Synthesis of methyl (Z)-tetracos-5-enoate and both enantiomers of ethyl (E)-6-methyltetracos-4-enoate: possible intermediates in the biosynthesis of mycolic acids in mycobacteria.
The high molecular weight 2-alkyl-3-hydroxy mycolic acids are key structural components of the cell envelope of pathogenic mycobacteria, such as Mycobacterium tuberculosis. A prime target for action would be the initial stages where the biosynthetic pathways diverge from those of ordinary fatty acids. It has been postulated that the pathway for the alpha-mycolates, without oxygen functions in addition to the hydroxy-acid unit, appears to diverge from (Z)-tetracos-5-enoic acid. The biosynthesis of oxygenated mycolic acids is considered to possibly diverge from (E)-6-(R)-methyltetracos-4-enoic and (E)-6-(S)-methyltetracos-4-enoic acids. This communication describes the synthesis of esters of these acids in order to test their potential role in the biosynthesis of mycolic acids.
Besra
G S
GS
Department of Chemistry, University of Newcastle, Newcastle upon Tyne, UK.
Minnikin
D E
DE
Wheeler
P R
PR
Ratledge
C
C
D005229:Fatty Acids, Monounsaturated / Q000138:chemical synthesis* / Q000737:chemistry; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D015394:Molecular Structure; D009161:Mycobacterium / Q000378:metabolism*; D009169:Mycobacterium tuberculosis / Q000378:metabolism*; D009171:Mycolic Acids / Q000378:metabolism*; D013055:Spectrophotometry, Infrared; D013237:Stereoisomerism
D005229:Fatty Acids, Monounsaturated; D007202:Indicators and Reagents; D009171:Mycolic Acids; C086130:ethyl 6-methyltetracos-4-enoate; C086129:methyl tetracos-5-enoate