A simple, unsaturated, E–Z photoisomerizable β‐amino acid, (Z)‐3‐aminoprop‐2‐enoic acid, has been introduced into peptide foldamers through a one‐pot chemical coupling, based on Pd/Cu‐catalyzed olefin oxidative amidation, between two peptide segments carrying, respectively, a ‐Gly‐NH₂ residue at the C‐terminus and an acryloyl group at the N‐terminus. Reversible conversion between the Z and E configurations of the 3‐aminoprop‐2‐enoic linkage was achieved photochemically. A crystallographic analysis on two model compounds shed light on the consequences, in terms of 3D structure and self‐association properties, brought about by the different configuration of the unsaturated linkage. As a proof of concept, E–Z photoisomerization of a 3‐aminoprop‐2‐enoic acid residue, inserted as the junction between two conformationally distinct peptide domains (one helical while the other β‐sheet promoter), allowed supramolecular self‐association to be reversibly turned on/off.

中文翻译：

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固有的可光开关的α/β肽对两种状态的Foldamers的作用。

基于Pd / Cu催化的烯烃氧化反应，通过单锅化学偶联将一种简单的，不饱和的，E - Z光异构化的β-氨基酸（Z）-3-氨基丙-2-烯酸引入肽折叠剂在两个肽段之间的酰胺化反应，分别在C端带有一个Gly-NH ₂残基和在N端带有一个丙烯酰基。Z和E之间的可逆转换3-氨基丙-2-烯键的构型是通过光化学方法实现的。对两种模型化合物的晶体学分析揭示了由不饱和键的不同构型带来的后果，包括3D结构和自缔合特性。作为概念的证明，作为3个氨基丙-2-烯酸残基的E – Z光异构化，插入两个构象不同的肽结构域之间（一个螺旋形，另一个β-折叠启动子），允许超分子自缔合。可逆地打开/关闭。