Synthesis and Solid State Conformation of Tetrapeptide Amides Containing two Aib and two (aMe)Phe Residues – Use of Enantiomerically Pure 2‐Benzyl‐2‐methyl‐2H‐azirin‐3‐amines as (aMe)Phe‐Synthons,Chemistry & Biodiversity

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Synthesis and Solid State Conformation of Tetrapeptide Amides Containing two Aib and two (aMe)Phe Residues – Use of Enantiomerically Pure 2‐Benzyl‐2‐methyl‐2H‐azirin‐3‐amines as (aMe)Phe‐Synthons
Chemistry & Biodiversity ( IF 2.3 ) Pub Date : 2020-06-17 , DOI: 10.1002/cbdv.202000246
Christoph B Bucher ₁ , Anthony Linden ₂ , Heinz Heimgartner ₂

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A series of tetrapeptide amides containing two aminoisobutyric acids (Aib) and two α‐methylphenylalanine ((αMe)Phe) units were prepared through the ‘azirine/oxazolone method’. New 2‐benzyl‐2‐methyl‐2H‐azirin‐3‐amines have been used for the selective introduction of (S)‐ and (R)‐(αMe)Phe, respectively. The solid‐state conformations of five tetrapeptide amides were determined by X‐ray crystallography. In all cases, two β‐turns stabilize 310‐helical conformations and it was confirmed that, in contrast to proteinogenic amino acids, the configuration of (αMe)Phe does not determine the screw sense of the helix.

中文翻译：

含有两个 Aib 和两个 (aMe)Phe 残基的四肽酰胺的合成和固态构象 – 使用对映体纯的 2-Benzyl-2-methyl-2H-azirin-3-胺作为 (aMe)Phe-Synthons

通过“氮丙啶/恶唑酮法”制备了一系列含有两个氨基异丁酸 (Aib) 和两个 α-甲基苯丙氨酸 ((αMe)Phe) 单元的四肽酰胺。新的 2-benzyl-2-methyl-2H-azirin-3-amines 分别用于选择性引入 (S)- 和 (R)-(αMe)Phe。通过 X 射线晶体学确定了五种四肽酰胺的固态构象。在所有情况下，两个 β 转角稳定了 310 螺旋构象，并且证实，与蛋白氨基酸相比，(αMe)Phe 的构型并不能决定螺旋的螺旋结构。

更新日期：2020-06-17

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