Hydrogen bonding and isomerization in thioamide peptide derivatives

R. A. Shaw, E. Kollát, M. Hollósi, H. H. Mantsch

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Abstract

The conformations of fourteen thiopeptides in three solvents (acetonitrile, methylene chloride, DMSO) are discussed as inferred by interpretation of the amide infrared absorptions. The spectra indicate that the enhanced acidity of the thioamide NH proton (and hence the stronger hydrogen-bonding donor potential) promotes the formation of C5 ring structures that are not often found in unsubstituted peptides, and strong C(S)NH → OC hydrogen bonds render both C, (γ-turn) and C10 (β-turn) structures more stable than their oxoamide counterparts. The ability of infrared spectra to discriminate among C5, C7, and C10 structures is evaluated and discussed.

Original languageEnglish
Pages (from-to)1399-1412
Number of pages14
JournalSpectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy
Volume51
Issue number8
DOIs
Publication statusPublished - Jul 1995

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Keywords

  • Hydrogen bond
  • Isomerism
  • Peptide
  • Thiopeptide

ASJC Scopus subject areas

  • Analytical Chemistry
  • Atomic and Molecular Physics, and Optics
  • Instrumentation
  • Spectroscopy

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