Induced helix of 2-(2-aminophenoxy)alkanoic acid oligomers as a δ-peptidomimetic foldamer

被引：20

作者：

Akazome, Motohiro ^{[1
]}

Ishii, Yuichi ^{[1
]}

Nireki, Tatsuya ^{[1
]}

Ogura, Katsuyuki ^{[1
]}

机构：

[1] Chiba Univ, Grad Sch Engn, Dept Appl Chem & Biotechnol, Inage Ku, Chiba 2638522, Japan

来源：

TETRAHEDRON LETTERS | 2008年 / 49卷 / 28期

关键词：

foldamers; delta-amino acid; helical structure; hydrogen bonding;

D O I：

10.1016/j.tetlet.2008.05.003

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：4430 / 4433

页数：4

共 52 条

[31] Aromatic δ-peptides:: design, synthesis and structural studies of helical, quinoline-derived oligoamide foldamers [J].