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Improved solid-phase synthesis and study of arylopeptoids with conformation-directing side chains |
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| Authors: | Thomas Hjelmgaard Sophie Faure Emiliana De Santis Dan Staerk Bruce D Alexander Alison A Edwards Claude Taillefumier John Nielsen |
| Institution: | 1. Department of Basic Sciences and Environment, University of Copenhagen, Thorvaldsensvej 40, 1871 Frederiksberg C, Denmark;2. CNRS, UMR6504, Laboratoire SEESIB, 63177 Aubière Cedex, France;3. Clermont Université, Université Blaise Pascal, BP 10448, 63000 Clermont-Ferrand, France;4. Medway School of Pharmacy, Universities of Kent and Greenwich at Medway, Central Avenue, Chatham Maritime, Kent ME4 4TB, United Kingdom;5. School of Science, University of Greenwich, Central Avenue, Chatham Maritime, Kent ME4 4TB, United Kingdom |
| Abstract: | The development of an improved methodology for iterative solid-phase synthesis of para- and meta-arylopeptoids (oligomeric N-substituted aminomethyl benzamides) using benzoyl chloride building blocks is described. This methodology has enabled the synthesis of arylopeptoids with tert-butyl and phenyl side chains, which allows for complete control over the amide conformation: the tert-butyl results in a 100% cis amide conformation while the phenyl side chain results in a 100% trans amide conformation. The method has furthermore enabled the first synthesis and preliminary conformational studies of arylopeptoids bearing (S)-N-(1-phenylethyl) side chains. |
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