KEGG   PATHWAY: apw00780Help
Entry
apw00780                    Pathway                                

Name
Biotin metabolism - Acetobacter pasteurianus IFO 3283-01-42C
Description
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.
Class
Metabolism; Metabolism of cofactors and vitamins
BRITE hierarchy
Pathway map
Biotin metabolism
apw00780

All organismsOrtholog table
Module
Biotin biosynthesis, pimeloyl-ACP/CoA => biotin [PATH:apw00780]
Pimeloyl-ACP biosynthesis, BioC-BioH pathway, malonyl-ACP => pimeloyl-ACP [PATH:apw00780]
Other DBs
BSID: 
GO: 
Organism
Acetobacter pasteurianus IFO 3283-01-42C [GN:apw]
Gene
biotin synthesis protein; K01935 dethiobiotin synthetase [EC:6.3.3.3] K02169 malonyl-CoA O-methyltransferase [EC:2.1.1.197] [KO:K01935 K02169] [EC:6.3.3.3 2.1.1.197]
3-oxoacyl-[acyl-carrier-protein (ACP)] synthase II; K09458 3-oxoacyl-[acyl-carrier-protein] synthase II [EC:2.3.1.179] [KO:K09458] [EC:2.3.1.179]
oxidoreductase; K00059 3-oxoacyl-[acyl-carrier protein] reductase [EC:1.1.1.100] [KO:K00059] [EC:1.1.1.100]
3-oxoacyl-ACP reductase; K00059 3-oxoacyl-[acyl-carrier protein] reductase [EC:1.1.1.100] [KO:K00059] [EC:1.1.1.100]
fabZ; (3R)-hydroxymyristoyl-ACP dehydratase [KO:K02372] [EC:4.2.1.59]
enoyl-(acyl-carrier-protein) reductase; K00208 enoyl-[acyl-carrier protein] reductase I [EC:1.3.1.9 1.3.1.10] [KO:K00208] [EC:1.3.1.10 1.3.1.9]
hypothetical protein; K02170 pimeloyl-[acyl-carrier protein] methyl ester esterase [EC:3.1.1.85] [KO:K02170] [EC:3.1.1.85]
serine palmitoyltransferase; K00652 8-amino-7-oxononanoate synthase [EC:2.3.1.47] [KO:K00652] [EC:2.3.1.47]
8-amino-7-oxononanoate synthase; K00652 8-amino-7-oxononanoate synthase [EC:2.3.1.47] [KO:K00652] [EC:2.3.1.47]
adenosylmethionine-8-amino-7-oxononanoate aminotransferase; K00833 adenosylmethionine-8-amino-7-oxononanoate aminotransferase [EC:2.6.1.62] [KO:K00833] [EC:2.6.1.62]
biotin synthase; K01012 biotin synthase [EC:2.8.1.6] [KO:K01012] [EC:2.8.1.6]
biotin--acetyl-CoA-carboxylase ligase; K03524 BirA family transcriptional regulator, biotin operon repressor / biotin-[acetyl-CoA-carboxylase] ligase [EC:6.3.4.15] [KO:K03524] [EC:6.3.4.15]
Compound
C00047  
L-Lysine
C00086  
Urea
C00120  
Biotin
C01037  
7,8-Diaminononanoate
C01063  
6-Carboxyhexanoyl-CoA
C01092  
8-Amino-7-oxononanoate
C01209  
Malonyl-[acyl-carrier protein]
C01894  
Biotinyl-CoA
C01909  
Dethiobiotin
C02656  
Pimelate
C05552  
Biocytin
C05921  
Biotinyl-5'-AMP
C06250  
Holo-[carboxylase]
C19673  
Malonyl-[acp] methyl ester
C19845  
Pimeloyl-[acyl-carrier protein]
C19846  
Pimeloyl-[acyl-carrier protein] methyl ester
C20372  
3-Ketoglutaryl-[acp] methyl ester
C20373  
3-Hydroxyglutaryl-[acp] methyl ester
C20374  
Enoylglutaryl-[acp] methyl ester
C20375  
Glutaryl-[acp] methyl ester
C20376  
3-Ketopimeloyl-[acp] methyl ester
C20377  
3-Hydroxypimeloyl-[acp] methyl ester
C20378  
Enoylpimeloyl-[acp] methyl ester
C20384  
Bisnorbiotin
C20385  
Tetranorbiotin
C20386  
Biotin sulfoxide
C20387  
Biotin sulfone
C20683  
Long-chain acyl-[acyl-carrier protein]
Reference
  Authors
Lin S, Cronan JE
  Title
Closing in on complete pathways of biotin biosynthesis.
  Journal
Mol Biosyst 7:1811-21 (2011)
Reference
  Authors
Lin S, Cronan JE
  Title
The BioC O-methyltransferase catalyzes methyl esterification of malonyl-acyl carrier protein, an essential step in biotin synthesis.
  Journal
J Biol Chem 287:37010-20 (2012)
Reference
  Authors
Lin S, Hanson RE, Cronan JE
  Title
Biotin synthesis begins by hijacking the fatty acid synthetic pathway.
  Journal
Nat Chem Biol 6:682-8 (2010)
Reference
  Authors
Cronan JE, Lin S
  Title
Synthesis of the alpha,omega-dicarboxylic acid precursor of biotin by the canonical fatty acid biosynthetic pathway.
