Non-classical -saccharide linkage of dehydroalanine: synthesis of -glycoamino acids and -glycopeptides.

Chem Commun (Camb)

Research Unit of Peptide Science, Chinese Academy of Medical Sciences, 2019RU066, Lanzhou 730000, China.

Published: March 2023

AI Article Synopsis

  • A new method is introduced for linking sugars using a non-classical -saccharide linkage through radical additions to Michael acceptors.
  • C(sp)-S cleaved glycosyl thianthrenium salts are created to serve as effective glycosyl radical agents in this process.
  • This technique allows for the efficient synthesis of β-glycosyl substituted unnatural amino acids and enables modifications of peptides later in the synthesis process.

Article Abstract

Herein, a non-classical -saccharide linkage is reported a C5 radical of pentose or C6 radical of hexose addition to Michael acceptors. C(sp)-S cleaved glycosyl thianthrenium salts are developed as the glycosyl radical agents. The reaction provides an efficient toolkit to synthesize β-glycosyl substituted unnatural amino acids as well as for the late-stage -saccharide modification of peptides.

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Source
http://dx.doi.org/10.1039/d2cc06653jDOI Listing

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