Chemical ligation from O-acyl isopeptides via 8-and 11-membered cyclic transition states

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Abstract

Unprotected O-acylated serine and O-acylated threonine isopeptides have been synthesized, and their conversion to native tripeptides and tetrapeptides by O-to N-terminus transfer investigated. Ligations involving 8-and 11-membered cyclic transition states are shown experimentally and computationally to be more favorable than intermolecular cross-ligations.

Original languageEnglish (US)
Pages (from-to)91-106
Number of pages16
JournalArkivoc
Volume2014
Issue number4
DOIs
Publication statusPublished - Feb 10 2014

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Keywords

  • Benzotriazole
  • Ligation
  • Peptide
  • Serine
  • Threonine

ASJC Scopus subject areas

  • Organic Chemistry

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