Helical Peptide-Foldamers Having a Chiral Five-Membered Ring Amino Acid with Two Azido Functional Groups
Helical Peptide-Foldamers Having a Chiral Five-Membered Ring Amino Acid with Two Azido Functional Groups
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具有带有两个叠氮基官能团的手性五元环氨基酸的螺旋肽折叠体
DOI：
10.1021/jo501493x
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发表时间：
2014
期刊：
影响因子：
--
通讯作者：
and Masakazu Tanaka
中科院分区：
文献类型：
--
作者：
Makoto Oba;Hiroomi Takazaki;Naomi Kawabe;Mitsunobu Doi;Yosuke Demizu;Masaaki Kurihara;Hiromu Kawakubo;Masanobu Nagano;Hiroshi Suemune;and Masakazu Tanaka
设计并合成了一个手性五元环α，α-二取代α-氨基酸（R，R）-Ac 5cdN 3，它含有两个叠氮基官能团。环状氨基酸（R，R）-Ac 5cdN 3可以有效地转化为具有不同的两个1，2，3-三唑官能团的环状氨基酸。制备了（R，R）-Ac 5cdN 3纯手性肽（直至六肽）和（R，R）-Ac 5cdN 3-含I-Leu基的肽，并完成了它们的叠氮官能团向三唑基团的转化。通过红外吸收光谱、圆二色谱、核磁共振氢谱和X射线晶体学分析，研究了“点击反应”前后低聚物的构象变化以及氨基酸残基的叠氮效应。环状氨基酸（R，R）-Ac 5cdN 3可作为螺旋构象控制残基，并在其寡肽中具有多功能化位点。
A chiral five-membered ring α,α-disubstituted α-amino acid (R,R)-Ac5cdN3having two azido functional groups has been designed and synthesized. The cyclic amino acid (R,R)-Ac5cdN3could be efficiently converted into several cyclic amino acids with various two 1,2,3-triazole functional groups. (R,R)-Ac5cdN3homochiral peptides (up to hexapeptide) and (R,R)-Ac5cdN3-containingl-Leu-based peptides were prepared, and their conversion of azido functional groups into triazole groups was completed. The preferred conformation of oligomers, before and after the “click reaction”, together with the azidogaucheeffect of amino acid residues were studied using FT-IR absorption, CD,1H NMR, and X-ray crystallographic analysis. The cyclic amino acid (R,R)-Ac5cdN3could be used as a helical conformation controlling residue and also has a versatile functionalizing site in its oligopeptides.