Tug‐of‐War in a Dynamic Helical Peptide: Solvent‐Induced Helix‐Helix Transition of a Lactam‐Bridged Peptide Composed of Point‐ and Axial Chiralities Remote from Each Other,Chemistry - An Asian Journal

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Tug‐of‐War in a Dynamic Helical Peptide: Solvent‐Induced Helix‐Helix Transition of a Lactam‐Bridged Peptide Composed of Point‐ and Axial Chiralities Remote from Each Other
Chemistry - An Asian Journal ( IF 3.5 ) Pub Date : 2018-09-04 , DOI: 10.1002/asia.201801111
Akio Urushima ₁ , Naoki Ousaka ₁ , Eiji Yashima ₁

Affiliation

The dynamic axial chirality of oligopeptide‐bound 2,2′‐bipyridine (bpy) residues can be remote‐controlled and diastereoselectively locked. A right‐handed (P)‐3₁₀‐helix is first induced in the dynamic helical oligopeptide by an l‐valine (l‐Val) far from the bpy moiety and the induced axial bpy chirality is diastereoselectively dioxidized. The resulting l‐Val‐containing linear oligopeptides at the 3,3′‐positions retain their (P)‐3₁₀‐helices independent of the axial chirality (aR or aS) of the N‐terminal N,N′‐dioxide‐bpy unit, while a lactam‐bridged dynamic helical oligopeptide exhibits a unique solvent‐induced helix‐helix transition as a result of competitive helix‐inducing biases between the l‐Val and (aR) or (aS)‐N,N′‐dioxide‐bpy residues remote from each other along the entire oligopeptide chain in a tug‐of‐war like manner.

中文翻译：

动态螺旋肽中的拖轮：由相互远离的点和轴手性组成的内酰胺桥联肽的溶剂诱导的螺旋-螺旋转变

寡肽结合的2,2'-联吡啶（bpy）残基的动态轴向手性可以远程控制和非对映选择性锁定。首先在动态螺旋寡肽中由离bpy部分较远的l-缬氨酸（l- Val）诱导出右旋（P）-3 ₁₀螺旋，并且诱导的轴向bpy手性被非对映选择性地二氧化。所得的在3,3'-位含有l -Val的线性寡肽保留其（P）-3 ₁₀螺旋，与N-末端N，N'的轴向手性（A R或S）无关-二氧化物-bpy单元，而内酰胺桥联的动态螺旋寡肽表现出独特的溶剂诱导的螺旋-螺旋转变，这是由于l- Val与（a R）或（a S）-N之间竞争性的螺旋诱导偏差，N'彼此沿着整个寡肽链二氧化物联吡啶残基远程在拖船的军舰等的方式。

更新日期：2018-09-04

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