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Escherichia coli K-12 substr. MG1655 Enzyme: malonyl-[acp] methyltransferase



Gene: bioC Accession Numbers: EG10119 (EcoCyc), b0777, ECK0766

Regulation Summary Diagram: ?

Summary:
BioC is a methyltransferase involved in an early step of biotin biosynthesis [Del67, Rolfe68, Otsuka88]. It is thought to methylate the ω-carboxyl group of malonyl-[acp] to form a malonyl-[acp] methyl ester, which is recognized by the fatty acid synthetic enzymes [Lin10]. The methyl ester is processed via the fatty acid elongation cycle to give a pimeloyl-[acp] methyl ester, which is processed into pimelyl-[acp] by BioH [Lin10].

For a long time, neither the exact function of BioC nor the path to pimelate was understood. Lemoine et al. ([Lemoine96]) proposed that BioC may catalyze the stepwise condensation of malonyl-CoA by addition of acetate units. [ORegan89] cites unpublished results showing lack of growth of a bioC mutant on pimelate, but 13C tracing indicated that pimelate is not a precursor of biotin [Ifuku94]. The function of BioC was finally suggested in a 2010 study [Lin10]. Due to difficulties studying the E. coli enzyme in vitro, the biochemical function of the Bacillus cereus enzyme was determined; expression of this enzyme complements an E. coli bioC mutant [Lin12d].

bioC mutants require biotin for growth [Del67] and appear to be blocked before the synthesis of pimeloyl-CoA [Cleary72]. Monomethyl esters of malonate, glutarate and pimelate allow growth of a bioC deletion mutant in the presence of a heterologous acyl-ACP synthetase that converts these compounds to ACP thioesters [Lin10].

Review: [Lin11c]

Gene Citations: [Nath82]

Locations: cytosol

Map Position: [810,745 -> 811,500] (17.47 centisomes)
Length: 756 bp / 251 aa

Molecular Weight of Polypeptide: 28.276 kD (from nucleotide sequence)

Unification Links: ASAP:ABE-0002648 , CGSC:957 , EchoBASE:EB0117 , EcoGene:EG10119 , EcoliWiki:b0777 , ModBase:P12999 , OU-Microarray:b0777 , PortEco:bioC , PR:PRO_000022223 , Pride:P12999 , Protein Model Portal:P12999 , RefSeq:NP_415298 , RegulonDB:EG10119 , SMR:P12999 , String:511145.b0777 , UniProt:P12999

Relationship Links: InterPro:IN-FAMILY:IPR011814 , InterPro:IN-FAMILY:IPR013216 , Pfam:IN-FAMILY:PF08241

In Paralogous Gene Group: 194 (13 members)

Gene-Reaction Schematic: ?

Genetic Regulation Schematic: ?

GO Terms:

Biological Process: GO:0009102 - biotin biosynthetic process Inferred from experiment Inferred by computational analysis [UniProtGOA12, UniProtGOA11, GOA01, Del67]
GO:0008152 - metabolic process Inferred by computational analysis [GOA01]
GO:0032259 - methylation Inferred by computational analysis [UniProtGOA11]
Molecular Function: GO:0010340 - carboxyl-O-methyltransferase activity Inferred from experiment Inferred by computational analysis [GOA01, Lin10]
GO:0008168 - methyltransferase activity Inferred by computational analysis [UniProtGOA11, GOA01]
GO:0016740 - transferase activity Inferred by computational analysis [UniProtGOA11]
Cellular Component: GO:0005829 - cytosol Inferred by computational analysis [DiazMejia09]

MultiFun Terms: metabolism biosynthesis of building blocks cofactors, small molecule carriers biotin

Essentiality data for bioC knockouts: ?

Growth Medium Growth? T (°C) O2 pH Osm/L Growth Observations
LB enriched Yes 37 Aerobic 6.95   Yes [Gerdes03, Comment 1]
LB Lennox Yes 37 Aerobic 7   Yes [Baba06, Comment 2]
M9 medium with 0.4% glucose No 37 Aerobic 7.2 0.27 No [Patrick07, Comment 3]
M9 medium with 1% glycerol Yes 37 Aerobic 7.2 0.35 Yes [Joyce06, Comment 4]
MOPS medium with 0.4% glucose Yes 37 Aerobic 7.2 0.22 Yes [Baba06, Comment 2]

Credits:
Curated 17-Aug-2010 by Caspi R , SRI International
Last-Curated ? 25-Oct-2012 by Keseler I , SRI International


Enzymatic reaction of: malonyl-CoA methyltransferase (malonyl-[acp] methyltransferase)

EC Number: 2.1.1.197

a malonyl-[acp] + S-adenosyl-L-methionine <=> a malonyl-[acp] methyl ester + S-adenosyl-L-homocysteine

The reaction direction shown, that is, A + B ↔ C + D versus C + D ↔ A + B, is in accordance with the Enzyme Commission system.

The reaction is physiologically favored in the direction shown.

In Pathways: biotin biosynthesis I , 8-amino-7-oxononanoate biosynthesis I


Sequence Features

Feature Class Location Citations Comment
Sequence-Conflict 149
[Otsuka88, UniProt10a]
Alternate sequence: L → R; UniProt: (in Ref. 1; AAA23517);


Gene Local Context (not to scale): ?

Transcription Units:

Notes:

History:
10/20/97 Gene b0777 from Blattner lab Genbank (v. M52) entry merged into EcoCyc gene EG10119; confirmed by SwissProt match.


