ePrints@IIScePrints@IISc Home | About | Browse | Latest Additions | Advanced Search | Contact | Help

Structural studies of model peptides containing beta-, gamma- and delta-amino acids

Sengupta, Anindita and Aravinda, Subrayashastry and Shamala, Narayanaswamy and Raja, Muruga Poopathi K and Balaram, Padmanabhan (2006) Structural studies of model peptides containing beta-, gamma- and delta-amino acids. In: Organic & Biomolecular Chemistry, 4 (22). pp. 4214-4222.

[img] PDF
b609863k.pdf - Published Version
Restricted to Registered users only

Download (466Kb) | Request a copy
Official URL: http://www.rsc.org/publishing/journals/OB/article....

Abstract

The crystal structures of five model peptides Piv-Pro-Gly-NHMe (1), Piv-Pro-beta Gly-NHMe (2), Piv-Pro-beta Gly-OMe (3), Piv-Pro-delta Ava-OMe (4) and Boc-Pro-gamma Abu-OH (5) are described (Piv:pivaloyl; NHMe: N-methylamide; beta Gly:beta-glycine; OMe:O-methyl ester; delta Ava:delta-aminovaleric acid; gamma Abu:gamma-aminobutyric acid). A comparison of the structures of peptides 1 and 2 illustrates the dramatic consequences upon backbone homologation in short sequences. 1 adopts a type II beta-turn conformation in the solid state, while in 2, the molecule adopts an open conformation with the beta-residue being fully extended. Piv-Pro-beta Gly-OMe (3), which differs from 2 by replacement of the C-terminal NH group by an O-atom, adopts an almost identical molecular conformation and packing arrangement in the solid state. In peptide 4, the observed conformation resembles that determined for 2 and 3, with the delta Ava residue being fully extended. In peptide 5, the molecule undergoes a chain reversal, revealing a beta-turn mimetic structure stabilized by a C-H center dot center dot center dot O hydrogen bond.

Item Type: Journal Article
Additional Information: Copyright of this article belongs to Royal Society of Chemistry.
Department/Centre: Division of Biological Sciences > Molecular Biophysics Unit
Division of Physical & Mathematical Sciences > Physics
Date Deposited: 04 Aug 2010 08:59
Last Modified: 19 Sep 2010 06:12
URI: http://eprints.iisc.ernet.in/id/eprint/30823

Actions (login required)

View Item View Item