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Information on EC 2.3.1.47 - 8-amino-7-oxononanoate synthase
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EC Tree
2.3.1.47 8-amino-7-oxononanoate synthaseIUBMB Comments
A pyridoxal-phosphate protein. The enzyme catalyses the decarboxylative condensation of L-alanine and pimeloyl-[acyl-carrier protein], a key step in the pathway for biotin biosynthesis. Pimeloyl-CoA can be used with lower efficiency .
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Word Map
- 2.3.1.47
- biotin
- pimeloyl-coa
- dethiobiotin
-
plp-dependent
-
aldimine
- sphaericus
-
tympanometric
-
pyridoxal-5'-phosphate-dependent
-
alpha-oxoamine
-
2-amino-3-ketobutyrate
- agriculture
- medicine
- drug development
The enzyme appears in viruses and cellular organisms
Reaction Schemes
Synonyms
dapa at, 8-amino-7-oxononanoate synthase, 7,8-diaminopelargonic acid aminotransferase, 8-amino-7-oxopelargonate synthase, kapa synthase, kapas, biof protein, 7-keto-8-aminopelargonic acid synthase, 7-keto-8-aminopelargonic acid synthetase, atbiof, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
7,8-diaminopelargonic acid aminotransferase
7-keto-8-aminopelargonate synthase
7-keto-8-aminopelargonate synthetase
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-
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7-keto-8-aminopelargonic acid synthase
7-keto-8-aminopelargonic acid synthetase
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7-keto-8-aminopelargonic synthetase
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7-oxo-8-aminononanoate synthase
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8-amino-7-oxononanoate synthase
8-amino-7-oxopelargonate synthase
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AON synthase
AONS
BioF
bioF protein
DAPA AT
KAPA synthase
KAPA synthetase
SxtA
synthase, 7-oxo-8-aminononanoate
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synthetase, 7-keto-8-aminopelargonate
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additional information
additional information
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the enzyme is a member of the alpha-oxoamine synthase enzyme family
additional information
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the enzyme belongs to subclass II of the aminotransferase family
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
pimeloyl-[acyl-carrier protein] + L-alanine = 8-amino-7-oxononanoate + CO2 + holo-[acyl-carrier protein]
pimeloyl-[acyl-carrier protein] + L-alanine = 8-amino-7-oxononanoate + CO2 + holo-[acyl-carrier protein]
reaction mechanism
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pimeloyl-[acyl-carrier protein] + L-alanine = 8-amino-7-oxononanoate + CO2 + holo-[acyl-carrier protein]
reaction mechanism
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pimeloyl-[acyl-carrier protein] + L-alanine = 8-amino-7-oxononanoate + CO2 + holo-[acyl-carrier protein]
reaction mechanism
pimeloyl-[acyl-carrier protein] + L-alanine = 8-amino-7-oxononanoate + CO2 + holo-[acyl-carrier protein]
binding study of L-alanine and D-alanine to the enzyme
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pimeloyl-[acyl-carrier protein] + L-alanine = 8-amino-7-oxononanoate + CO2 + holo-[acyl-carrier protein]
binding study of L-alanine and D-alanine to the enzyme
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pimeloyl-[acyl-carrier protein] + L-alanine = 8-amino-7-oxononanoate + CO2 + holo-[acyl-carrier protein]
Schiff base formation between D- or L-alanine and pyridoxal-5'-phophate in the active site
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pimeloyl-[acyl-carrier protein] + L-alanine = 8-amino-7-oxononanoate + CO2 + holo-[acyl-carrier protein]
binding of pimeloyl-CoA causes a conformational change in the active site
-
pimeloyl-[acyl-carrier protein] + L-alanine = 8-amino-7-oxononanoate + CO2 + holo-[acyl-carrier protein]
reaction mechanism, formation of the pyridoxal-phosphate-stabilized carbanion by abstraction of the C2-H proton of the alanine-pyridoxal-phosphate aldimine, followed by acylation and decarboxylation
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pimeloyl-[acyl-carrier protein] + L-alanine = 8-amino-7-oxononanoate + CO2 + holo-[acyl-carrier protein]
reaction mechanism could be shared by all alpha-oxoamine synthases
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pimeloyl-[acyl-carrier protein] + L-alanine = 8-amino-7-oxononanoate + CO2 + holo-[acyl-carrier protein]
analysis of the reaction mechanism via an enzyme-bound intermediate beta-ketoacid pyridoxal-5'-phosphate aldimine, presence of multiple catalytic residues in the Escherichia coli enzyme
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pimeloyl-[acyl-carrier protein] + L-alanine = 8-amino-7-oxononanoate + CO2 + holo-[acyl-carrier protein]
detailed catalytic reaction mechanism, overview
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pimeloyl-[acyl-carrier protein] + L-alanine = 8-amino-7-oxononanoate + CO2 + holo-[acyl-carrier protein]
formation of an external intermediate beta-ketoacid pyridoxal-5'-phosphate aldimine, preference for L-alanine
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pimeloyl-[acyl-carrier protein] + L-alanine = 8-amino-7-oxononanoate + CO2 + holo-[acyl-carrier protein]
via an AtbioF-PLP internal aldimine complex, i.e. a Schiff base formed between PLP and a Lys residue in the protein
pimeloyl-[acyl-carrier protein] + L-alanine = 8-amino-7-oxononanoate + CO2 + holo-[acyl-carrier protein]
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
Acyl group transfer
-
-
-
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condensation
decarboxylation
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SYSTEMATIC NAME
IUBMB Comments
6-carboxyhexanoyl-[acyl-carrier protein]:L-alanine C-carboxyhexanoyltransferase (decarboxylating)
A pyridoxal-phosphate protein. The enzyme catalyses the decarboxylative condensation of L-alanine and pimeloyl-[acyl-carrier protein], a key step in the pathway for biotin biosynthesis. Pimeloyl-CoA can be used with lower efficiency [5].