References

Baba06: Baba T, Ara T, Hasegawa M, Takai Y, Okumura Y, Baba M, Datsenko KA, Tomita M, Wanner BL, Mori H (2006). "Construction of Escherichia coli K-12 in-frame, single-gene knockout mutants: the Keio collection." Mol Syst Biol 2;2006.0008. PMID: 16738554

Cleary72: Cleary PP, Campbell A (1972). "Deletion and complementation analysis of biotin gene cluster of Escherichia coli." J Bacteriol 112(2);830-9. PMID: 4563978

Del67: Del Campillo-Campbell A, Kayajanian G, Campbell A, Adhya S (1967). "Biotin-requiring mutants of Escherichia coli K-12." J Bacteriol 94(6);2065-6. PMID: 4864413

DiazMejia09: Diaz-Mejia JJ, Babu M, Emili A (2009). "Computational and experimental approaches to chart the Escherichia coli cell-envelope-associated proteome and interactome." FEMS Microbiol Rev 33(1);66-97. PMID: 19054114

Gerdes03: Gerdes SY, Scholle MD, Campbell JW, Balazsi G, Ravasz E, Daugherty MD, Somera AL, Kyrpides NC, Anderson I, Gelfand MS, Bhattacharya A, Kapatral V, D'Souza M, Baev MV, Grechkin Y, Mseeh F, Fonstein MY, Overbeek R, Barabasi AL, Oltvai ZN, Osterman AL (2003). "Experimental determination and system level analysis of essential genes in Escherichia coli MG1655." J Bacteriol 185(19);5673-84. PMID: 13129938

GOA01: GOA, DDB, FB, MGI, ZFIN (2001). "Gene Ontology annotation through association of InterPro records with GO terms."

Ifuku94: Ifuku O, Miyaoka H, Koga N, Kishimoto J, Haze S, Wachi Y, Kajiwara M (1994). "Origin of carbon atoms of biotin. 13C-NMR studies on biotin biosynthesis in Escherichia coli." Eur J Biochem 220(2);585-91. PMID: 8125118

Joyce06: Joyce AR, Reed JL, White A, Edwards R, Osterman A, Baba T, Mori H, Lesely SA, Palsson BO, Agarwalla S (2006). "Experimental and computational assessment of conditionally essential genes in Escherichia coli." J Bacteriol 188(23);8259-71. PMID: 17012394

Lemoine96: Lemoine Y, Wach A, Jeltsch JM (1996). "To be free or not: the fate of pimelate in Bacillus sphaericus and in Escherichia coli." Mol Microbiol 19(3);645-7. PMID: 8830257

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

Lin11c: Lin S, Cronan JE (2011). "Closing in on complete pathways of biotin biosynthesis." Mol Biosyst 7(6);1811-21. PMID: 21437340

Lin12d: Lin S, Cronan JE (2012). "The BioC O-Methyltransferase Catalyzes Methyl Esterification of Malonyl-Acyl Carrier Protein, an Essential Step in Biotin Synthesis." J Biol Chem. PMID: 22965231

Nath82: Nath SK, Guha A (1982). "Abortive termination of bioBFCD RNA synthesized in vitro from the bioABFCD operon of Escherichia coli K-12." Proc Natl Acad Sci U S A 79(6);1786-90. PMID: 6177001

ORegan89: O'Regan M, Gloeckler R, Bernard S, Ledoux C, Ohsawa I, Lemoine Y (1989). "Nucleotide sequence of the bioH gene of Escherichia coli." Nucleic Acids Res 17(19);8004. PMID: 2678009

Otsuka88: Otsuka AJ, Buoncristiani MR, Howard PK, Flamm J, Johnson C, Yamamoto R, Uchida K, Cook C, Ruppert J, Matsuzaki J (1988). "The Escherichia coli biotin biosynthetic enzyme sequences predicted from the nucleotide sequence of the bio operon." J Biol Chem 263(36);19577-85. PMID: 3058702

Patrick07: Patrick WM, Quandt EM, Swartzlander DB, Matsumura I (2007). "Multicopy suppression underpins metabolic evolvability." Mol Biol Evol 24(12);2716-22. PMID: 17884825

Rolfe68: Rolfe B, Eisenberg MA (1968). "Genetic and biochemical analysis of the biotin loci of Escherichia coli K-12." J Bacteriol 96(2);515-24. PMID: 4877129

UniProt10a: UniProt Consortium (2010). "UniProt version 2010-11 released on 2010-11-02 00:00:00." Database.

UniProtGOA11: UniProt-GOA (2011). "Gene Ontology annotation based on manual assignment of UniProtKB keywords in UniProtKB/Swiss-Prot entries."

UniProtGOA12: UniProt-GOA (2012). "Gene Ontology annotation based on UniPathway vocabulary mapping."

Other References Related to Gene Regulation

AbdelHamid07: Abdel-Hamid AM, Cronan JE (2007). "Coordinate expression of the acetyl coenzyme A carboxylase genes, accB and accC, is necessary for normal regulation of biotin synthesis in Escherichia coli." J Bacteriol 189(2);369-76. PMID: 17056747

Cronan89: Cronan JE (1989). "The E. coli bio operon: transcriptional repression by an essential protein modification enzyme." Cell 58(3);427-9. PMID: 2667763

Lin91a: Lin KC, Campbell A, Shiuan D (1991). "Binding characteristics of Escherichia coli biotin repressor-operator complex." Biochim Biophys Acta 1090(3);317-25. PMID: 1659455

Otsuka78: Otsuka A, Abelson J (1978). "The regulatory region of the biotin operon in Escherichia coli." Nature 1978;276(5689);689-94. PMID: 366433


Report Errors or Provide Feedback
Please cite the following article in publications resulting from the use of EcoCyc: Nucleic Acids Research 41:D605-12 2013
Page generated by SRI International Pathway Tools version 18.5 on Sun Nov 23, 2014, BIOCYC14A.