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Novel N-(2,2-Dimethyl-2H-azirin-3-yl)-L-prolinates as Aib-Pro Synthons


Stamm, S; Heimgartner, H (2006). Novel N-(2,2-Dimethyl-2H-azirin-3-yl)-L-prolinates as Aib-Pro Synthons. Helvetica Chimica Acta, 89(9):1841-1855.

Abstract

The syntheses of phenacyl N-(2,2-dimethyl-2H-azirin-3-yl)-L-prolinate and allyl N-(2,2-dimethyl-2H-azirin-3-yl)-L-prolinate are reported. Reactions of these 2H-azirin-3-amine derivatives with Z-protected amino acids have shown them to be suitable synthons for the Aib-Pro unit in peptide synthesis. After incorporation into the peptide by means of the 'azirine/oxazolone method', the C-termini of the resulting peptides were deprotected selectively with Zn in AcOH or by a mild Pd0-promoted procedure, respectively.

Abstract

The syntheses of phenacyl N-(2,2-dimethyl-2H-azirin-3-yl)-L-prolinate and allyl N-(2,2-dimethyl-2H-azirin-3-yl)-L-prolinate are reported. Reactions of these 2H-azirin-3-amine derivatives with Z-protected amino acids have shown them to be suitable synthons for the Aib-Pro unit in peptide synthesis. After incorporation into the peptide by means of the 'azirine/oxazolone method', the C-termini of the resulting peptides were deprotected selectively with Zn in AcOH or by a mild Pd0-promoted procedure, respectively.

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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:2006
Deposited On:06 Dec 2011 07:43
Last Modified:05 Apr 2016 15:07
Publisher:Verlag Helvetica Chimica Acta
ISSN:0018-019X
Publisher DOI:https://doi.org/10.1002/hlca.200690178

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