Concerning hydrolysis of mycolate esters, of phthiocerol dimycocerosates and of related mycobacterial lipids: an anecdotal account.
We review the experimental difficulties that have been encountered in hydrolyzing mycolic acid esters, their beta-O-substituted analogues, permethylated cord factor, phthiocerol dimycocerosates and similar mycobacterial lipids. Hydrolysis of the beta-O-substituted methyl mycolates is invariably sluggish and is accompanied by considerable beta-elimination to generate mycolenoic acids. Historical evidence for this often undesirable side reaction is presented. Improvements in methodology are described in which hydrolysis is promoted and beta-elimination is minimized. The reaction systems developed were found applicable to hydrolysis of the quite inert phthiocerol dimycocerosates. Permethylation of the recovered phthiocerol provides an excellent derivative for mass spectrometric analysis to define its complete structure.
D004952:Esters; D006868:Hydrolysis; D008055:Lipids / Q000032:analysis*; D009161:Mycobacterium / Q000378:metabolism*; D009171:Mycolic Acids / Q000032:analysis*
D004952:Esters; D008055:Lipids; D009171:Mycolic Acids; C008901:phthiocerol dimycocerosate