Second-generation sugar-assisted ligation: A method for the synthesis of cysteine-containing glycopeptides

Simon Ficht, Richard J. Payne, Ashraf Brik, Chi Huey Wong

Research output: Contribution to journalArticlepeer-review

70 Scopus citations

Abstract

(Chemical Equation Presented) Sweet ligations: A second-generation sugar-assisted ligation is described that incorporates a sugar moiety with an ester-linked thiol auxiliary. Efficient auxiliary removal leads to native glycopeptides without the use of protecting groups. Extended glycopeptides also facilitate efficient ligation reactions by this method, therefore making it possible to scan a target sequence until a synthetically viable ligation junction is found.

Original languageEnglish
Pages (from-to)5975-5979
Number of pages5
JournalAngewandte Chemie - International Edition
Volume46
Issue number31
DOIs
StatePublished - 15 Aug 2007

Keywords

  • Acyl transfer
  • Auxiliaries
  • Carbohydrates
  • Glycopeptides
  • Ligation

ASJC Scopus subject areas

  • Catalysis
  • General Chemistry

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