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Crystal-structure analysis of cis-X-pro-containing peptidomimetics: understanding the steric interactions at cis X-pro amide bonds

Reddy, Damodara N and George, Gijo and Prabhakaran, Erode N (2013) Crystal-structure analysis of cis-X-pro-containing peptidomimetics: understanding the steric interactions at cis X-pro amide bonds. In: Angewandte Chemie International Edition, 52 (14). pp. 3935-3939.

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Official URL: http://dx.doi.org/10.1002/anie.201209517

Abstract

Catch the twist: The cis Piv-Pro conformer (Piv=pivaloyl) of peptides is no longer inaccessible. Any cis X-Pro tertiary-amide-bond conformer can be stabilized in crystals of peptides by accommodating the unavoidable distortion of the dihedral angle of the peptide bond to the carbonyl group of the Pro residue (see picture), in this case through ni−1→πi* interactions. Steric clashes were not observed in the cis Piv-Pro rotamers studied.

Item Type: Journal Article
Additional Information: Copyright of this article belongs to John Wiley and Sons, Inc.
Keywords: Bond Distortions; Cis; Trans Isomerism; Conformation Analysis; Peptidomimetics; Steric Interactions
Department/Centre: Division of Chemical Sciences > Organic Chemistry
Depositing User: Id for Latest eprints
Date Deposited: 04 Jun 2013 11:58
Last Modified: 04 Jun 2013 11:58
URI: http://eprints.iisc.ac.in/id/eprint/46530

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