Synthesis of 5,6-dihydro-4H-1,3-thiazine containing peptide mimics from N-(3-hydroxypropyl)thioamides and epimerization studies
Data(s) |
2014
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Resumo |
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. |
Formato |
application/pdf |
Identificador |
http://eprints.iisc.ernet.in/49928/1/tet_hed_let_55-24_4731_2014.pdf 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. |
Publicador |
PERGAMON-ELSEVIER SCIENCE LTD |
Relação |
http://dx.doi.org/ 10.1016/j.tetlet.2014.06.084 http://eprints.iisc.ernet.in/49928/ |
Palavras-Chave | #Organic Chemistry |
Tipo |
Journal Article PeerReviewed |