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ChemRxiv-XLi.pdf (1.07 MB)
A Solution to Chemical Pseudaminylation via Development of a Bimodal Glycosyl Donor to Enable Highly Stereocontrolled α- and β-Glycosylation
Preprints are manuscripts made publicly available before they have been submitted for formal peer review and publication. They might contain new research findings or data. Preprints can be a draft or final version of an author's research but must not have been accepted for publication at the time of submission.
submitted on 26.02.2019 and posted on 27.02.2019by 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.