Lie Ken Jie M S, Syed-Rahmatullah M S
Department of Chemistry, University of Hong Kong, Hong Kong.
Lipids. 1995 Nov;30(11):995-9. doi: 10.1007/BF02536283.
Incubation of a 1-pyrroline ester [viz. methyl 8-(5-hexyl-1-pyrroline-2-yl)octanoate, 1] with bakers' yeast (Saccharomyces cerevisiae) gave the corresponding free fatty acid (1a, 52%). The C = N bond of the 1-pyrroline was not reduced by the yeast. Complete hydrolysis of compound 1 was successful using lipase of Candida cylindracea (CCL) or Lipolase (Rhizomucor miehei) under stirred or ultrasound condition. Fatty esters containing a pyrrolidine [viz. methyl 8-(cis/trans-5-hexyl-pyrrolidine-2-)octanoate, 2] or N-methyl pyrrolidine [viz. methyl 8-(cis-5-hexyl-N-methyl-pyrrolidine-2-)octanoate, 3] system in the alkyl chain were not hydrolyzed by either CCL or Lipolase, unless conducted in an ultrasonic bath. The hydrolytic activities of the enzymes appeared to be strongly affected by the stereochemistry of the N-heterocyclic ring system. Chemical hydrolysis of compounds 1-3 gave the corresponding fatty acid N-HCl salts.
将1-吡咯啉酯[即8-(5-己基-1-吡咯啉-2-基)辛酸甲酯，1]与面包酵母（酿酒酵母）一起孵育，得到相应的游离脂肪酸（1a，产率52%）。酵母未还原1-吡咯啉的C=N键。在搅拌或超声条件下，使用柱状假丝酵母脂肪酶（CCL）或米黑根毛霉脂肪酶（Lipolase）可成功实现化合物1的完全水解。含有吡咯烷[即8-(顺式/反式-5-己基-吡咯烷-2-)辛酸甲酯，2]或N-甲基吡咯烷[即8-(顺式-5-己基-N-甲基-吡咯烷-2-)辛酸甲酯，3]体系的脂肪酯，除非在超声浴中进行，否则CCL或Lipolase均不能将其水解。酶的水解活性似乎受N-杂环系统立体化学的强烈影响。化合物1-3的化学水解得到相应的脂肪酸N-HCl盐。
