Synthesis and Conformational Studies of Dipeptides Constrained by Disubstituted 3-(Aminoethoxy)propionic Acid Linkers

Reddy, D. Srinivasa ; Vander Velde, David ; Aubé, Jeffrey (2004) Synthesis and Conformational Studies of Dipeptides Constrained by Disubstituted 3-(Aminoethoxy)propionic Acid Linkers Journal of Organic Chemistry, 69 (5). pp. 1716-1719. ISSN 0022-3263

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Official URL: http://doi.org/10.1021/jo035683q

Related URL: http://dx.doi.org/10.1021/jo035683q

Abstract

A series of cyclic compounds with dimethyl-substituted 3-(aminoethoxy)propionic acid linkers have been prepared as potential beta-turn mimics. The desired linkers were prepared from disubstituted pyrones, which were coupled with dipeptides and then subjected to macrocyclization using diethylcyanophosphonate to furnish cyclic compounds 1-5. Conformational analysis was carried out using NMR and X-ray crystallography. All of the five cyclic compounds were found to exist in type I or type II beta-turn conformations.

Item Type:Article
Source:Copyright of this article belongs to American Chemical Society
ID Code:122024
Deposited On:27 Jul 2021 10:25
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