Vibrational Circular Dichroism of Proline-Containing Oligopeptides

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Abstract:

Vibrational circular dichroism (VCD) and infrared absorption spectra in the amide A region of blocked oligopeptides containing proline have been obtained in apolar organic solvents in order to clarify the characteristic VCD for the intramolecularly hydrogen-bonded NH stretching involved in the turn structures of peptide chains as well as the intermolecularly hydrogen-bonded NH stretching in associated molecules. The γ-turn with the intramolecularly hydrogen-bonded C7 conformation exhibits a characteristic positive VCD band at about 3330 cm-1 in dilute solutions of Piv-Pro-NHMe and Ac-Pro-NHMe. The intramolecularly hydrogen-bonded NH stretching in the type II β-turn with C10 conformation gives rise to a positive VCD band at 3345 cm-1 for Piv-Pro-Gly-NHMe. The Gly NH group of Piv-Pro-Gly-OMe and Ac-Pro-Gly-OMe in dilute solutions assumes C7C5 conformation stabilized by a bifurcated three-center intramolecular hydrogen bond and exhibits a positive VCD band near 3300 cm-1 at a lower frequency than the intermolecularly hydrogen-bonded band. All the peptides studied give a characteristic negative-positive bisignate couplet from the high wavenumber side for the intermolecularly hydrogen-bonded NH stretching band at high concentrations.

Keywords: Conformation of peptides; Hydrogen bonding; Infrared absorption; Molecular association; Proline-containing oligopeptides; Vibrational circular dichroism

Document Type: Research Article

DOI: http://dx.doi.org/10.1366/0003702963905817

Affiliations: 1: Institute for Protein Research, Osaka University, Suita, Osaka 565, Japan; present address: National Institute of Sericultural and Entomological Science (NISES), 1-2 Ohwashi, Tsukuba Science City, Ibaraki 305, Japan 2: Faculty of Textile Science and Technology, Shinshu University, Ueda, Nagano 386, Japan 3: Institute for Protein Research, Osaka University, Suita, Osaka 565, Japan

Publication date: May 1, 1996

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