Facile Diastereoseparation of Glycosyl Sulfoxides by Chiral Stationary Phase

Tohru Taniguchi; Mai Asahata; Akihito Nasu; Yukatsu Shichibu; Katsuaki Konishi; Kenji Monde

doi:10.1002/chir.22610

Facile Diastereoseparation of Glycosyl Sulfoxides by Chiral Stationary Phase

Chirality. 2016 Jul;28(7):534-9. doi: 10.1002/chir.22610. Epub 2016 Jun 14.

Authors

Tohru Taniguchi¹, Mai Asahata¹, Akihito Nasu¹, Yukatsu Shichibu², Katsuaki Konishi², Kenji Monde¹

Affiliations

¹ Faculty of Advanced Life Science, Frontier Research Center for Post-Genome Science and Technology, Hokkaido University, Sapporo, Japan.
² Faculty of Environmental Earth Science, Hokkaido University, Sapporo, Japan.

PMID: 27296702
DOI: 10.1002/chir.22610

Abstract

Separation of the diastereomers of glycosyl sulfoxides differing in the sulfur chirality has been difficult. This article presents a fast and scalable method for their diastereoseparation using a chiral stationary phase. The usefulness of this method was demonstrated in a 500-mg scale separation within 20 min, and in the separation of trisaccharyl sulfoxide diastereomers. Chirality 28:534-539, 2016. © 2016 Wiley Periodicals, Inc.

Keywords: Kahne glycosidation; carbohydrate; chiral HPLC; sulfur chirality.

Publication types

Research Support, Non-U.S. Gov't