Esterification patterns of lipases for synthesizing tricaproylglycerols in organic solvent

Abstract

To investigate the synthetic patterns of triglyceride (triacylglycerol) by lipases in organic solvent, esterification patterns of triglyceride, diglyceride, and monoglyceride were monitored at various reaction times with 10 lipases. As a model study, tricaprin was synthesized from glycerol and capric acids (C 10:0 ) in isooctane. Lipases that were known to give nonspecific hydrolysis in aqueous solvent, such as lipase from Candida cylindracea, Lipase OF-360 (from C. rugosa), and Lipase MY (C. rugosa) showed nonspecific synthesis of tricaprin in organic solvent (Group I). There are two groups for esterifying triglycerides in organic solvent with 1,3-specific lipases: one consists of the lipases from Rhizomucor miehei, Pseudomonas aeruginosa (Lipase PS), and Chromobacterium viscosum (Lipase CV) (Group II), and another (Group III) is represented by Lipase AP (Aspergillus niger), Lipase FAP-15 (Rhizopus javanicus), and Lipase D (R. delemar). Although both groups showed 1,3-specific hydrolysis in aqueous solvent, Group III has stricter 1,3-specificity for the synthesis of tricaprin from dicaprin.

Enantiomeric Synthesis of (S)-2-Methylbutanoic Acid Methyl Ester, Apple Flavor, Using Lipases in Organic Solvent

“…These results mean that selection of the best lipase for hydrolysis, synthesis, or interesterification depends on the nature of substrate compounds (alcohols as acyl acceptors and acids as acyl donors) and their reaction mechanisms Kwon et al, 1996). Table 1 also shows that enantioselectivity of lipases was not affected by the lipase specificity (Kwon et al, 1997;Macrae, 1984). Synthetic activities and enantiomeric selectivities of (S)-MBE were determined in various solvents such as isooctane, octane, heptane, cyclohexane, and hexane to select the best solvent for this reaction, using three screened lipases, lipase IM 20, lipase AP, and lipase FAP-15.…”