Highly efficient preparation of sphingoid bases from glucosylceramides by chemoenzymatic method

作者：Gowda Siddabasave B Gowda; Usuki Seigo; Hammam Mostafa A S; Murai Yuta; Igarashi Yasuyuki; Monde Kenji^*

来源：The Journal of Lipid Research, 2016, 57(2): 325-331.

DOI：10.1194/jlr.D065268

• sphingolipids
• chemoenzymatic synthesis
• ceramide glucoside
• enzymology
• mass spectrometry

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 beta-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.

• 出版日期2016-2