2.3.1.47 (R)-8-amino-7-oxononanoic acid + S-adenosyl-L-methionine 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 Mycobacterium tuberculosis (7R,8S)-diaminopelargonic acid + S-adenosyl-(4-methylthio-2-oxobutanoic acid) - ? 407647 2.3.1.47 (S)-8-amino-7-oxononanoic acid + (R)-8-amino-7-oxononanoic acid + S-adenosyl-L-methionine 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 Mycobacterium tuberculosis (7R,8S)-diaminopelargonic acid + S-adenosyl-(4-methylthio-2-oxobutanoic acid) - ? 407677 2.3.1.47 (S)-8-amino-7-oxononanoic acid + S-adenosyl-L-methionine 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 Mycobacterium tuberculosis (7R,8S)-diaminopelargonic acid + S-adenosyl-(4-methylthio-2-oxobutanoic acid) - ? 406980 2.3.1.47 (S)-8-amino-7-oxononanoic acid + S-adenosyl-L-methionine 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 Escherichia coli (7R,8S)-diaminopelargonic acid + S-adenosyl-(4-methylthio-2-oxobutanoic acid) - ? 406980 2.3.1.47 (S)-8-amino-7-oxononanoic acid + S-adenosyl-L-methionine 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 Mycobacterium tuberculosis (7R,8S)-diaminopelargonic acid + S-adenosyl-(4-methylthio-2-oxobutanoic acid) - ? 406980 2.3.1.47 (S)-8-amino-7-oxononanoic acid + S-adenosyl-L-methionine 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 Escherichia coli C268 (7R,8S)-diaminopelargonic acid + S-adenosyl-(4-methylthio-2-oxobutanoic acid) - ? 406980 2.3.1.47 6-carboxyhexanoyl-CoA + D-alanine the L-isomer of the amino acid is preferred, D-alanine shows 5fold slower reaction, interaction analysis, overview Mycobacterium tuberculosis 8-amino-7-oxononanoate + CoA + CO2 i.e. D-KAPA ? 387629 2.3.1.47 6-carboxyhexanoyl-CoA + L-alanine - Escherichia coli 8-amino-7-oxononanoate + CoA + CO2 - ? 320929 2.3.1.47 6-carboxyhexanoyl-CoA + L-alanine absolutely specific for L-alanine Lysinibacillus sphaericus 8-amino-7-oxononanoate + CoA + CO2 i.e. 7-oxo-8-amino-pelargonic acid ? 320929 2.3.1.47 6-carboxyhexanoyl-CoA + L-alanine i.e. pimeloyl-CoA Alcaligenes faecalis 8-amino-7-oxononanoate + CoA + CO2 i.e. 7-oxo-8-amino-pelargonic acid ? 320929 2.3.1.47 6-carboxyhexanoyl-CoA + L-alanine i.e. pimeloyl-CoA Bacillus subtilis 8-amino-7-oxononanoate + CoA + CO2 i.e. 7-oxo-8-amino-pelargonic acid ? 320929 2.3.1.47 6-carboxyhexanoyl-CoA + L-alanine i.e. pimeloyl-CoA Escherichia coli 8-amino-7-oxononanoate + CoA + CO2 i.e. 7-oxo-8-amino-pelargonic acid ? 320929 2.3.1.47 6-carboxyhexanoyl-CoA + L-alanine i.e. pimeloyl-CoA Escherichia coli 8-amino-7-oxononanoate + CoA + CO2 i.e. 7-oxo-8-amino-pelargonic acid ir 320929 2.3.1.47 6-carboxyhexanoyl-CoA + L-alanine i.e. pimeloyl-CoA Enterobacter cloacae 8-amino-7-oxononanoate + CoA + CO2 i.e. 7-oxo-8-amino-pelargonic acid ? 320929 2.3.1.47 6-carboxyhexanoyl-CoA + L-alanine i.e. pimeloyl-CoA Lysinibacillus sphaericus 8-amino-7-oxononanoate + CoA + CO2 i.e. 7-oxo-8-amino-pelargonic acid ? 