Demethylative Alkylation of Methionine Residue by Employing the Sulfonium as the Key Intermediate

Methionine (Met) offers a valuable handle to achieve peptide chemical modification owing to its unique thioether functional group. In contrast with cysteine, the site-selective functionalization of the hydrophobic and redox-sensitive thioether motif on peptides is still challenging, and strategies f...

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Bibliographic Details
Published inOrganic letters Vol. 23; no. 21; pp. 8543 - 8548
Main Authors Hu, Qi-Long, Liu, Jia-Tian, Li, Jian, Ge, Yang, Song, Zhendong, Chan, Albert S. C, Xiong, Xiao-Feng
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 05.11.2021
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
FUNCTIONALIZATION
POLYPEPTIDES
PEPTIDES
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Summary:Methionine (Met) offers a valuable handle to achieve peptide chemical modification owing to its unique thioether functional group. In contrast with cysteine, the site-selective functionalization of the hydrophobic and redox-sensitive thioether motif on peptides is still challenging, and strategies for diversification on the Met residue are rarely disclosed. Herein we report a transition-metal-free and redox-neutral approach for Met diversification with substrate diversity, which could be applied to synthesize cyclic peptides.
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content type line 23
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.1c03241