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

Synonyms: a (Z)-octadec-11-enoyl-[acp], a (Z)-octadec-11-enoyl-[acyl-carrier-protein], a cis-vaccenoyl-[acyl-carrier protein]

Superclasses: a modified proteinan acyl-[acyl-carrier protein]a 2,3,4-saturated fatty acyl-[acp]
a modified proteinan acyl-[acyl-carrier protein]a long-chain acyl-[acyl-carrier protein]
a modified proteinan acyl-[acyl-carrier protein]a mono-unsaturated acyl-[acp]a cis-octadec-11-enoyl-[acyl-carrier protein] (n-C18:1)


Summary:
cis-Vaccenate is produced from palmitoleate by bacteria and plants. It is one of only two unsaturated fatty acids in Escherichia coli [Garwin80] (see cis-vaccenate biosynthesis). Some plant species such as Asclepias syriaca and Dolichandra unguis-cati (Doxantha unguis-cati L.) produce relatively high levels of palmitoleate and cis-vaccenate in their seed oils [Chisholm60, Chisholm65]. The plant pathway is likely identical to the bacterial one (in [Nguyen10a]).

Like other fatty acids, cis-vaccenate is rarely found in its free form. It is usually found as either cis-vaccenoyl-[acp] or incorporated into a lipid.

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][periplasm] + H2O[periplasm]cis-vaccenate[periplasm] + a holo-[acyl-carrier protein][periplasm] + H+[periplasm]

Not in pathways:
a cis-vaccenoyl-[acp] + sn-glycerol 3-phosphate → 1-cis-vaccenoylglycerol-3-phosphate + a holo-[acyl-carrier protein]
a cis-vaccenoyl-[acp] + 1-palmitoylglycerol 3-phosphate → 1-palmitoyl-2-cis-vaccenoyl phosphatidate + a holo-[acyl-carrier protein]
a cis-vaccenoyl-[acp] + 1-cis-vaccenoylglycerol-3-phosphate → 1,2-dicis-vaccenoyl-phosphatidate + a holo-[acyl-carrier protein]

fatty acid elongation -- saturated :
a malonyl-[acp] + a 2,3,4-saturated fatty acyl-[acp] + H+ → a holo-[acyl-carrier protein] + a 3-oxoacyl-[acp] + CO2

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

fatty acid elongation -- saturated :
a 2,3,4-saturated fatty acyl-[acp] + NAD+ ← a trans-2-enoyl-[acyl-carrier protein] + NADH + H+
a 2,3,4-saturated fatty acyl-[acp] + NADP+ ← a trans-2-enoyl-[acyl-carrier protein] + NADPH + H+

Not in pathways:
ATP + a holo-[acyl-carrier protein] + a fatty acid → AMP + a 2,3,4-saturated fatty acyl-[acp] + diphosphate

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:
a 2,3,4-saturated 2-lysophosphatidate + a 2,3,4-saturated fatty acyl-[acp] = a 2,3,4-saturated L-phosphatidate + a holo-[acyl-carrier protein]

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 [Heath96, 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

Chisholm60: Chisholm MJ, Hopkins C Y (1960). "11-octadecenoic acid and other fatty acids of Asclepias syriaca seed oil." Canadian Journal of Chemistry 38(6);805-812.

Chisholm65: Chisholm MJ, Hopkins C Y (1965). "Fatty acids of doxantha seed oil." Journal of the American Oil Chemists' Society 42(1);49-50.

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

Garwin80: Garwin JL, Klages AL, Cronan JE (1980). "Beta-ketoacyl-acyl carrier protein synthase II of Escherichia coli. Evidence for function in the thermal regulation of fatty acid synthesis." J Biol Chem 1980;255(8);3263-5. PMID: 6988423

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

Heath96: 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

Heath96a: 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

Nguyen10a: Nguyen HT, Mishra G, Whittle E, Pidkowich MS, Bevan SA, Merlo AO, Walsh TA, Shanklin J (2010). "Metabolic engineering of seeds can achieve levels of omega-7 fatty acids comparable with the highest levels found in natural plant sources." Plant Physiol 154(4);1897-904. PMID: 20943853


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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 Pathway Tools version 19.5 (software by SRI International) on Mon Feb 8, 2016, biocyc13.