Carbohydrate–DNA Conjugation Enabled by Glycosyl Radicals Generated from Glycosyl Sulfinates

Herein, we report a method that enables the synthesis of carbohydrate–DNA conjugates by radical addition. Key to the success is the use of readily available, bench-stable, and unprotected glycosyl sulfinates as precursors to glycosyl radicals. The redox neutral reaction proceeds under mild and simpl...

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Bibliographic Details
Published in:Organic letters 2024-04, Vol.26 (14), p.2686-2690
Main Authors: Zeng, Hongxin, Li, Yanjing, Wu, Rongfeng, Liu, Daqi, Zhang, Yang, Xu, Shiyang, Niu, Dawen
Format: Article
Language:English
Subjects:
DNA
Glycosides
Oxidation-Reduction
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Summary:Herein, we report a method that enables the synthesis of carbohydrate–DNA conjugates by radical addition. Key to the success is the use of readily available, bench-stable, and unprotected glycosyl sulfinates as precursors to glycosyl radicals. The redox neutral reaction proceeds under mild and simple conditions and tolerates a broad substrate scope. A small library of carbohydrate–DNA conjugates was prepared.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.3c00833