Abstract
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 α,ω-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 α,ω-alkanedithiols using the same enzymes were less effective than thioesterification for the preparation of the corresponding 1-S-mono-palmitoyl thioesters.
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Dedicated to Professor Dr Helmut K. Mangold, former Executive Director, Federal Centre for Lipid Research, Institute for Biochemistry and Technology, Münster, Germany, on the occasion of his 80th birthday on 19 June 2004
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Weber, N., Klein, E., Vosmann, K. et al. Mono-thioesters and di-thioesters by lipase-catalyzed reactions of α,ω-alkanedithiols with palmitic acid or its methyl ester. Appl Microbiol Biotechnol 64, 800–805 (2004). https://doi.org/10.1007/s00253-004-1604-8
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DOI: https://doi.org/10.1007/s00253-004-1604-8