通过脂肪酶催化α,ω-链烷二硫醇与棕榈酸或其甲酯反应制备单硫酯和二硫酯。
Mono-thioesters and di-thioesters by lipase-catalyzed reactions of alpha,omega-alkanedithiols with palmitic acid or its methyl ester.
作者信息
Weber N, Klein E, Vosmann K, Mukherjee K D
机构信息
Institut für Lipidforschung, Bundesforschungsanstalt für Ernährung und Lebensmittel, Piusallee 68/76, 48147 Münster, Germany.
出版信息
Appl Microbiol Biotechnol. 2004 Jun;64(6):800-5. doi: 10.1007/s00253-004-1604-8. Epub 2004 Mar 27.
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.
1 - S - 单棕榈酰己二硫醇和1 - S - 单棕榈酰辛二硫醇通过在真空中用相应的α,ω - 链烷二硫醇对棕榈酸进行无溶剂脂肪酶催化的硫酯ification反应以高产率（80 - 90%）制备。类似地，1,6 - 二 - S - 棕榈酰己二硫醇和1,8 - 二 - S - 棕榈酰辛二硫醇分别通过用1 - S - 单棕榈酰己二硫醇和1 - S - 单棕榈酰辛二硫醇对棕榈酸进行无溶剂脂肪酶催化的硫酯ification反应以中等产率（50 - 60%）制备。来自米黑根毛霉的固定化脂肪酶制剂（Lipozyme RM IM）比来自南极假丝酵母的脂肪酶B制剂（Novozym 435）或来自嗜热栖热菌的脂肪酶制剂（Lipozyme TL IM）更有效。使用相同酶对棕榈酸甲酯与α,ω - 链烷二硫醇进行脂肪酶催化的转硫酯ification反应在制备相应的1 - S - 单棕榈酰硫酯方面不如硫酯ification有效。
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