NEOLIPID ENZYMATIC-SYNTHESIS - ACYLATED AMINOPOLYOLS

Enzymatic coupling of aminopolyols and medium-chain length fatty acids was carried out via the reverse action of a fungal lipase. Model reac tants and catalysts were glucamine (1-amino-1-deoxysorbitol = AmS), pe largonic (nonanoic) acid, and Lipozyme IM-20. These reactants were sel ected since aminosorbitol is both a precursor for deoxynojirimycin (di etetic inhibitor for glucosidase) and for N-methyl-glucamine (an antil eishmanial drug when complexed with antimony), and pelargonic acid is known to generate biotin-vitamers in some bacteria. The reaction proce eded in the presence of dry or water-saturated apolar organic solvents such as hexane and carbon tetrachloride. Increased molar ratio of acy l donor to acyl acceptor allowed the esterification and the amidation reactions to proceed with no need of solvent addition. A broad specifi city was found for Lypozyme reverse action in terms of both acyl accep tors and donors.