文章基本信息

标题：Highly efficient preparation of sphingoid bases from glucosylceramides by chemoenzymatic method
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作者：Siddabasave Gowda B. Gowda ; Seigo Usuki ; Mostafa A. S. Hammam 等
期刊名称：JLR Papers In Press
印刷版ISSN：0022-2275
电子版ISSN：1539-7262
出版年度：2016
卷号：57
期号：2
页码：325-331
DOI：10.1194/jlr.D065268
语种：English
出版社：American Society for Biochemistry and Molecular Biology
摘要：Sphingoid base derivatives have attracted increasing attention as promising chemotherapeutic candidates against lifestyle diseases such as diabetes and cancer. Natural sphingoid bases can be a potential resource instead of those derived by time-consuming total organic synthesis. In particular, glucosylceramides (GlcCers) in food plants are enriched sources of sphingoid bases, differing from those of animals. Several chemical methodologies to transform GlcCers to sphingoid bases have already investigated; however, these conventional methods using acid or alkaline hydrolysis are not efficient due to poor reaction yield, producing complex by-products and resulting in separation problems. In this study, an extremely efficient and practical chemoenzymatic transformation method has been developed using microwave-enhanced butanolysis of GlcCers and a large amount of readily available almond β-glucosidase for its deglycosylation reaction of lysoGlcCers. The method is superior to conventional acid/base hydrolysis methods in its rapidity and its reaction cleanness (no isomerization, no rearrangement) with excellent overall yield.
关键词：sphingolipids ; chemoenzymatic synthesis ; ceramide glucoside ; enzymology ; mass spectrometry