Induced helix of 2-(2-aminophenoxy)alkanoic acid oligomers as a δ-peptidomimetic foldamer
Induced helix of 2-(2-aminophenoxy)alkanoic acid oligomers as a δ-peptidomimetic foldamer
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DOI：
10.1016/j.tetlet.2008.05.003
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发表时间：
2008-07-07
影响因子：
1.8
通讯作者：
Ogura, Katsuyuki
中科院分区：
文献类型：
--
作者：
Akazome, Motohiro;Ishii, Yuichi;Ogura, Katsuyuki
以2-(2-氨基苯氧基)烷酸为原料，通过低聚反应合成了模拟多肽的2-氨基苯氧基烷酸。对四聚体的单晶分析表明，该四聚体为2(1)-螺旋二级结构，由氢键和芳环的卷曲堆积稳定。N-末端(R)-2-(2-硝基苯氧基)丙酰胺部分的单一手性碳的引入诱导了2-氨基二苯氧基乙酸低聚物的M-螺旋性。溶液态圆二色谱表明，所得到的螺旋诱导了显著的Cotton效应。用红外光谱和核磁共振光谱对其二级结构进行了进一步表征。(C)2008爱思唯尔有限公司。保留所有权利。
Peptidomimetic foldamers were synthesized by oligomerizing derivatives of the delta-amino acid analogue, 2-(2-aminophenoxy)alkanoic acid. Single-crystal analysis of the tetramer reveals a 2(1)-helical secondary structure stabilized by hydrogen bonding and the coiled stacking of aromatic rings. The M-helicity of 2-aminoplienoxyacetic acid oligomers was induced by the incorporation of only a single chiral carbon of the N-terminal (R)-2-(2-nitrophenoxy)propionamide moiety. The solution state CD spectra demonstrated that the resulting helix induced a substantial Cotton effect. The secondary structure was further characterized by IR and NMR spectroscopy. (c) 2008 Elsevier Ltd. All rights reserved.