  Journal
Curr Opin Chem Biol 15:407-13 (2011)
Reference
  Authors
Stok JE, De Voss J
  Title
Expression, purification, and characterization of BioI: a carbon-carbon bond cleaving cytochrome P450 involved in biotin biosynthesis in Bacillus subtilis.
  Journal
Arch Biochem Biophys 384:351-60 (2000)
Reference
  Authors
Cryle MJ, Schlichting I
  Title
Structural insights from a P450 Carrier Protein complex reveal how specificity is achieved in the P450(BioI) ACP complex.
  Journal
Proc Natl Acad Sci U S A 105:15696-701 (2008)
Reference
PMID:8763940
  Authors
Bower S, Perkins JB, Yocum RR, Howitt CL, Rahaim P, Pero J
  Title
Cloning, sequencing, and characterization of the Bacillus subtilis biotin biosynthetic operon.
  Journal
J Bacteriol 178:4122-30 (1996)
Reference
PMID:1445232
  Authors
Ploux O, Soularue P, Marquet A, Gloeckler R, Lemoine Y
  Title
Investigation of the first step of biotin biosynthesis in Bacillus sphaericus. Purification and characterization of the pimeloyl-CoA synthase, and uptake of pimelate.
  Journal
Biochem J 287 ( Pt 3):685-90 (1992)
Reference
  Authors
Rodionov DA, Mironov AA, Gelfand MS
  Title
Conservation of the biotin regulon and the BirA regulatory signal in Eubacteria and Archaea.
  Journal
Genome Res 12:1507-16 (2002)
Reference
  Authors
Sullivan JT, Brown SD, Yocum RR, Ronson CW
  Title
The bio operon on the acquired symbiosis island of Mesorhizobium sp. strain R7A includes a novel gene involved in pimeloyl-CoA synthesis.
  Journal
Microbiology 147:1315-22 (2001)
Reference
  Authors
Entcheva P, Phillips DA, Streit WR
  Title
Functional analysis of Sinorhizobium meliloti genes involved in biotin synthesis  and transport.
  Journal
Appl Environ Microbiol 68:2843-8 (2002)
Reference
  Authors
Zempleni J, Wijeratne SS, Hassan YI
  Title
Biotin.
  Journal
Biofactors 35:36-46 (2009)
Reference
PMID:9022537
  Authors
Zempleni J, McCormick DB, Mock DM
  Title
Identification of biotin sulfone, bisnorbiotin methyl ketone, and tetranorbiotin-l-sulfoxide in human urine.
  Journal
Am J Clin Nutr 65:508-11 (1997)
Reference
PMID:5775781
  Authors
Iwahara S, McCormick DB, Wright LD, Li HC
  Title
Bacterial degradation of biotin. 3. Metabolism of 14C-carbonyl-labeled biotin.
  Journal
J Biol Chem 244:1393-8 (1969)
Reference
PMID:2180922
  Authors
Pierson DE, Campbell A
  Title
Cloning and nucleotide sequence of bisC, the structural gene for biotin sulfoxide reductase in Escherichia coli.
  Journal
J Bacteriol 172:2194-8 (1990)
Reference
  Authors
Ezraty B, Bos J, Barras F, Aussel L
  Title
Methionine sulfoxide reduction and assimilation in Escherichia coli: new role for the biotin sulfoxide reductase BisC.
  Journal
J Bacteriol 187:231-7 (2005)
Reference
PMID:374979
  Authors
del Campillo-Campbell A, Dykhuizen D, Cleary PP
  Title
Enzymic reduction of d-biotin d-sulfoxide to d-biotin.
  Journal
Methods Enzymol 62:379-85 (1979)
Reference
PMID:9013576
  Authors
Pollock VV, Barber MJ
  Title
Biotin sulfoxide reductase. Heterologous expression and characterization of a functional molybdopterin guanine dinucleotide-containing enzyme.
  Journal
J Biol Chem 272:3355-62 (1997)
Reference
  Authors
Nelson KJ, Rajagopalan KV
  Title
Studies on the interaction of NADPH with Rhodobacter sphaeroides biotin sulfoxide reductase.
  Journal
Biochemistry 43:11226-37 (2004)
Reference
  Authors
Pinon V, Ravanel S, Douce R, Alban C
  Title
Biotin synthesis in plants. The first committed step of the pathway is catalyzed  by a cytosolic 7-keto-8-aminopelargonic acid synthase.
  Journal
Plant Physiol 139:1666-76 (2005)
KO pathway
 

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