Hybrid Sequences that Express both Aromatic Amide and α-Peptidic Folding Features.,ChemPlusChem

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Hybrid Sequences that Express both Aromatic Amide and α-Peptidic Folding Features.
ChemPlusChem ( IF 3.0 ) Pub Date : 2020-07-06 , DOI: 10.1002/cplu.202000416
Xiaobo Hu ₁ , Pradeep K Mandal ₂ , Brice Kauffmann ₃ , Ivan Huc _{1,

2}

Affiliation

Foldamers combining aliphatic and aromatic main‐chain units often produce atypical structures that cannot easily be accessed from purely aromatic or aliphatic sequences. We report solid‐state evidence that sequences comprising α‐amino acids and quinoline‐based monomers adopt conformations that combine the folding propensities of both components. Foldamers 2 and 3 having an XQQ repeat motif (X=α‐amino acid, Q=quinoline) were synthesized. Crystals of 2 (X=Phe, Q with an anionic side chain) obtained from water revealed an aromatic helix where amide groups belonging to the α‐amino acids created a hydrogen‐bond array typical of peptidic helices. Crystals of 3 (X=Ser, Q with a lipophilic side chain) obtained from organic solvents revealed a helix‐turn‐helix structure in which α‐amino acid side chains interfere with main‐chain hydrogen bonding. High sequence‐dependency of the conformation is typical of peptides but is shown here to include aromatic folding features.

中文翻译：

同时表达芳香酰胺和 α-肽折叠特征的混合序列。

结合脂肪族和芳香族主链单元的折叠体通常会产生非典型结构，这些结构不容易从纯芳香族或脂肪族序列中获得。我们报告了固态证据，表明包含 α-氨基酸和喹啉基单体的序列采用结合了两种成分折叠倾向的构象。合成了具有 XQQ 重复基序（X=α-氨基酸，Q=喹啉）的折叠体2和3 。从水中获得的2 （X=Phe，带有阴离子侧链的 Q）晶体显示出芳香族螺旋，其中属于 α-氨基酸的酰胺基团形成了肽螺旋典型的氢键阵列。从有机溶剂中获得的3 （X=Ser，带有亲脂侧链的 Q）晶体显示出螺旋-转角-螺旋结构，其中 α-氨基酸侧链干扰主链氢键。构象的高度序列依赖性是肽的典型特征，但此处显示包括芳香族折叠特征。

更新日期：2020-07-30

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