Parent Class:

EC-Numbers → 2 -- Transferases → 2.3 -- Acyltransferases → 2.3.1 -- Transferring groups other than amino-acyl groups

Synonyms: 7-keto-8-aminopelargonic acid synthetase, 7-keto-8-aminopelargonic synthetase, 8-amino-7-oxopelargonate synthase, bioF (gene name)

Systematic Name: 6-carboxyhexanoyl-[acyl-carrier protein]:L-alanine C-carboxyhexanoyltransferase (decarboxylating)

Unification Links: BRENDA:2.3.1.47, ENZYME:2.3.1.47, IUBMB-ExplorEnz:2.3.1.47

Reaction:
pimeloyl-[acp] + L-alanine + H⁺ → (8S)-8-amino-7-oxononanoate + CO₂ + acyl-carrier protein

Unofficial Reactions:
pimeloyl-CoA + L-alanine + H⁺ → CO₂ + coenzyme A + (8S)-8-amino-7-oxononanoate

Enzymes and Genes:
8-amino-7-oxononanoate synthase: bioF ( Agrobacterium fabrum C58 )
8-amino-7-oxononanoate synthase: bioF ( Escherichia coli K-12 substr. MG1655 )
8-amino-7-oxononanoate synthase: bioF ( Bacillus subtilis subtilis 168 )

Summary:
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 [ [Lin10].

Citations: [Eisenberg68, Alexeev98, Ploux99, Webster00]

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References

Alexeev98: Alexeev D, Alexeeva M, Baxter RL, Campopiano DJ, Webster SP, Sawyer L (1998). "The crystal structure of 8-amino-7-oxononanoate synthase: a bacterial PLP-dependent, acyl-CoA-condensing enzyme." J Mol Biol 284(2);401-19. PMID: 9813126

Eisenberg68: Eisenberg MA, Star C (1968). "Synthesis of 7-oxo-8-aminopelargonic acid, a biotin vitamer, in cell-free extracts of Escherichia coli biotin auxotrophs." J Bacteriol 96(4);1291-7. PMID: 4879561

Lin10: Lin S, Hanson RE, Cronan JE (2010). "Biotin synthesis begins by hijacking the fatty acid synthetic pathway." Nat Chem Biol 6(9);682-8. PMID: 20693992

Ploux99: Ploux O, Breyne O, Carillon S, Marquet A (1999). "Slow-binding and competitive inhibition of 8-amino-7-oxopelargonate synthase, a pyridoxal-5'-phosphate-dependent enzyme involved in biotin biosynthesis, by substrate and intermediate analogs. Kinetic and binding studies." Eur J Biochem 259(1-2);63-70. PMID: 9914476

Webster00: Webster SP, Alexeev D, Campopiano DJ, Watt RM, Alexeeva M, Sawyer L, Baxter RL (2000). "Mechanism of 8-amino-7-oxononanoate synthase: spectroscopic, kinetic, and crystallographic studies." Biochemistry 39(3);516-28. PMID: 10642176

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Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 46(D1):D633-D639 2018
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