Kinetically controlled synthesis of monoglyceryl esters from chiral and prochiral acids methyl esters catalyzed by immobilized Rhizomucor miehei lipase.

摘要: Abstract Partial acylation of only one primary hydroxyl group glycerol generates a chiral center at position 2. Rhizomucor miehei lipase (RML) catalyzes the kinetically controlled transesterification different aromatic carboxylic acids methyl esters with glycerol. High synthetic yields glyceryl (around 70–80%) were obtained even in presence significant concentrations water (from 5% to 20%). After long incubation reaction mixture biocatalyst pure free acid was obtained. Other lipases Geobacillus thermocatenulatus and from Thermomyces lanuginose) also catalyzed similar transesterifications although less efficiently. RML immobilized on Sepharose-Q showed high activity specificity, compared immobilization by other techniques, producing monoglyceryl all substrates. In particular, monoglyceryl-phenylmalonate product synthesized 82% overall yield >99% diastereomeric excess pH 7.0 37 °C 90%