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Synthesis of the Endothiopeptide BOC-Trp-Ile-Ala-Aib-lle-Val[CSNH]Aib-Leu-Aib-Pro-OMe by a Variation of the 'Azirine/Oxazolone Method'


Lehmann, Jürg; Linden, Anthony; Heimgartner, Heinz (1998). Synthesis of the Endothiopeptide BOC-Trp-Ile-Ala-Aib-lle-Val[CSNH]Aib-Leu-Aib-Pro-OMe by a Variation of the 'Azirine/Oxazolone Method'. Tetrahedron, 54(30):8721-8736.

Abstract

The synthesisof the decaendothiopeptide BOC-Trp-Ile-Ala-Aib-lle-Val[CSNH]Aib-Leu-Aib-Pro-OMe is described. The introduction of the thioamide group next to the bulky Aib occurred via a variation of the 'azirine/oxazolone method' without epimerisation. The structure of the decaendothiopeptide was etablished by single-crystal X-ray crystallography, thereby two types of helices could be observed.

Abstract

The synthesisof the decaendothiopeptide BOC-Trp-Ile-Ala-Aib-lle-Val[CSNH]Aib-Leu-Aib-Pro-OMe is described. The introduction of the thioamide group next to the bulky Aib occurred via a variation of the 'azirine/oxazolone method' without epimerisation. The structure of the decaendothiopeptide was etablished by single-crystal X-ray crystallography, thereby two types of helices could be observed.

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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:1998
Deposited On:12 Nov 2013 14:08
Last Modified:05 Apr 2016 17:07
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(98)00506-7

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