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Published on: October 4, 2017
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The Development of DNA-Compatible S-Glycosyl Transformations.
Qingyi Zhao1,2, Yandan Bao1,2, Dawen Niu3,4
1School of Chinese Materia Medica, Nanjing University of Chinese Medicine, 138 Xianlin Road, Nanjing 210023, China.
Organic Letters
|June 26, 2023
Summary
We developed two DNA-compatible S-glycosyl transformations for creating glycosylated DNA-encoded libraries (DELs). A photoinduced method using allyl sugar sulfones shows broad compatibility and efficiency for synthesizing novel glycosyl DELs.
Area of Science:
- Organic Chemistry
- Chemical Biology
- Medicinal Chemistry
Background:
- DNA-encoded libraries (DELs) are powerful tools for drug discovery.
- Efficient methods for synthesizing diverse DELs are crucial.
- Incorporating carbohydrates into DELs can expand chemical space and therapeutic potential.
Purpose of the Study:
- To develop novel S-glycosyl transformations compatible with DNA-encoded library construction.
- To explore efficient methods for conjugating sugars to DNA-linked molecules.
- To create glycosylated DELs for drug discovery and delivery system applications.
Main Methods:
- Investigated 2-chloro-1,3-dimethylimidazolidinium chloride (DMC)-mediated S-glycosylation with unprotected sugars.
- Developed a photoinduced, radical-based S-glycosyl transformation using allyl sugar sulfones.
- Performed conjugations on DNA-linked compounds under green light irradiation.
Main Results:
- The DMC-mediated method had limited substrate scope for DEL construction.
- The photoinduced method demonstrated excellent functional group compatibility with sugars and peptides.
- Achieved good to excellent conversions for DNA-linked glycosyl derivatives using the photoinduced approach.
Conclusions:
- The photoinduced S-glycosyl transformation is a pioneering, DNA-compatible method for synthesizing glycosyl DELs.
- This methodology provides a valuable tool for preparing diverse glycosylated compounds.
- Enables new avenues for exploring sugar-incorporated delivery systems and therapeutic agents.
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