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CAS REGISTRY NUMBER
COMMENTARY
9075-61-0
-
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
(R)-8-amino-7-oxononanoic acid + S-adenosyl-L-methionine
(7R,8S)-diaminopelargonic acid + S-adenosyl-(4-methylthio-2-oxobutanoic acid)
-
8.6% product is formed matching the portion of S-enantiomer substrate (9.3%),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, 1 mM S-adenosyl-L-methionine, 10 microM (R)-8-amino-7-oxononanoic acid
-
-
?
(S)-8-amino-7-oxononanoic acid + (R)-8-amino-7-oxononanoic acid + S-adenosyl-L-methionine
(7R,8S)-diaminopelargonic acid + S-adenosyl-(4-methylthio-2-oxobutanoic acid)
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46.3% product is formed from the racemic substrate, 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, 1 mM S-adenosyl-L-methionine, 2 microM racemic 8-amino-7-oxononanoic acid
-
-
?
(S)-8-amino-7-oxononanoic acid + S-adenosyl-L-methionine
(7R,8S)-diaminopelargonic acid + S-adenosyl-(4-methylthio-2-oxobutanoic acid)
6-carboxyhexanoyl-CoA + D-alanine
8-amino-7-oxononanoate + CoA + CO2
-
the L-isomer of the amino acid is preferred, D-alanine shows 5fold slower reaction, interaction analysis, overview
i.e. D-KAPA
-
?
6-carboxyhexanoyl-CoA + L-serine
9-hydroxy-8-amino-7-oxononanoate + CoA
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low activity
-
?
cyclopentanoyl-CoA + L-arginine
N-[(4S)-4-amino-5-cyclopentyl-5-oxopentyl]guanidine + CO2 + CoA
indole-3-carboxylic acid + 1-(2,6-dihydroxyphenyl)-butan-1-one
indolchromin A + CO2 + H2O
-
-
-
-
?
isobutanoyl-CoA + L-arginine
N-[(4S)-4-amino-6-methyl-5-oxoheptyl]guanidine + CO2 + CoA
-
-
-
-
?
isovaleryl-CoA + L-arginine
N-[(4S)-4-amino-7-methyl-5-oxooctyl]guanidine + CO2 + CoA
-
-
-
-
?
octanoyl-CoA + L-arginine
N-[(4S)-4-amino-5-oxododecyl]guanidine + CO2 + CoA
-
-
-
-
?
pimeloyl-CoA + L-alanine methyl ester
?
-
trapping and determination of the reaction intermediate using the the more stable methyl ester of the substrate, overview
-
-
?
pimeloyl-[acyl carrier protein] + L-alanine
8-amino-7-oxononanoate + CO2 + [acyl carrier protein]
-
-
-
?
pimeloyl-[acyl-carrier protein] + L-alanine
8-amino-7-oxononanoate + CO2 + holo-[acyl-carrier protein]
propionyl-CoA + L-arginine
N-[(4S)-4-amino-5-oxoheptyl]guanidine + CO2 + CoA
-
-
-
-
?
propionyl-[acyl-carrier protein] + L-alanine
1-[(4S)-4-amino-5-oxoheptyl]guanidine + CO2 + holo-[acyl-carrier protein]
-
-
-
-
?
propionyl-[acyl-carrier protein] + L-arginine
N-[(4S)-4-amino-5-oxoheptyl]guanidine + CO2 + holo-[acyl-carrier protein]
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-
-
-
?
