Stereochemical control in the structures of linear δ,α-hybrid tripeptides containing tetrahydrofuran amino acids

Chakraborty, Tushar Kanti ; Kumar, N. V. Suresh ; Roy, Saumya ; Dutta, Samit Kumar ; Kunwar, Ajit Chand ; Sridhar, Balasubramanian ; Singh, Harjinder (2011) Stereochemical control in the structures of linear δ,α-hybrid tripeptides containing tetrahydrofuran amino acids Journal of Physical Organic Chemistry, 24 (8). pp. 720-731. ISSN 0894-3230

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Official URL: http://onlinelibrary.wiley.com/doi/10.1002/poc.181...

Related URL: http://dx.doi.org/10.1002/poc.1818

Abstract

Structural and electronic properties of diastereomers of tetrahydrofuran amino acids (TAA) derived tripeptide, Boc-TAA-Leu-Val-OMe, are studied using density functional theory. Predicted secondary folding patterns with hydrogen bonded pseudocycles of different sizes in peptides containing (2R,5S)-cis-TAA and (2S,5R)-cis-TAA are confirmed by detailed NMR studies of both, and single crystal X-ray analysis of the former. A novel unusual folding pattern emanating from three-centered hydrogen bond is found in peptide with (2R,5S)-cis relationship. Stereochemical control on the orientation of interacting sites is substantiated by structural analysis of the peptides. Using natural bonding orbital and atoms in molecules analyses, charge transfer interactions are analyzed.

Item Type:Article
Source:Copyright of this article belongs to John Wiley and Sons.
Keywords:Peptides; Tetrahydrofuran Amino Acid; Three-centered Hydrogen Bond; Turns
ID Code:69570
Deposited On:14 Nov 2011 03:53
Last Modified:14 Nov 2011 03:53

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