STEREOSPECIFIC SYNTHESIS OF SELECTED TRIGLYCERIDES - COMMENTS ON ACYLMIGRATION AND ANALYSIS OF CONFIGURATION

Symmetrical and stereospecifically defined triglycerides have been pre pared from racemic and (R)- and (S)-glycidol, respectively. The synthe tic sequence allows the incorporation of sensitive fatty acids such as linolenic acid. Justification for retention of configuration and abse nce of acyl migrations during the synthesis is provided by the H-1-NMR spectra of triglycerides that are replaced at the sn-1 and sn-3 posit ions with enantiomers of alpha-methoxytrifluoromethylphenylacetic acid (bis-MTPA esters). Partial hydrolysis of synthetic symmetrical trigly cerides catalyzed by the lipase of Rhizopus oryzae was used to demonst rate the homogeneity of these preparations.