(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
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-
?
(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
-
-
?
(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, 1 mM S-adenosyl-L-methionine, 2 microM (S)-8-amino-7-oxononanoic acid
-
-
?
(S)-8-amino-7-oxononanoic acid + S-adenosyl-L-methionine
(7R,8S)-diaminopelargonic acid + S-adenosyl-(4-methylthio-2-oxobutanoic acid)
-
93.2% product is formed matching the portion of S-enantiomer substrate (94.6%), 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, 1 mM S-adenosyl-L-methionine, 2 microM (S)-8-amino-7-oxononanoic 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
-
reaction in biotin biosynthesis
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
-
reaction in biotin biosynthesis
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
-
reaction in biotin biosynthesis
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
-
reaction in biotin biosynthesis
i.e. 7-oxo-8-amino-pelargonic acid
?
6-carboxyhexanoyl-CoA + L-alanine
8-amino-7-oxononanoate + CoA + CO2
Erwinia aroidea
-
i.e. pimeloyl-CoA
i.e. 7-oxo-8-amino-pelargonic acid
?
6-carboxyhexanoyl-CoA + L-alanine
8-amino-7-oxononanoate + CoA + CO2
Erwinia aroidea
-
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
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
-
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
reaction in biotin biosynthesis
i.e. 7-oxo-8-amino-pelargonic acid
?
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
-
-
?
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
-
i.e. pimeloyl-CoA
i.e. 7-oxo-8-amino-pelargonic acid
?
6-carboxyhexanoyl-CoA + L-alanine
8-amino-7-oxononanoate + CoA + CO2
-
L-cysteine cannot replace L-alanine
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
-
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
-
absolutely specific for L-alanine
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
?
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
-
i.e. pimeloyl-CoA
i.e. 7-oxo-8-amino-pelargonic acid
ir
6-carboxyhexanoyl-CoA + L-alanine
8-amino-7-oxononanoate + CoA + CO2
-
L-cysteine cannot replace L-alanine
i.e. 7-oxo-8-amino-pelargonic acid
?
6-carboxyhexanoyl-CoA + L-alanine
8-amino-7-oxononanoate + CoA + CO2
-
second step in biotin biosynthesis
i.e. 7-oxo-8-amino-pelargonic acid
ir
6-carboxyhexanoyl-CoA + L-alanine
8-amino-7-oxononanoate + CoA + CO2
-
second step 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
?
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
-
reaction in biotin biosynthesis
i.e. 7-oxo-8-amino-pelargonic acid
ir
6-carboxyhexanoyl-CoA + L-alanine
8-amino-7-oxononanoate + CoA + CO2
-
first committed step in the biotin biosynthesis pathway
-
-
?
6-carboxyhexanoyl-CoA + L-alanine
8-amino-7-oxononanoate + CoA + CO2
-
the L-isomer of the amino acid is preferred giving a 5fold faster reaction, interaction analysis, overview
i.e. L-KAPA
-
?
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
-
L-cysteine cannot replace L-alanine
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
-
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
Sporobolomyces coprophilus
-
i.e. pimeloyl-CoA
i.e. 7-oxo-8-amino-pelargonic acid
?
6-carboxyhexanoyl-CoA + L-alanine
8-amino-7-oxononanoate + CoA + CO2
Sporobolomyces coprophilus
-
reaction in biotin biosynthesis
i.e. 7-oxo-8-amino-pelargonic acid
?
acetyl-CoA + L-arginine
N-[(4S)-4-amino-5-oxohexyl]guanidine + CO2 + CoA
-
-
-
-
?
acetyl-CoA + L-arginine
N-[(4S)-4-amino-5-oxohexyl]guanidine + CO2 + CoA
-
-
-
-
?
benzoyl-CoA + L-arginine
N-[(4S)-4-amino-5-oxo-5-phenylpentyl]guanidine + CO2 + CoA
-
-
-
-
?
benzoyl-CoA + L-arginine
N-[(4S)-4-amino-5-oxo-5-phenylpentyl]guanidine + CO2 + CoA
-
-
-
-
?
butanoyl-CoA + L-arginine
N-[(4S)-4-amino-5-oxooctyl]guanidine + CO2 + CoA
-
-
-
-
?
butanoyl-CoA + L-arginine
N-[(4S)-4-amino-5-oxooctyl]guanidine + CO2 + CoA
-
-
-
-
?
cyclopentanoyl-CoA + L-arginine
N-[(4S)-4-amino-5-cyclopentyl-5-oxopentyl]guanidine + CO2 + CoA
-
-
-
-
?
cyclopentanoyl-CoA + L-arginine
N-[(4S)-4-amino-5-cyclopentyl-5-oxopentyl]guanidine + CO2 + CoA
-
-
-
-
?
hexanoyl-CoA + L-arginine
N-[(4S)-4-amino-5-oxodecyl]guanidine + CO2 + CoA
-
-
-
-
?
hexanoyl-CoA + L-arginine
N-[(4S)-4-amino-5-oxodecyl]guanidine + CO2 + CoA
-
-
-
-
?