320929 2.3.1.47 6-carboxyhexanoyl-CoA + L-alanine i.e. pimeloyl-CoA Lysinibacillus sphaericus 8-amino-7-oxononanoate + CoA + CO2 i.e. 7-oxo-8-amino-pelargonic acid ir 320929 2.3.1.47 6-carboxyhexanoyl-CoA + L-alanine i.e. pimeloyl-CoA Kocuria rosea 8-amino-7-oxononanoate + CoA + CO2 i.e. 7-oxo-8-amino-pelargonic acid ? 320929 2.3.1.47 6-carboxyhexanoyl-CoA + L-alanine i.e. pimeloyl-CoA Pseudomonas fluorescens 8-amino-7-oxononanoate + CoA + CO2 i.e. 7-oxo-8-amino-pelargonic acid ? 320929 2.3.1.47 6-carboxyhexanoyl-CoA + L-alanine i.e. pimeloyl-CoA Klebsiella aerogenes 8-amino-7-oxononanoate + CoA + CO2 i.e. 7-oxo-8-amino-pelargonic acid ? 320929 2.3.1.47 6-carboxyhexanoyl-CoA + L-alanine i.e. pimeloyl-CoA Lipomyces starkeyi 8-amino-7-oxononanoate + CoA + CO2 i.e. 7-oxo-8-amino-pelargonic acid ? 320929 2.3.1.47 6-carboxyhexanoyl-CoA + L-alanine i.e. pimeloyl-CoA Sporidiobolus salmonicolor 8-amino-7-oxononanoate + CoA + CO2 i.e. 7-oxo-8-amino-pelargonic acid ? 320929 2.3.1.47 6-carboxyhexanoyl-CoA + L-alanine i.e. pimeloyl-CoA Sporobolomyces coprophilus 8-amino-7-oxononanoate + CoA + CO2 i.e. 7-oxo-8-amino-pelargonic acid ? 320929 2.3.1.47 6-carboxyhexanoyl-CoA + L-alanine i.e. pimeloyl-CoA Citrobacter freundii 8-amino-7-oxononanoate + CoA + CO2 i.e. 7-oxo-8-amino-pelargonic acid ? 320929 2.3.1.47 6-carboxyhexanoyl-CoA + L-alanine i.e. pimeloyl-CoA Erwinia aroidea 8-amino-7-oxononanoate + CoA + CO2 i.e. 7-oxo-8-amino-pelargonic acid ? 320929 2.3.1.47 6-carboxyhexanoyl-CoA + L-alanine L-cysteine cannot replace L-alanine Lysinibacillus sphaericus 8-amino-7-oxononanoate + CoA + CO2 i.e. 7-oxo-8-amino-pelargonic acid ? 320929 2.3.1.47 6-carboxyhexanoyl-CoA + L-alanine L-cysteine cannot replace L-alanine Kocuria rosea 8-amino-7-oxononanoate + CoA + CO2 i.e. 7-oxo-8-amino-pelargonic acid ? 320929 2.3.1.47 6-carboxyhexanoyl-CoA + L-alanine L-cysteine cannot replace L-alanine Pseudomonas fluorescens 8-amino-7-oxononanoate + CoA + CO2 i.e. 7-oxo-8-amino-pelargonic acid ? 320929 2.3.1.47 6-carboxyhexanoyl-CoA + L-alanine second step in biotin biosynthesis Lysinibacillus sphaericus 8-amino-7-oxononanoate + CoA + CO2 i.e. 7-oxo-8-amino-pelargonic acid ir 320929 2.3.1.47 6-carboxyhexanoyl-CoA + L-alanine reaction in biotin biosynthesis Alcaligenes faecalis 8-amino-7-oxononanoate + CoA + CO2 i.e. 7-oxo-8-amino-pelargonic acid ? 320929 2.3.1.47 6-carboxyhexanoyl-CoA + L-alanine reaction in biotin biosynthesis Bacillus subtilis 8-amino-7-oxononanoate + CoA + CO2 i.e. 7-oxo-8-amino-pelargonic acid ? 320929 2.3.1.47 6-carboxyhexanoyl-CoA + L-alanine reaction in biotin biosynthesis Escherichia coli 8-amino-7-oxononanoate + CoA + CO2 i.e. 7-oxo-8-amino-pelargonic acid ? 320929 2.3.1.47 6-carboxyhexanoyl-CoA + L-alanine reaction in biotin biosynthesis Escherichia coli 8-amino-7-oxononanoate + CoA + CO2 i.e. 7-oxo-8-amino-pelargonic acid ir 320929 2.3.1.47 6-carboxyhexanoyl-CoA + L-alanine reaction in biotin biosynthesis Enterobacter cloacae 8-amino-7-oxononanoate + CoA + CO2 i.e. 7-oxo-8-amino-pelargonic acid ? 