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A Solution to Chemical Pseudaminylation via Development of a Bimodal Glycosyl Donor to Enable Highly Stereocontrolled α- and β-Glycosylation

preprint
submitted on 26.02.2019 and posted on 27.02.2019 by Ruohan Wei, Han Liu, Arthur Tang, Richard Payne, Xuechen Li
Bacterial pseudaminic acids (Pse) are present on the surface of many pathogenic bacteria. Herein, we report a robust methodology for the stereocontrolled chemical glycosylation of pseudaminic acid to afford both α- (axial) and β- (equatorial) glycosides reliably with complete stereoselectivity, using a common glycosyl donor (7N-Cbz/5N-azido Pse thioglycoside) simply by changing the reaction conditions (DCM-DMF, -40 oC and DCM/MeCN, -78 oC, respectively). Examples of such bimodal selectivity are both sparse and highly sought-after in carbohydrate chemistry. This method enables efficient access to pseudaminylated molecules, which will open up various opportunities in chemical glycobiology research of bacterial pseudaminic acids and carbohydrate-based antibacterial vaccine development.

Funding

C5026-16G, AoE/P-705/16 University Grants Council of Hong Kong

History

Email Address of Submitting Author

xuechenl@hku.hk

Institution

The University of Hong Kong

Country

Hong Kong

ORCID For Submitting Author

0000-0001-5465-7727

Declaration of Conflict of Interest

No conflict of interest

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