?
6-carboxyhexanoyl-CoA + L-alanine
8-amino-7-oxononanoate + CoA + CO2
-
i.e. pimeloyl-CoA
i.e. 7-oxo-8-amino-pelargonic acid
?
6-carboxyhexanoyl-CoA + L-alanine
8-amino-7-oxononanoate + CoA + CO2
-
i.e. pimeloyl-CoA
i.e. 7-oxo-8-amino-pelargonic acid
ir
6-carboxyhexanoyl-CoA + L-alanine
8-amino-7-oxononanoate + CoA + CO2
-
i.e. pimeloyl-CoA
i.e. 7-oxo-8-amino-pelargonic acid
ir
6-carboxyhexanoyl-CoA + L-alanine
8-amino-7-oxononanoate + CoA + CO2
-
reaction in biotin biosynthesis
i.e. 7-oxo-8-amino-pelargonic acid
?
6-carboxyhexanoyl-CoA + L-alanine
8-amino-7-oxononanoate + CoA + CO2
-
reaction in biotin biosynthesis
i.e. 7-oxo-8-amino-pelargonic acid
?
6-carboxyhexanoyl-CoA + L-alanine
8-amino-7-oxononanoate + CoA + CO2
-
reaction in biotin biosynthesis
i.e. 7-oxo-8-amino-pelargonic acid
?
6-carboxyhexanoyl-CoA + L-alanine
8-amino-7-oxononanoate + CoA + CO2
-
reaction in biotin biosynthesis
i.e. 7-oxo-8-amino-pelargonic acid
ir
6-carboxyhexanoyl-CoA + L-alanine
8-amino-7-oxononanoate + CoA + CO2
-
reaction in biotin biosynthesis
i.e. 7-oxo-8-amino-pelargonic acid
ir
6-carboxyhexanoyl-CoA + L-alanine
8-amino-7-oxononanoate + CoA + CO2
-
the enzyme catalyzes the first committed step in the four step pathway, the decarboxylative condensation of L-alanine and pimeloyl-CoA to give (7S)-8-amino-7-oxononanoate
-
-
?
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0.0033 - 0.0153
(R)-8-amino-7-oxononanoic acid
0.0033
(R)-8-amino-7-oxononanoic acid
-
uncompetitive constant, pyridoxal 5'-phosphate form of enzyme, coupled assay at 37°C with 100 mM N-(2-hydroxyethyl)piperazine-N'-(2-propanesulfonic acid) buffer (pH 8.6), 10 mM ATP, 50 mM NaHCO3, 10 mM MgCl2, dithiobiotin syntetase, 0.1 mM pyridoxal 5'-phosphate, varicous concentrations of S-adenosyl-L-methionine and 9 microM (S)-8-amino-7-oxononanoic acid, 0.2-20 microM inhibitor
0.0153
(R)-8-amino-7-oxononanoic acid
-
competitive constant, pyridoxal 5'-phosphate form of enzyme, coupled assay at 37°C with 100 mM N-(2-hydroxyethyl)piperazine-N'-(2-propanesulfonic acid) buffer (pH 8.6), 10 mM ATP, 50 mM NaHCO3, 10 mM MgCl2, dithiobiotin syntetase, 0.1 mM pyridoxal 5'-phosphate, varicous concentrations of S-adenosyl-L-methionine and 9 microM (S)-8-amino-7-oxononanoic acid, 0.2-20 microM inhibitor
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Eidenberg, M.A.; Star, C.
Synthesis of 7-oxo-8-aminopelargonic acid, a biotin vitamer, in cell-free extracts of Escherichia coli biotin auxotrophs
J. Bacteriol.
96
1291-1297
1968
Escherichia coli
brenda
Otsuka, A.J.; Buoncristiani, M.R.; Howard, P.K.; Flamm, J.; Johnson, C.; Yamamoto, R.; Uchida, K.; Cook, C.; Ruppert, J.; Matsuzaki, J.
The Escherichia coli biotin biosynthetic enzyme sequences predicted from the nucleotide sequence of the bio operon
J. Biol. Chem.
263
19577-19585
1988
Escherichia coli
brenda
Izumi, Y.; Sato, K.; Tani, Y.; Ogata, K.
