Direct aqueous synthesis of non-protected glycosyl sulfoxides; weak inhibitory activity against glycosidases. (2nd September 2015)

• Record Type: Journal Article
• Authors: Alexander, Stewart R.; Watson, Andrew J.A.; Fairbanks, Antony J.
• Is Part Of: Carbohydrate research. Volume 413(2015)
• Page Start: 123
• Page End: 128
• Publication Date: 2015-09-02
• Subjects: Glycosyl sulfoxide -- Thioglycoside -- Oxidation -- Biomimetic catalysis -- Glycosidase inhibition; Carbohydrates -- Periodicals; Chemistry, Organic -- Periodicals; Biochemistry -- Periodicals; Carbohydrates -- Periodicals; Chimie organique -- Périodiques; Glucides -- Périodiques; Biochemistry; Carbohydrates; Chemistry, Organic; Periodicals; Electronic journals; 507.78
• DOI: 10.1016/j.carres.2015.06.003
• Languages: English
• ISSNs: 0008-6215

Abstract

Abstract: A flavinium catalyst, in conjunction with hydrogen peroxide as stoichiometric oxidant, allowed the aqueous conversion of non-protected thioglycosides into the corresponding glycosyl sulfoxides. These glycosyl sulfoxides displayed only very weak inhibitory activity against corresponding glycosidases. Graphical abstract: Highlights: Oxidation of thioglycosides to glycosyl sulfoxides using a flavinium biomimetic catalyst. The use of hydrogen peroxide as the stoichiometric oxidant. 'Green' oxidation of non-protected thioglycosides in water. Inhibitory activity of three glycosyl sulfoxides against corresponding glycosidases.