320929 2.3.1.47 6-carboxyhexanoyl-CoA + L-alanine reaction in biotin biosynthesis Lysinibacillus sphaericus 8-amino-7-oxononanoate + CoA + CO2 i.e. 7-oxo-8-amino-pelargonic acid ? 320929 2.3.1.47 6-carboxyhexanoyl-CoA + L-alanine reaction in biotin biosynthesis Lysinibacillus sphaericus 8-amino-7-oxononanoate + CoA + CO2 i.e. 7-oxo-8-amino-pelargonic acid ir 320929 2.3.1.47 6-carboxyhexanoyl-CoA + L-alanine reaction in biotin biosynthesis Kocuria rosea 8-amino-7-oxononanoate + CoA + CO2 i.e. 7-oxo-8-amino-pelargonic acid ? 320929 2.3.1.47 6-carboxyhexanoyl-CoA + L-alanine reaction in biotin biosynthesis Pseudomonas fluorescens 8-amino-7-oxononanoate + CoA + CO2 i.e. 7-oxo-8-amino-pelargonic acid ? 320929 2.3.1.47 6-carboxyhexanoyl-CoA + L-alanine reaction in biotin biosynthesis Klebsiella aerogenes 8-amino-7-oxononanoate + CoA + CO2 i.e. 7-oxo-8-amino-pelargonic acid ? 320929 2.3.1.47 6-carboxyhexanoyl-CoA + L-alanine reaction in biotin biosynthesis Lipomyces starkeyi 8-amino-7-oxononanoate + CoA + CO2 i.e. 7-oxo-8-amino-pelargonic acid ? 320929 2.3.1.47 6-carboxyhexanoyl-CoA + L-alanine reaction in biotin biosynthesis Sporidiobolus salmonicolor 8-amino-7-oxononanoate + CoA + CO2 i.e. 7-oxo-8-amino-pelargonic acid ? 320929 2.3.1.47 6-carboxyhexanoyl-CoA + L-alanine reaction in biotin biosynthesis Sporobolomyces coprophilus 8-amino-7-oxononanoate + CoA + CO2 i.e. 7-oxo-8-amino-pelargonic acid ? 320929 2.3.1.47 6-carboxyhexanoyl-CoA + L-alanine reaction in biotin biosynthesis Citrobacter freundii 8-amino-7-oxononanoate + CoA + CO2 i.e. 7-oxo-8-amino-pelargonic acid ? 320929 2.3.1.47 6-carboxyhexanoyl-CoA + L-alanine reaction in biotin biosynthesis Erwinia aroidea 8-amino-7-oxononanoate + CoA + CO2 i.e. 7-oxo-8-amino-pelargonic acid ? 320929 2.3.1.47 6-carboxyhexanoyl-CoA + L-alanine first committed step in the biotin biosynthesis pathway Mycobacterium tuberculosis 8-amino-7-oxononanoate + CoA + CO2 - ? 320929 2.3.1.47 6-carboxyhexanoyl-CoA + L-alanine 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 Escherichia coli 8-amino-7-oxononanoate + CoA + CO2 - ? 320929 2.3.1.47 6-carboxyhexanoyl-CoA + L-alanine a Claisen condensation Escherichia coli 8-amino-7-oxononanoate + CoA + CO2 - ? 320929 2.3.1.47 6-carboxyhexanoyl-CoA + L-alanine the L-isomer of the amino acid is preferred giving a 5fold faster reaction, interaction analysis, overview Mycobacterium tuberculosis 8-amino-7-oxononanoate + CoA + CO2 i.e. L-KAPA ? 320929 2.3.1.47 6-carboxyhexanoyl-CoA + L-serine low activity Escherichia coli 9-hydroxy-8-amino-7-oxononanoate + CoA - ? 320930 2.3.1.47 acetyl-CoA + L-arginine - Cylindrospermopsis raciborskii N-[(4S)-4-amino-5-oxohexyl]guanidine + CO2 + CoA - ? 455188 2.3.1.47 acetyl-CoA + L-arginine - Cylindrospermopsis raciborskii T3 N-[(4S)-4-amino-5-oxohexyl]guanidine + CO2 + CoA - ? 455188 2.3.1.47 benzoyl-CoA + L-arginine - Cylindrospermopsis raciborskii N-[(4S)-4-amino-5-oxo-5-phenylpentyl]guanidine + CO2 + CoA - ? 