Biotin metabolism - Caldivirga maquilingensis

Biotin (vitamin H or vitamin B7) is the essential cofactor of biotin-dependent carboxylases, such as pyruvate carboxylase and acetyl-CoA carboxylase. Mammals cannot synthesize biotin, while in bacteria, fungi, and plants it is synthesized from pimelate thioester through different pathways. In E. coli and many organisms, pimelate thioester is derived from malonyl-ACP. The pathway starts with the methylation to malonyl-ACP methyl ester, followed by the fatty acid chain elongation cycle to form pimeloyl-ACP methyl ester, which is then demethylated to form pimeloyl-ACP [MD:M00572]. Pimeloyl-ACP is converted to biotin through the final four steps in the biotin bicyclic ring assembly, which are conserved among biotin-producing organisms [MD:M00123]. In B. subtilis, biotin is derived from pimeloyl-ACP formed by oxidative cleavage of long-chain acyl-ACPs [MD:M00573]. Some bacteria synthesize biotin from pimeloyl-CoA derived from pimelate [MD:M00577]. Biotin is covalently attached to biotin-dependent carboxylase by biotin protein ligase, also known as holocarboxylase synthase in mammals, to form an active holocarboxylase. After degradation of the biotinylated carboxylase into biocytin, it is further degraded by biotinidase to release free biotin, which is recycled in holocarboxylase synthesis. Biotin is catabolized by beta-oxidation of the valeric acid side chain or oxidation of sulfur in the heterocyclic ring.

Metabolism; Metabolism of cofactors and vitamins

Caldivirga maquilingensis [GN:cma]

PMID:21437340

Lin S, Cronan JE

Closing in on complete pathways of biotin biosynthesis.

Mol Biosyst 7:1811-21 (2011)

PMID:22965231

Lin S, Cronan JE

The BioC O-Methyltransferase Catalyzes Methyl Esterification of Malonyl-Acyl Carrier Protein, an Essential Step in Biotin Synthesis.

J Biol Chem 287:37010-20 (2012)

PMID:20693992

Lin S, Hanson RE, Cronan JE

Biotin synthesis begins by hijacking the fatty acid synthetic pathway.

Nat Chem Biol 6:682-8 (2010)

PMID:21435937

Cronan JE, Lin S

Synthesis of the alpha,omega-dicarboxylic acid precursor of biotin by the canonical fatty acid biosynthetic pathway.

Curr Opin Chem Biol 15:407-13 (2011)

PMID:11368323

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PMID:18838690

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Structural insights from a P450 Carrier Protein complex reveal how specificity is achieved in the P450(BioI) ACP complex.

Proc Natl Acad Sci U S A 105:15696-701 (2008)

PMID:8763940

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PMID:1445232

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PMID:12368242

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PMID:11320134

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The bio operon on the acquired symbiosis island of Mesorhizobium sp. strain R7A includes a novel gene involved in pimeloyl-CoA synthesis.

Microbiology 147:1315-22 (2001)

PMID:12039741

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Functional analysis of Sinorhizobium meliloti genes involved in biotin synthesis  and transport.

Appl Environ Microbiol 68:2843-8 (2002)

PMID:19319844

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PMID:9022537

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PMID:5775781

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Bacterial degradation of biotin. 3. Metabolism of 14C-carbonyl-labeled biotin.

J Biol Chem 244:1393-8 (1969)

PMID:2180922

Pierson DE, Campbell A

Cloning and nucleotide sequence of bisC, the structural gene for biotin sulfoxide reductase in Escherichia coli.

J Bacteriol 172:2194-8 (1990)

PMID:15601707

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Methionine sulfoxide reduction and assimilation in Escherichia coli: new role for the biotin sulfoxide reductase BisC.

J Bacteriol 187:231-7 (2005)

PMID:374979

del Campillo-Campbell A, Dykhuizen D, Cleary PP

Enzymic reduction of d-biotin d-sulfoxide to d-biotin.

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PMID:9013576

Pollock VV, Barber MJ

Biotin sulfoxide reductase. Heterologous expression and characterization of a functional molybdopterin guanine dinucleotide-containing enzyme.

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PMID:15366932

Nelson KJ, Rajagopalan KV

Studies on the interaction of NADPH with Rhodobacter sphaeroides biotin sulfoxide reductase.

Biochemistry 43:11226-37 (2004)

PMID:16299174

Pinon V, Ravanel S, Douce R, Alban C

Biotin synthesis in plants. The first committed step of the pathway is catalyzed  by a cytosolic 7-keto-8-aminopelargonic acid synthase.

Plant Physiol 139:1666-76 (2005)