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(4R)- and (4S)-Azidoprolines : conformation directing amino acids and sites for functionalization
JournalArticle (Originalarbeit in einer wissenschaftlichen Zeitschrift)
 
ID 178635
Author(s) Erdmann, Roman; Kümin, Michael; Wennemers, Helma
Author(s) at UniBasel Wennemers, Helma
Year 2009
Title (4R)- and (4S)-Azidoprolines : conformation directing amino acids and sites for functionalization
Journal Chimia
Volume 63
Number 4
Pages / Article-Number 197-200
Keywords Azidoproline, Collagen, Gauche effect, Peptides, Polyproline II helix
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.
Publisher Schweizerische Chemische Gesellschaft
ISSN/ISBN 0009-4293
edoc-URL http://edoc.unibas.ch/dok/A5262567
Full Text on edoc Available
Digital Object Identifier DOI 10.2533/chimia.2009.197
ISI-Number WOS:000265917600005
Document type (ISI) Article
 
   

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