455380 2.3.1.47 benzoyl-CoA + L-arginine - Cylindrospermopsis raciborskii T3 N-[(4S)-4-amino-5-oxo-5-phenylpentyl]guanidine + CO2 + CoA - ? 455380 2.3.1.47 butanoyl-CoA + L-arginine - Cylindrospermopsis raciborskii N-[(4S)-4-amino-5-oxooctyl]guanidine + CO2 + CoA - ? 455415 2.3.1.47 butanoyl-CoA + L-arginine - Cylindrospermopsis raciborskii T3 N-[(4S)-4-amino-5-oxooctyl]guanidine + CO2 + CoA - ? 455415 2.3.1.47 cyclopentanoyl-CoA + L-arginine - Cylindrospermopsis raciborskii N-[(4S)-4-amino-5-cyclopentyl-5-oxopentyl]guanidine + CO2 + CoA - ? 455490 2.3.1.47 cyclopentanoyl-CoA + L-arginine - Cylindrospermopsis raciborskii T3 N-[(4S)-4-amino-5-cyclopentyl-5-oxopentyl]guanidine + CO2 + CoA - ? 455490 2.3.1.47 glycine + acetyl-CoA - Symbiobacterium thermophilum ? - ? 420743 2.3.1.47 glycine + acetyl-CoA - Symbiobacterium thermophilum IAM14863 ? - ? 420743 2.3.1.47 glycine + pimeloyl-CoA - Symbiobacterium thermophilum ? - ? 420744 2.3.1.47 glycine + pimeloyl-CoA - Symbiobacterium thermophilum IAM14863 ? - ? 420744 2.3.1.47 hexanoyl-CoA + L-arginine - Cylindrospermopsis raciborskii N-[(4S)-4-amino-5-oxodecyl]guanidine + CO2 + CoA - ? 455768 2.3.1.47 hexanoyl-CoA + L-arginine - Cylindrospermopsis raciborskii T3 N-[(4S)-4-amino-5-oxodecyl]guanidine + CO2 + CoA - ? 455768 2.3.1.47 indole-3-carboxylic acid + 1-(2,6-dihydroxyphenyl)-butan-1-one - Daldinia eschscholtzii indolchromin A + CO2 + H2O - ? 455789 2.3.1.47 isobutanoyl-CoA + L-arginine - Cylindrospermopsis raciborskii N-[(4S)-4-amino-6-methyl-5-oxoheptyl]guanidine + CO2 + CoA - ? 455795 2.3.1.47 isovaleryl-CoA + L-arginine - Cylindrospermopsis raciborskii N-[(4S)-4-amino-7-methyl-5-oxooctyl]guanidine + CO2 + CoA - ? 455801 2.3.1.47 L-alanine + acetyl-CoA - Symbiobacterium thermophilum ? - ? 420821 2.3.1.47 L-alanine + acetyl-CoA - Symbiobacterium thermophilum IAM14863 ? - ? 420821 2.3.1.47 L-alanine + pimeloyl-CoA - Escherichia coli 8-amino-7-oxononanoate + CoA + CO2 - ? 420823 2.3.1.47 L-alanine + pimeloyl-CoA - Arabidopsis thaliana 8-amino-7-oxononanoate + CoA + CO2 - ? 420823 2.3.1.47 L-alanine + pimeloyl-CoA - Acetivibrio thermocellus 8-amino-7-oxononanoate + CoA + CO2 - ? 420823 2.3.1.47 L-alanine + pimeloyl-CoA - Thermosynechococcus vestitus 8-amino-7-oxononanoate + CoA + CO2 - ? 420823 2.3.1.47 L-alanine + pimeloyl-CoA no activity observed with acetyl-CoA, no activity observed with glycine or L-serine Aquifex aeolicus 8-amino-7-oxononanoate + CoA + CO2 - ? 420823 2.3.1.47 L-alanine + pimeloyl-CoA no activity observed with acetyl-CoA, no activity observed with glycine or L-serine Geobacillus kaustophilus 8-amino-7-oxononanoate + CoA + CO2 - ? 420823 2.3.1.47 L-alanine + pimeloyl-CoA no activity observed with L-serine Symbiobacterium thermophilum 8-amino-7-oxononanoate + CoA + CO2 - ? 420823 2.3.1.47 L-alanine + pimeloyl-CoA no activity observed with acetyl-CoA, no activity observed with glycine or L-serine Geobacillus kaustophilus JCM 12893 8-amino-7-oxononanoate + CoA + CO2 - ? 