A Diversity-Oriented Strategy for Chemoenzymatic Synthesis of Glycosphingolipids and Related Derivatives

A diversity-oriented strategy combining enzymatic glycan assembly and on-site lipid remodeling via chemoselective cross-metathesis and N-acylation was developed for glycosphingolipid (GSL) synthesis starting from a common, simple glycoside. The strategy was verified with a series of natural GSLs and...

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Bibliographic Details
Published in:Organic letters 2020-11, Vol.22 (21), p.8245-8249
Main Authors: Li, Qingjiang, Jaiswal, Mohit, Rohokale, Rajendra S, Guo, Zhongwu
Format: Article
Language:English
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Summary:A diversity-oriented strategy combining enzymatic glycan assembly and on-site lipid remodeling via chemoselective cross-metathesis and N-acylation was developed for glycosphingolipid (GSL) synthesis starting from a common, simple glycoside. The strategy was verified with a series of natural GSLs and GSL derivatives and showed several advantages. Most notably, it enabled two-way diversification of the glycan and lipid, including introduction of designed molecular tags, to provide functionalized GSLs useful for biological studies and applications.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.0c02847