Vibrational spectroscopy of C7 H-bonded structures: Studies on peptide and glycopeptide models

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Abstract

This paper reports FTIR spectroscopic studies on cyclic peptides and N-glycosylated bridged cyclic peptides {cyclo[Gly-Pro-Xxx(GlcNAc)-Gly-δ-Ava], Xxx = Ash, Gin} with possible H-bonded β- (C10) and/or γ-turn (C7) structures, as well as on model compounds which are capable of forming C7 intramolecular hydrogen bonds (IHBs), such as Ac-Gly-NHMe and N-acetyl-2-acetamido-2-deoxy-β-D-glucopyranosylamine (GlcNAc-NHAc). In certain cases, the assignment of the characteristic amide I frequencies to the acceptor amide carbonyls was assisted by 13C isotope labelling or by additional structural information inferred from NMR measurements. The influence of solvent (trifluoroethanol and dimethyl sulphoxide) on the stability of C10 and C7 IHBs is also discussed.

Original languageEnglish
Pages (from-to)207-211
Number of pages5
JournalJournal of Molecular Structure
Volume408-409
DOIs
Publication statusPublished - Jun 1 1997

Keywords

  • C-labelling
  • FTIR
  • H-bonding
  • β-Turn
  • γ-Turn

ASJC Scopus subject areas

  • Analytical Chemistry
  • Spectroscopy
  • Organic Chemistry
  • Inorganic Chemistry

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