L-alanine + pimeloyl-CoA
8-amino-7-oxononanoate + CoA + CO2
-
-
-
-
?
L-alanine + pimeloyl-CoA
8-amino-7-oxononanoate + CoA + CO2
-
-
-
-
?
L-alanine + pimeloyl-CoA
8-amino-7-oxononanoate + CoA + CO2
-
no activity observed with acetyl-CoA, no activity observed with glycine or L-serine
-
-
?
L-alanine + pimeloyl-CoA
8-amino-7-oxononanoate + CoA + CO2
-
-
-
-
?
L-alanine + pimeloyl-CoA
8-amino-7-oxononanoate + CoA + CO2
-
no activity observed with acetyl-CoA, no activity observed with glycine or L-serine
-
-
?
L-alanine + pimeloyl-CoA
8-amino-7-oxononanoate + CoA + CO2
-
no activity observed with acetyl-CoA, no activity observed with glycine or L-serine
-
-
?
L-alanine + pimeloyl-CoA
8-amino-7-oxononanoate + CoA + CO2
-
no activity observed with L-serine
-
-
?
L-alanine + pimeloyl-CoA
8-amino-7-oxononanoate + CoA + CO2
-
no activity observed with L-serine
-
-
?
L-alanine + pimeloyl-CoA
8-amino-7-oxononanoate + CoA + CO2
Thermosynechococcus vestitus
-
-
-
-
?
pimeloyl-CoA + L-alanine
8-amino-7-oxononanoate + CO2 + CoA
-
-
-
?
pimeloyl-CoA + L-alanine
8-amino-7-oxononanoate + CoA + CO2
-
-
-
?
pimeloyl-CoA + L-alanine
8-amino-7-oxononanoate + CoA + CO2
the enzyme is strictly stereospecific for L-alanine
-
-
?
pimeloyl-[acyl-carrier protein] + L-alanine
8-amino-7-oxononanoate + CO2 + holo-[acyl-carrier protein]
-
-
-
?
pimeloyl-[acyl-carrier protein] + L-alanine
8-amino-7-oxononanoate + CO2 + holo-[acyl-carrier protein]
-
-
-
?
pimeloyl-[acyl-carrier protein] + L-alanine
8-amino-7-oxononanoate + CO2 + holo-[acyl-carrier protein]
-
-
-
-
?
pimeloyl-[acyl-carrier protein] + L-alanine
8-amino-7-oxononanoate + CO2 + holo-[acyl-carrier protein]
-
-
-
?
additional information
?
-
the enzyme catalyzes the first committed enzyme of the biotin synthesis pathway
-
-
?
additional information
?
-
the enzyme is unable to utilize pimeloyl-[acyl carrier protein]
-
-
-
additional information
?
-
-
the enzyme is unable to utilize pimeloyl-[acyl carrier protein]
-
-
-
additional information
?
-
the enzyme is unable to utilize pimeloyl-[acyl carrier protein]
-
-
-
additional information
?
-
-
pimeloyl-CoA forms a quinonoid with L- or D-KAPA
-
-
?
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NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
(S)-8-amino-7-oxononanoic acid + S-adenosyl-L-methionine
(7R,8S)-diaminopelargonic acid + S-adenosyl-(4-methylthio-2-oxobutanoic acid)
pimeloyl-CoA + L-alanine
8-amino-7-oxononanoate + CoA + CO2
-
-
-
?
pimeloyl-[acyl-carrier protein] + L-alanine
8-amino-7-oxononanoate + CO2 + holo-[acyl-carrier protein]
additional information
?
-
the enzyme catalyzes the first committed enzyme of the biotin synthesis pathway
-
-
?
(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
-
-
?
(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
-
-
?
(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, 1 mM S-adenosyl-L-methionine, 2 microM (S)-8-amino-7-oxononanoic 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
-
reaction in biotin biosynthesis
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
-
reaction in biotin biosynthesis
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
-
reaction in biotin biosynthesis
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
-
reaction in biotin biosynthesis
i.e. 7-oxo-8-amino-pelargonic acid
?
6-carboxyhexanoyl-CoA + L-alanine
8-amino-7-oxononanoate + CoA + CO2
Erwinia aroidea
-
i.e. pimeloyl-CoA