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Site-selective incorporation of thioamide-linkages into a growing peptide


Lehmann, Jürg; Linden, Anthony; Heimgartner, Heinz (1999). Site-selective incorporation of thioamide-linkages into a growing peptide. Tetrahedron, 55:5359-5376.

Abstract

The use of endothiodipeptide anilides, which were obtained in high yields by a variation of the 'azirine/oxazolone method', for the synthesis of longer endothiopeptides is described. With this novel methodology, epimerically pure endothiopeptides with the thiocarbonyl group next to the bulky Aib were prepared in satisfactory yields.The structures of two endothiotripeptides and
one endothiotetrapeptide were established by single-crystal X-ray crystallography.

Abstract

The use of endothiodipeptide anilides, which were obtained in high yields by a variation of the 'azirine/oxazolone method', for the synthesis of longer endothiopeptides is described. With this novel methodology, epimerically pure endothiopeptides with the thiocarbonyl group next to the bulky Aib were prepared in satisfactory yields.The structures of two endothiotripeptides and
one endothiotetrapeptide were established by single-crystal X-ray crystallography.

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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:English
Date:1999
Deposited On:05 Nov 2013 16:33
Last Modified:05 Apr 2016 17:06
Publisher:Elsevier
ISSN:0040-4020
Funders:Swiss National Science Foundation, F. Hoffmann-La Roche AG, Basel
Publisher DOI:https://doi.org/10.1016/S0040-4020(99)00234-3

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