Journal
TETRAHEDRON
Volume 68, Issue 23, Pages 4444-4454Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2011.12.049
Keywords
Foldamers; Aromatic oligoamides; Peptoids; Solid-phase synthesis; Conformational analysis
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Funding
- Villum Kann Rasmussen Foundation
- Carlsberg Foundation [2009_01_0745, 2010_01_0518]
- Lundbeck Foundation
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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. (C) 2011 Elsevier Ltd. All rights reserved.
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