Issue 8, 1990

Structural versatility of peptides from Cα,α-disubstituted glycines. Preferred conformation of the Cα,α-dibenzylglycine residue

Abstract

The preferred conformation of the Cα,α-dibenzylglycine residue has been assessed in selected derivatives and small peptides by conformational energy computations, 1H NMR spectroscopy, and X-ray diffraction. Conformational energy computations on the Cα,α-dibenzylglycine monopeptide, Ac-Dbz-NHMe, strongly support the view that this Cα,α-symmetrically disubstituted residue is conformationally restricted and that its minimum energy conformation falls in the fully-extended (C5) region. The results of the theoretical analysis are in agreement with the solution and crystal-state structural propensity of Tfa-Dbz-Gly-DBH, Tfa-Dbz-L-Phe-OMe and its benzyl ester analogue, m-ClAc-Dbz-OH, Z-Gly-Dbz-Gly-OH and its t-butyl ester derivative. The implications for the use of the Dbz residue in designing conformationally constrained analogues of bioactive peptides are briefly discussed.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 2, 1990, 1481-1487

Structural versatility of peptides from Cα,α-disubstituted glycines. Preferred conformation of the Cα,α-dibenzylglycine residue

G. Valle, M. Crisma, G. M. Bonora, C. Toniolo, F. Lelj, V. Barone, F. Fraternali, P. M. Hardy, A. Langran-Goldsmith and H. L. S. Maia, J. Chem. Soc., Perkin Trans. 2, 1990, 1481 DOI: 10.1039/P29900001481

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Spotlight

Advertisements