Synthesis of mycocerosic acids from methylmalonyl coenzyme A by cell-free extracts of Mycobacterium tuberculosis var. bovis BCG.

Abstract

Multimethyl-branched acids extracted from the cells of Mycobacterium tuberculosis var. bovis BCG were identified by combined capillary gas-liquid chromatography and mass spectrometry. These mycocerosic acids consisted of the products expected from elongation of n-C18 and n-C20 primers with methylmalonyl-CoA. A soluble enzyme preparation from M. tuberculosis var. bovis BCG incorporated methylmalonyl-CoA into mycocerosic acids. This incorporation was partially dependent on the addition of arachidoyl-CoA and this primer affected product distribution, indicating elongation of the primer. Maximal incorporation of methylmalonyl-CoA required the presence of both NADPH and NADH together with ATP and Mg2+. Added CoA, FMN, acyl carrier protein, or bovine serum albumin had no effect on the activity in either the presence or absence of ATP and Mg2+. The pH optimum for mycocerosic acid synthesis was 6.2. Under these conditions, methylmalonyl-CoA was incorporated into very long acids which were identified as mycocerosic acids by radio gas-liquid chromatography.

• Authors: D L Rainwater, P E Kolattukudy
• Journal: The Journal of biological chemistry (J Biol Chem) Vol. 258 Issue 5 Pg. 2979-85 (Mar 10 1983) ISSN: 0021-9258 [Print] United States
• PMID: 6402506 (Publication Type: Journal Article, Research Support, U.S. Gov't, Non-P.H.S., Research Support, U.S. Gov't, P.H.S.)

Chemical References

• Acyl Coenzyme A
• Fatty Acids
• methylmalonyl-coenzyme A
• Malonyl Coenzyme A
• mycocerosic acid

Topics

• Acyl Coenzyme A (analogs & derivatives)
• Fatty Acids (biosynthesis)
• Gas Chromatography-Mass Spectrometry
• Kinetics
• Malonyl Coenzyme A (analogs & derivatives, metabolism)
• Mycobacterium tuberculosis (metabolism)
• Structure-Activity Relationship