Journal of Organic Chemistry 2004-03-19

Synthesis and conformational studies of novel cyclic peptides constrained into a 3 10 helical structure by a heterochiral D-pro-L-pro dipeptide template.

I Nageshwara Rao, Anima Boruah, S Kiran Kumar, A C Kunwar, A Sivalakshmi Devi, K Vyas, Krishnan Ravikumar, Javed Iqbal

Index: J. Org. Chem. 69 , 2181, (2004)

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Abstract

An acyclic tripeptide based on a heterochiral D-pro-L-pro template shows a propensity to exist as a 3(10) helical conformation and can be cyclized, via ring-closing metathesis, to the corresponding cyclic tetrapeptides without disrupting the helical conformations in CDCl(3) as well as in DMSO-d(6) solutions. The detailed conformational studies were carried out by using NMR spectroscopy, X-ray crystallography, molecular dynamic simulations, and circular dichroism spectroscopy.