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.
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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.
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|Item Type:||Journal Article, refereed, original work|
|Communities & Collections:||07 Faculty of Science > Department of Chemistry|
|Dewey Decimal Classification:||540 Chemistry|
|Deposited On:||06 Dec 2011 07:46|
|Last Modified:||11 Jul 2014 00:15|
|Funders:||Swiss National Science Foundation , F. Hoffmann-La Roche AG, Basel|
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