Mono-thioesters and di-thioesters by lipase-catalyzed reactions of alpha,omega-alkanedithiols with palmitic acid or its methyl ester.
1- S-Mono-palmitoyl-hexanedithiol and 1- S-mono-palmitoyl-octanedithiol were prepared in high yield (80-90%) by solvent-free lipase-catalyzed thioesterification of palmitic acid with the corresponding alpha,omega-alkanedithiols in vacuo. Similarly, 1,6-di- S-palmitoyl-hexanedithiol and 1,8-di- S-palmitoyl-octanedithiol were prepared in moderate yield (50-60%) by solvent-free lipase-catalyzed thioesterification of palmitic acid with 1- S-Mono-palmitoyl-hexanedithiol and 1- S-mono-palmitoyl-octanedithiol, respectively. An immobilized lipase preparation from Rhizomucor miehei (Lipozyme RM IM) was more effective than a lipase B preparation from Candida antarctica (Novozym 435) or a lipase preparation from Thermomyces lanuginosus (Lipozyme TL IM). Lipase-catalyzed transthioesterifications of methyl palmitate with alpha,omega-alkanedithiols using the same enzymes were less effective than thioesterification for the preparation of the corresponding 1- S-mono-palmitoyl thioesters.
Weber
N
N
Institut für Lipidforschung, Bundesforschungsanstalt für Ernährung und Lebensmittel, Piusallee 68/76, 48147 Münster, Germany. niweber@uni-muenster.de
Klein
E
E
Vosmann
K
K
Mukherjee
K D
KD
D001203:Ascomycota; D002175:Candida; D004800:Enzymes, Immobilized; D004952:Esters / Q000138:chemical synthesis*; D005656:Fungal Proteins; D008049:Lipase / Q000737:chemistry* / Q000302:isolation & purification / Q000378:metabolism; D015394:Molecular Structure; D019308:Palmitic Acid / Q000737:chemistry*; D020103:Rhizomucor; D013438:Sulfhydryl Compounds / Q000138:chemical synthesis*
D004800:Enzymes, Immobilized; D004952:Esters; D005656:Fungal Proteins; D013438:Sulfhydryl Compounds; D019308:Palmitic Acid; C093666:Lipozyme; C093667:Novozyme 435; D008049:Lipase