<journal article>
Linkage-Editing Pseudo-Glycans: A Reductive α-Fluorovinyl-C-Glycosylation Strategy to Create Glycan Analogs with Altered Biological Activities

Creator
Language
Publisher
Date
Source Title
Vol
Issue
First Page
Last Page
Publication Type
Access Rights
Date of Available
Related DOI
Abstract The acetal (O-glycoside) bonds of glycans and glycoconjugates are chemically and biologically vulnerable, and therefore C-glycosides are of interest as more stable analogs. We hypothesized that, if th...e O-glycoside linkage plays a vital role in glycan function, the biological activities of C-glycoside analogs would vary depending on their substituents. Based on this idea, we adopted a “linkage-editing strategy” for the creation of glycan analogs (pseudo-glycans). We designed three types of pseudo-glycans with CH2 and CHF linkages, which resemble the O-glycoside linkage in terms of bond lengths, angles, and bulkiness, and synthesized them efficiently by means of fluorovinyl C-glycosylation and selective hydrogenation reactions. Application of this strategy to isomaltose (IM), an inducer of amylase expression, and α-GalCer, which activates iNKT cells, resulted in the discovery of CH2-IM, which shows increased amylase production ability, and CHF-α-GalCer, which shows activity opposite that of native α-GalCer, serving as an antagonist of iNKT cells.show more

Hide fulltext details.

Published Date:2025.01.24 pdf 1.38 MB    

Details

PISSN
EISSN
NCID
Record ID
Subject Terms
Type
Funding Information
Created Date 2024.05.21
Modified Date 2024.05.21

People who viewed this item also viewed