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Escherichia coli K-12 substr. MG1655 Protein Class: a cis-vaccenoyl-[acp]

Synonyms: a (Z)-3-oxooctadec-13-enoyl-[acp], a (Z)-3-oxooctadec-13-enoyl-[acyl-carrier-protein], a cis-vaccenoyl-[acyl-carrier protein]

Superclasses: a modified protein an acyl-protein thioester an acyl-[acyl-carrier protein] a mono-unsaturated acyl-[acp]

a <i>cis</i>-vaccenoyl-[acp] compound structure

SMILES: CCCCCCC=CCCCCCCCCCC(SCCNC(=O)CCNC(C(O)C(C)(C)COP(=O)([O-])OCC(N[an apo-[acyl-carrier protein]])C(=O)[an apo-[acyl-carrier protein]])=O)=O

Reactions known to consume the compound:

cis-vaccenate biosynthesis :
a cis-vaccenoyl-[acp][periplasmic space] + H2O[periplasmic space]cis-vaccenate[periplasmic space] + a holo-[acyl-carrier protein][periplasmic space] + H+[periplasmic space]

CDP-diacylglycerol biosynthesis II :
a 1-acyl-sn-glycerol 3-phosphate + an acyl-[acyl-carrier protein] → a 1,2-diacyl-sn-glycerol 3-phosphate + a holo-[acyl-carrier protein]
sn-glycerol 3-phosphate + an acyl-[acyl-carrier protein] → a 1-acyl-sn-glycerol 3-phosphate + a holo-[acyl-carrier protein]

Reactions known to produce the compound:

cis-vaccenate biosynthesis :
a (2-trans-11-cis)-vaccen-2-enoyl-[acp] + NADH + H+a cis-vaccenoyl-[acp] + NAD+

Reactions known to both consume and produce the compound:

Not in pathways:
an acyl-[acyl-carrier protein] + a 2-acyl-1-lyso-phosphatidylethanolamine ↔ a holo-[acyl-carrier protein] + an L-1-phosphatidylethanolamine

In Reactions of unknown directionality:

Not in pathways:
an acyl-[acyl-carrier protein] + NAD+ = a trans-2-enoyl-[acyl-carrier protein] + NADH + H+
an acyl-[acyl-carrier protein] + a malonyl-[acp] + H+ = a 3-oxoacyl-[acp] + CO2 + a holo-[acyl-carrier protein]

Enzymes inhibited by a cis-vaccenoyl-[acp], sorted by the type of inhibition, are:

Inhibitor (Competitive) of: β-ketoacyl-ACP synthase [Comment 1]

Inhibitor (Mechanism unknown) of: acetyl-CoA carboxyltransferase [Davis01] , 2,3,4-saturated fatty acyl-[acp]:NAD+ oxidoreductase [Heath95, Comment 2]

Inhibitor (Other types) of: β-ketoacyl-ACP synthase [Heath96a, Comment 3]

This compound has been characterized as an alternative substrate of the following enzymes: acyl-CoA:sn-glycerol-3-phosphate 1-O-acyltransferase , acyl-CoA:1-acyl-sn-glycerol-3-phosphate 2-O-acyltransferase


References

Davis01: Davis MS, Cronan, Jr. JE (2001). "Inhibition of Escherichia coli acetyl coenzyme A carboxylase by acyl-acyl carrier protein." J Bacteriol. 183(4):1499-503. PMID: 11157970

Heath95: Heath RJ, Rock CO (1995). "Enoyl-acyl carrier protein reductase (fabI) plays a determinant role in completing cycles of fatty acid elongation in Escherichia coli." J Biol Chem 270(44);26538-42. PMID: 7592873

Heath96a: Heath RJ, Rock CO (1996). "Inhibition of beta-ketoacyl-acyl carrier protein synthase III (FabH) by acyl-acyl carrier protein in Escherichia coli." J Biol Chem 1996;271(18);10996-1000. PMID: 8631920

Heath96b: Heath RJ, Rock CO (1996). "Regulation of fatty acid elongation and initiation by acyl-acyl carrier protein in Escherichia coli." J Biol Chem 1996;271(4);1833-6. PMID: 8567624


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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 19.0 on Tue Sep 1, 2015, biocyc14.