Controlling Helix Handedness in Water-Soluble Quinoline Oligoamide Foldamers

被引：32
|
作者：
Dawson, Simon J. [1 ,2 ]
Meszaros, Adam [3 ]
Petho, Lilla [3 ]
Colombo, Cinzia [1 ,2 ]
Csekei, Marton [3 ]
Kotschy, Andras [3 ]
Huc, Ivan [1 ,2 ]
机构：
[1] Univ Bordeaux, CBMN, UMR 5248, Inst Europeen Chim & Biol, F-33607 Pessac, France
[2] CNRS, UMR5248, CBMN, Inst Europeen Chim & Biol, F-33607 Pessac, France
[3] Servier Res Inst Med Chem, H-1031 Budapest, Hungary
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2014年 / 2014卷 / 20期
基金：
欧洲研究理事会;
关键词：
Chirality; Helical structures; Conformation analysis; Foldamers; Oligoamides; VIBRATIONAL CIRCULAR-DICHROISM; PROTEIN-PROTEIN INTERACTIONS; SOLID-PHASE SYNTHESIS; N; N'-LINKED OLIGOUREAS; SECONDARY STRUCTURE; ABSOLUTE HELICITY; CHIRAL INDUCTION; NMR; SPECTROSCOPY; PEPTIDES;
D O I：
10.1002/ejoc.201402247
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
For biological applications, the control of the helix handedness of water-soluble quinoline-based oligoamide foldamers has been investigated by the installation of chiral end groups at either the C or N terminus. This has resulted in the development of monomer units capable of unequivocally inducing helical sense without impacting the aqueous solubility. Furthermore, we showed that very slow helix handedness inversion in water can be exploited. The incorporation of a chiral moiety with no handedness-induction properties allows the chromatographic separation of P and M helices as diastereoisomers with kinetically locked handedness.
引用
收藏
页码：4265 / 4275
页数：11
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