Novel 1→6- & 6→6-linked ester disaccharide analogs – synthesis and structural evaluation

Document Type

Poster

Department

Chemistry

Conference Title

251st American Chemical Society (ACS) National Meeting

Organization

American Chemical Society (ACS)

Location

San Diego, CA

Conference Dates

March 13-17, 2016

Date of Presentation

3-13-2016

Abstract

Carbohydrate mimetics have been an active area of drug discovery, especially with regard to their potential use as glycosidase inhibitors. The incorporation of uronic acids into oligosaccharides allows ester-linkages to other sugars. This general ‘ester disaccharide’ motif has previously found use in a “redox glycosylation” approach to stereoselective glycosydic linkage, as well as in the development of trehalose-based compounds for drug delivery matrices. Furthermore, non-methyl O-galacturonoyl esters have been implicated in natural products, such as pectins and xylans. However, the basic 1-O- and 6-O-glucuronoyl-D-glucopyranoses and their stereoisomers derived from other hexoses have until now not been synthesized and studied in depth. Here, we report the synthesis and structural study of 1→6- and 6→6-linked versions of these ester disaccharide analogs from readily accessible precursors. In addition, progress on the expansion of the employed synthetic methods to other sugars and derivatives thereof will be reported.

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