Distribution of 7-keto-8-aminopelargonic acid synthetase in bacteria and the control mechanism of the enzyme activity
Agric. Biol. Chem.
37
1335-1340
1973
Alcaligenes faecalis, Bacillus subtilis, Citrobacter freundii, Enterobacter cloacae, Erwinia aroidea, Escherichia coli, Klebsiella aerogenes, Kocuria rosea, Lysinibacillus sphaericus, Pseudomonas fluorescens
-
brenda
Webster, S.P.; Campopiano, D.J.; Alexeev, D.; Alexeeva, M.; Watt, R.M.; Sawyer, L.; Baxter, R.L.
Characterization of 8-amino-7-oxononanoate synthase: a bacterial PLP-dependent, acyl CoA condensing enzyme
Biochem. Soc. Trans.
26
S268
1998
Lysinibacillus sphaericus, Escherichia coli
brenda
Alexeev, D.; Alexeeva, M.; Baxter, R.L.; Campopiano, D.J.; Webster, S.P.; Sawyer, L.
The crystal structure of 8-amino-7-oxononanoate synthase: a bacterial PLP-dependent, acyl-CoA-condensing enzyme
J. Mol. Biol.
284
401-419
1998
Escherichia coli (P12998), Escherichia coli
brenda
Webster, S.P.; Alexeev, D.; Campopiano, D.J.; Watt, R.M.; Alexeeva, M.; Sawyer, L.; Baxter, R.L.
Mechanism of 8-amino-7-oxononanoate synthase: spectroscopic, kinetic, and crystallographic studies
Biochemistry
39
516-528
2000
Escherichia coli
brenda
Kerbarh, O.; Campopiano, D.J.; Baxter, R.L.
Mechanism of alpha-oxoamine synthases: identification of the intermediate Claisen product in the 8-amino-7-oxononanoate synthase reaction
Chem. Commun. (Camb. )
2006
60-62
2006
Escherichia coli
brenda
Alexeev, D.; Baxter, R.L.; Campopiano, D.J.; Kerbarh, O.; Sawyer, L.; Tomczyk, N.; Watt, R.; Webster, S.P.
Suicide inhibition of alpha-oxamine synthases: structures of the covalent adducts of 8-amino-7-oxononanoate synthase with trifluoroalanine
Org. Biomol. Chem.
4
1209-1212
2006
Escherichia coli
brenda
Mann, S.; Colliandre, L.; Labesse, G.; Ploux, O.
Inhibition of 7,8-diaminopelargonic acid aminotransferase from Mycobacterium tuberculosis by chiral and achiral anologs of its substrate: biological implications
Biochimie
91
826-834
2009
Escherichia coli, Escherichia coli C268, Mycobacterium tuberculosis
brenda
Turbeville, T.D.; Zhang, J.; Adams, W.C.; Hunter, G.A.; Ferreira, G.C.
Functional asymmetry for the active sites of linked 5-aminolevulinate synthase and 8-amino-7-oxononanoate synthase
Arch. Biochem. Biophys.
511
107-117
2011
Escherichia coli (P12998)
brenda
Kubota, T.; Izumi, Y.
Detection and characterization of a thermophilic biotin biosynthetic enzyme, 7-keto-8-aminopelargonic acid synthase, from various thermophiles
Biosci. Biotechnol. Biochem.
76
685-690
2012
Acetivibrio thermocellus, Acetivibrio thermocellus ATCC 27405, Aquifex aeolicus, Escherichia coli, Geobacillus kaustophilus, Geobacillus kaustophilus JCM 12893, Symbiobacterium thermophilum, Symbiobacterium thermophilum IAM14863, Thermosynechococcus vestitus
brenda
Manandhar, M.; Cronan, J.E.
A Canonical biotin synthesis enzyme, 8-amino-7-oxononanoate synthase (BioF), utilizes different acyl chain donors in Bacillus subtilis and Escherichia coli
Appl. Environ. Microbiol.
84
e02084-17
2018
Bacillus subtilis (P53556), Bacillus subtilis, Bacillus subtilis 168 (P53556), Escherichia coli (P12998), Escherichia coli
brenda