Spectroscopic detection of pseudo-turns in homodetic cyclic penta- and hexapeptides comprising beta-homoproline

Malesevic M, Majer Z, Vass E, Huber T, Strijowski U, Hollosi M, Sewald N (2006)
INTERNATIONAL JOURNAL OF PEPTIDE RESEARCH AND THERAPEUTICS 12(2): 165-177.

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Abstract
beta-Amino acids with side chains at C-2 and/or at C-3 are of growing interest in drug design, as they may induce astonishing and unusual peptide conformations. Therefore it is of eminent importance to gather information on the consequences of beta-amino acid incorporation on the three-dimensional structure of a peptide. This paper describes the synthesis and conformational analysis of cyclic penta- and hexapeptides comprising either (S)-Pro or (S)-beta-Hpro. The conformational influence of the beta-homoproline building block was analyzed by the combined application of CD, FT-IR and NMR. While the CD spectra of the proline containing peptides indicate the presence of inverse gamma-turns and beta II-turns, the CD spectra of the beta-homoamino acid analogs are dominated by an unprecedented negative band near 205 nm associated with a pseudo-beta-turn (Psi beta) or pseudo-gamma-turn (Psi gamma). These results were confirmed by FT-IR spectroscopy, which also indicates the formation of two internal hydrogen bonds in the cyclic peptides containing the beta-homoproline. The conformations of the beta-homoproline containing pentapeptides were additionally determined by NMR in combination with MD simulations in two different solvents. The conformation in trifluoroethanol (TFE) is characterized by a bifurcated hydrogen bond stabilizing a pseudo-gamma-turn with beta-homoproline in the central position, nested with a pseudo-beta-turn with beta-homoproline in the i + l position. The combined CD/FT-IR studies clearly show that the replacement of proline by beta-homoproline gives rise to a more flexible peptide backbone, and CD spectroscopy hints towards the presence of pseudo-beta- or pseudo-gamma-turns.
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Malesevic M, Majer Z, Vass E, et al. Spectroscopic detection of pseudo-turns in homodetic cyclic penta- and hexapeptides comprising beta-homoproline. INTERNATIONAL JOURNAL OF PEPTIDE RESEARCH AND THERAPEUTICS. 2006;12(2):165-177.
Malesevic, M., Majer, Z., Vass, E., Huber, T., Strijowski, U., Hollosi, M., & Sewald, N. (2006). Spectroscopic detection of pseudo-turns in homodetic cyclic penta- and hexapeptides comprising beta-homoproline. INTERNATIONAL JOURNAL OF PEPTIDE RESEARCH AND THERAPEUTICS, 12(2), 165-177.
Malesevic, M., Majer, Z., Vass, E., Huber, T., Strijowski, U., Hollosi, M., and Sewald, N. (2006). Spectroscopic detection of pseudo-turns in homodetic cyclic penta- and hexapeptides comprising beta-homoproline. INTERNATIONAL JOURNAL OF PEPTIDE RESEARCH AND THERAPEUTICS 12, 165-177.
Malesevic, M., et al., 2006. Spectroscopic detection of pseudo-turns in homodetic cyclic penta- and hexapeptides comprising beta-homoproline. INTERNATIONAL JOURNAL OF PEPTIDE RESEARCH AND THERAPEUTICS, 12(2), p 165-177.
M. Malesevic, et al., “Spectroscopic detection of pseudo-turns in homodetic cyclic penta- and hexapeptides comprising beta-homoproline”, INTERNATIONAL JOURNAL OF PEPTIDE RESEARCH AND THERAPEUTICS, vol. 12, 2006, pp. 165-177.
Malesevic, M., Majer, Z., Vass, E., Huber, T., Strijowski, U., Hollosi, M., Sewald, N.: Spectroscopic detection of pseudo-turns in homodetic cyclic penta- and hexapeptides comprising beta-homoproline. INTERNATIONAL JOURNAL OF PEPTIDE RESEARCH AND THERAPEUTICS. 12, 165-177 (2006).
Malesevic, Miroslav, Majer, Zsuzsanna, Vass, Elemer, Huber, Thomas, Strijowski, Ulf, Hollosi, Miklos, and Sewald, Norbert. “Spectroscopic detection of pseudo-turns in homodetic cyclic penta- and hexapeptides comprising beta-homoproline”. INTERNATIONAL JOURNAL OF PEPTIDE RESEARCH AND THERAPEUTICS 12.2 (2006): 165-177.
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