title: Highly efficient preparation of sphingoid bases from glucosylceramides by chemoenzymatic method.
abstract: 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.
authors.affiliation: Graduate School of Life Science, Frontier Research Center for Post Genome Science and Technology, Faculty of Advanced Life Science, Hokkaido University, Hokkaido, Sapporo, Japan 001-0021.
authors.forename: Siddabasave Gowda B
authors.initials: SG
authors.lastname: Gowda
authors.affiliation: Laboratory of Biomembrane and Biofunctional Chemistry, Frontier Research Center for Post Genome Science and Technology, Faculty of Advanced Life Science, Hokkaido University, Hokkaido, Sapporo, Japan 001-0021.
authors.forename: Seigo
authors.initials: S
authors.lastname: Usuki
authors.affiliation: Laboratory of Chemical Biology, Frontier Research Center for Post Genome Science and Technology, Faculty of Advanced Life Science, Hokkaido University, Hokkaido, Sapporo, Japan 001-0021.
authors.forename: Mostafa A S
authors.initials: MA
authors.lastname: Hammam
authors.affiliation: Laboratory of Chemical Biology, Frontier Research Center for Post Genome Science and Technology, Faculty of Advanced Life Science, Hokkaido University, Hokkaido, Sapporo, Japan 001-0021.
authors.forename: Yuta
authors.initials: Y
authors.lastname: Murai
authors.affiliation: Laboratory of Biomembrane and Biofunctional Chemistry, Frontier Research Center for Post Genome Science and Technology, Faculty of Advanced Life Science, Hokkaido University, Hokkaido, Sapporo, Japan 001-0021.
authors.forename: Yasuyuki
authors.initials: Y
authors.lastname: Igarashi
authors.affiliation: Laboratory of Chemical Biology, Frontier Research Center for Post Genome Science and Technology, Faculty of Advanced Life Science, Hokkaido University, Hokkaido, Sapporo, Japan 001-0021 kmonde@sci.hokudai.ac.jp.
authors.forename: Kenji
authors.initials: K
authors.lastname: Monde
mesh_terms: D005963:Glucosylceramides / Q000737:chemistry*; D006801:Humans; D006868:Hydrolysis; D008872:Microwaves; D015394:Molecular Structure; D013107:Sphingolipids / Q000138:chemical synthesis / Q000737:chemistry*; D013110:Sphingosine / Q000138:chemical synthesis / Q000737:chemistry*
chemical_list: D005963:Glucosylceramides; D013107:Sphingolipids; D013110:Sphingosine
keywords: ceramide glucoside; chemoenzymatic synthesis; enzymology; mass spectrometry; sphingolipids