Absolute handedness control of oligoamide double helices by chiral oxazolylaniline induction

被引：9
|
作者：
Yang, Ling [1 ]
Ma, Chunmiao [1 ]
Kauffmann, Brice [2 ]
Li, Dongyao [1 ]
Gan, Quan [1 ]
机构：
[1] Huazhong Univ Sci & Technol, Sch Chem & Chem Engn, Hubei Key Lab Bioinorgan Chem & Mat Med, Wuhan 430074, Peoples R China
[2] Univ Bordeaux, CNRS, Inst Europeen Chim & Biol, IECB,UMS3033,US001,INSERM, 2 Rue Robert Escarpit, F-33600 Pessac, France
来源：
ORGANIC & BIOMOLECULAR CHEMISTRY | 2020年 / 18卷 / 34期
基金：
中国国家自然科学基金;
关键词：
FOLDAMERS; POLYMERS; AMPLIFICATION; SENSE; RECOGNITION; ASSEMBLIES; MOLECULES; SINGLE;
D O I：
10.1039/d0ob01503b
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Aromatic oligoamide double helices bearing a chiral oxazolylaniline moiety at the C-terminus were synthesized and their helix handedness was completely controlled (de > 99%). The absolute helix sense and the de values were evaluated by using H-1 NMR, X-ray crystallography, and circular dichroism (CD). Using crystal structure analysis, the high efficiency of helix handedness induction was attributed to the close location of the asymmetric carbon center to the helix orbitsviaintramolecular hydrogen bonding. The CD experiments also showed that there is no loss of chiral induction either in the interconversion of single and double helices or by elongation of the sequences.
引用
收藏
页码：6643 / 6650
页数：8
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