Improved solid-phase synthesis and study of arylopeptoids with conformation-directing side chains

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• 作者：Thomas Hjelmgaard^a ; ^{thhj@life.ku.dk} ; Sophie Faure^b ; ^c ; Emiliana De Santis^d ; Dan Staerk^a ; Bruce D. Alexander^e ; Alison A. Edwards^d ; Claude Taillefumier^b ; ^c ; ^{claude.taillefumier@univ-bpclermont.fr} ; John Nielsen^a
• 关键词：Foldamers ; Aromatic oligoamides ; Peptoids ; Solid-phase synthesis ; Conformational analysis
• 刊名：Tetrahedron
• 出版年：2012
• 期刊代码：107_00404020
• 类别：ch
• 出版时间：10 June, 2012
• 卷：68
• 期：23
• 页码：4444-4454
• 文件大小：674 K

摘要

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.