Intramolecular Hydrogen Bonding in Depsipeptides Containing Endo-3,6- Tricyclo[6.2.1.02,7]undeca-4,9-diene-3,6-endo-diol
Authors: Axt M.1; Oulyadi H.1; Pannecoucke X.1; Quirion J-C.1; Pohlmann A.R.1; Uberti Costa V.E.m.i.l.i.o.1
Source: Current Drug Discovery Technologies, Volume 1, Number 2, June 2004 , pp. 155-164(10)
Publisher: Bentham Science Publishers
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Abstract:
A variety of endo-3,6-tricyclo[6.2.1.02,7]undeca-4,9-diene-3,6-endo-diol depsipeptide or bis-amino acid derivatives containing the same parallel strands were synthesised and examined for conformational preferences by NMR. The study indicates that this novel class of constrained peptides displays
-turn-like and -sheet-like conformations. Evidences are supported by observation of the rates of proton-deuterium exchange, nuclear Overhauser effects and further by dynamic simulations, semi-empirical and ab initio calculations. The chemical shifts were measured in CDCl3 and CDCl3 with 15% DMSO-d6 solutions. It was carried out a van't Hoff analysis, which is in agreement with the theoretical studies. In chloroform-d, for the derivatives 3-6 the hydrogen-bonded species are enthalpically preferred but entropically disfavoured.
Keywords: Polycyclic compounds; peptide; conformational analysis
Document Type: Review article
DOI: 10.2174/1570163043335081
Affiliations: 1: Instituto de Quimica, Universidade Federal do Rio Grande do Sul. CP 15003. Av. Bento Gonçalves, 9500 - Porto Alegre 91.501-970 - RS-Brasil;
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