Quick Search:

uzh logo
Browse by:
bullet
bullet
bullet
bullet

Zurich Open Repository and Archive 

Permanent URL to this publication: http://dx.doi.org/10.5167/uzh-51287

Stamm, S; Heimgartner, H (2006). Introduction of the Aib-Pro unit into peptides by means of the ‘azirine/oxazolone method’ on solid phase. Tetrahedron, 62(41):9671-9680.

[img]Published Version
PDF - Registered users only
390Kb
[img]
Preview
Accepted Version
PDF
181Kb

Abstract

A method for the direct introduction of Aib-Pro into peptides on solid phase was developed. The Aib-Pro unit was introduced by means of the ‘azirine/oxazolone method’ using allyl N-(2,2-dimethyl-2H-azirin-3-yl)-L-prolinate as the synthon. After the reaction of the resin-bound amino or peptide acid with allyl N-(2,2-dimethyl-2H-azirin-3-yl)-L-prolinate, the allyl protecting group of the resulting extended peptide could be removed by a mild Pd0-promoted procedure. Cleavage of the peptide from the resin was performed with UV light at 352 nm and yielded C-terminal protected peptides. The method found a successful application in the syntheses of different Aib-Pro containing peptaibol segments. Furthermore, a protected derivative of the peptide antibiotic Trichovirin I 1B was prepared by segment condensation.

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Institute of Organic Chemistry
DDC:540 Chemistry
Language:English
Date:2006
Deposited On:06 Dec 2011 08:46
Last Modified:19 Apr 2014 21:49
Publisher:Elsevier
ISSN:0040-4020
Funders:Swiss National Science Foundation , F. Hoffmann-La Roche AG, Basel
Publisher DOI:10.1016/j.tet.2006.07.082
Citations:Web of Science®. Times Cited: 14
Google Scholar™

Users (please log in): suggest update or correction for this item

Repository Staff Only: item control page