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(4R)- and (4S)-Azidoprolines : conformation directing amino acids and sites for functionalization

Erdmann, Roman and Kümin, Michael and Wennemers, Helma. (2009) (4R)- and (4S)-Azidoprolines : conformation directing amino acids and sites for functionalization. Chimia, 63 (4). pp. 197-200.

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Official URL: http://edoc.unibas.ch/dok/A5262567

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Abstract

An ‘azido gauche effect’ determines the conformation of (4S)- and (4R)-azidoproline (Azp) derivatives and affects the s-cis:s-trans conformer ratio of Xaa-Azp bonds. The article summarizes our research on the con- formational analysis of monomers as well as oligomers derived from (4S)Azp and (4R)Azp. We show that (4S)Azp and (4R)Azp can be used to tune the stability of the polyproline II (PPII) helix. In addition we demonstrate that Azp containing oligoprolines are attractive molecular scaffolds with a well-defined helical conformation that can be readily further functionalized using e.g. click chemistry.
Faculties and Departments:05 Faculty of Science > Departement Chemie > Former Organization Units Chemistry > Bioorganische Chemie (Wennemers)
UniBasel Contributors:Wennemers, Helma
Item Type:Article, refereed
Article Subtype:Research Article
Bibsysno:Link to catalogue
Publisher:Schweizerische Chemische Gesellschaft
ISSN:0009-4293
Note:Publication type according to Uni Basel Research Database: Journal article
Language:English
Identification Number:
Last Modified:20 Nov 2017 09:28
Deposited On:22 Mar 2012 14:07

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