Synthesis of 5,6-dihydro-4H-1,3-thiazine containing peptide mimics from N-(3-hydroxypropyl)thioamides and epimerization studies

Tumminakatti, Shama and Reddy, Damodara N and Lakshmi, Aparna N and Prabhakaran, Erode N (2014) Synthesis of 5,6-dihydro-4H-1,3-thiazine containing peptide mimics from N-(3-hydroxypropyl)thioamides and epimerization studies. In: TETRAHEDRON LETTERS, 55 (34). pp. 4731-4735.

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Abstract

The first synthesis of 1,3-thiazine fused peptide mimics is described from N-(3-hydroxypropyl)thioamides under MsCl/NEt3 conditions. The method is amenable to oligopeptidomimics with polar and apolar side chains. Substantial epimerization occurs at chiral C(2) exo methines in non-Pro fused mimics even under neutral conditions. H-1 NMR and crystal structure analyses indicate that the Thi analogues primarily associate with each other through intermolecular hydrogen bonds, involving the nitrogen of 1,3-thiazine and the N-H of the fused residue, which may be the basis for enamination-racemization process in these peptide mimics. (C) 2014 Elsevier Ltd. All rights reserved.

Item Type:	Journal Article
Publication:	TETRAHEDRON LETTERS
Publisher:	PERGAMON-ELSEVIER SCIENCE LTD
Additional Information:	Copy right for this article belongs to the PERGAMON-ELSEVIER SCIENCE LTD, THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND
Keywords:	1,3-Thiazine; Peptidomimic; Epimerization; Thioamide; Lawesson's reagent
Department/Centre:	Division of Chemical Sciences > Organic Chemistry
Date Deposited:	24 Sep 2014 05:50
Last Modified:	24 Sep 2014 05:50
URI:	http://eprints.iisc.ac.in/id/eprint/49928

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