LIPASE-CATALYZED ENANTIOSELECTIVE ESTERIFICATION OR HYDROLYSIS OF 1-O-ALKYL-3-O-TOSYLGLYCEROL DERIVATIVES - PRACTICAL SYNTHESIS OF (S)-(+)-1-O-HEXADECYL-2,3-DI-O-HEXADECANOYLGLYCEROL, A MARINE NATURAL PRODUCT

Racemic 1-O-alkyl-3-O-tosylglycerol derivatives were resolved by acylation with palmitic anhydride in the presence of Pseudomonas fluorescens lipase in organic media. The reverse reaction, the enzymatic hydrolysis of 1-O-alkyl-2-O-palmitoyl-3-O-tosylglycerols in isopropyl ether saturated with water was also highly stereoselective. An efficient and simple synthesis of the naturally occurring (S)-(+)-1-O-hexadecyl-2,3-di-O-hexadecanoylglycerol based on this process is reported.