420823 2.3.1.47 L-alanine + pimeloyl-CoA no activity observed with L-serine Symbiobacterium thermophilum IAM14863 8-amino-7-oxononanoate + CoA + CO2 - ? 420823 2.3.1.47 L-alanine + pimeloyl-CoA - Acetivibrio thermocellus ATCC 27405 8-amino-7-oxononanoate + CoA + CO2 - ? 420823 2.3.1.47 additional information the enzyme catalyzes the first committed enzyme of the biotin synthesis pathway Arabidopsis thaliana ? - ? 89 2.3.1.47 additional information pimeloyl-CoA forms a quinonoid with L- or D-KAPA Mycobacterium tuberculosis ? - ? 89 2.3.1.47 additional information the enzyme is unable to utilize pimeloyl-[acyl carrier protein] Bacillus subtilis ? - - 89 2.3.1.47 additional information the enzyme is unable to utilize pimeloyl-[acyl carrier protein] Bacillus subtilis 168 ? - - 89 2.3.1.47 octanoyl-CoA + L-arginine - Cylindrospermopsis raciborskii N-[(4S)-4-amino-5-oxododecyl]guanidine + CO2 + CoA - ? 456119 2.3.1.47 pimeloyl-CoA + D-alanine - Mycobacterium tuberculosis ? - ? 389565 2.3.1.47 pimeloyl-CoA + L-alanine - Arabidopsis thaliana 8-amino-7-oxononanoate + CoA + CO2 - ? 386665 2.3.1.47 pimeloyl-CoA + L-alanine the enzyme is strictly stereospecific for L-alanine Arabidopsis thaliana 8-amino-7-oxononanoate + CoA + CO2 - ? 386665 2.3.1.47 pimeloyl-CoA + L-alanine - Mycobacterium tuberculosis ? - ? 389567 2.3.1.47 pimeloyl-CoA + L-alanine - Escherichia coli 8-amino-7-oxononanoate + CO2 + CoA - ? 456275 2.3.1.47 pimeloyl-CoA + L-alanine - Bacillus subtilis 8-amino-7-oxononanoate + CO2 + CoA - ? 456275 2.3.1.47 pimeloyl-CoA + L-alanine - Bacillus subtilis 168 8-amino-7-oxononanoate + CO2 + CoA - ? 456275 2.3.1.47 pimeloyl-CoA + L-alanine methyl ester trapping and determination of the reaction intermediate using the the more stable methyl ester of the substrate, overview Escherichia coli ? - ? 389566 2.3.1.47 pimeloyl-[acyl carrier protein] + L-alanine - Escherichia coli 8-amino-7-oxononanoate + CO2 + [acyl carrier protein] - ? 456274 2.3.1.47 pimeloyl-[acyl-carrier protein] + L-alanine - Arabidopsis thaliana 8-amino-7-oxononanoate + CO2 + holo-[acyl-carrier protein] - ? 434723 2.3.1.47 pimeloyl-[acyl-carrier protein] + L-alanine - Mycolicibacterium smegmatis 8-amino-7-oxononanoate + CO2 + holo-[acyl-carrier protein] - ? 434723 2.3.1.47 pimeloyl-[acyl-carrier protein] + L-alanine - Mycolicibacterium smegmatis ATCC 700084 8-amino-7-oxononanoate + CO2 + holo-[acyl-carrier protein] - ? 434723 2.3.1.47 propionyl-CoA + L-arginine - Cylindrospermopsis raciborskii N-[(4S)-4-amino-5-oxoheptyl]guanidine + CO2 + CoA - ? 456301 2.3.1.47 propionyl-[acyl-carrier protein] + L-alanine - Cylindrospermopsis raciborskii 1-[(4S)-4-amino-5-oxoheptyl]guanidine + CO2 + holo-[acyl-carrier protein] - ? 456304 2.3.1.47 propionyl-[acyl-carrier protein] + L-arginine - Cylindrospermopsis raciborskii N-[(4S)-4-amino-5-oxoheptyl]guanidine + CO2 + holo-[acyl-carrier protein] - ? 456305