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Folding-Induced Folding: The Assembly of Aromatic Amide and 1,2,3-Triazole Hybrid Helices
Alternative Title折叠诱导折叠: 芳酰胺-1,2,3-三氮唑杂化螺旋结构组装
Wu CF(吴春芳)1; Li ZM(李志明)1; Xu XN(徐晓娜)1; Zhao ZX(赵志雄)1; Zhao X(赵新)1; Wang RX(王任小)1; Li ZT(黎占亭)1
2014
Source PublicationChem.-Eur. J.
Volume20Issue:5Pages:1418-1426
AbstractFolding-induced folding for the construction of artificial hybrid helices from two different kinds of aromatic sequences is described. Linear compounds 1a, 1b, and 2, containing one aromatic amide trimer or pentamer and one or two aromatic 1,2,3-triazole tetramers, have been designed and synthesized. The trimeric and pentameric amide segments are driven by intramolecluar N-H center dot center dot center dot F hydrogen bonding to adopt a folded or helical conformation, whereas the triazole segment is intrinsically disordered. In organic solvents of low polarity, the amide foldamer segment induces the attached triazole segment(s) to fold through intramolecular stacking, leading to the formation of hybrid helices. The helical conformation of these hybrid sequences has been confirmed by H-1 and F-19 NMR spectroscopy, UV/Vis spectroscopy, circular dichroism (CD) experiments, and theoretical calculations. It was found that the amide pentamer exhibits a stronger ability to induce the folding of the attached triazole segment(s) compared with that of the shorter trimer. Enantiomers (R)-3 and (S)-3, which contain an R-or S-(1-naphthyl) ethylamino group at the end of a tetraamide segment, have also been synthesized. CD experiments showed that introduction of a chiral group caused the whole framework to produce a strong helicity bias. Density-functional-theory calculations on (S)-3 suggested that this compound exists as a right-handed (P) helix.
Subject Area物理有机化学
DOI10.1002/chem.201304161
URL查看原文
Indexed BySCI
Language英语
Citation statistics
Document Type期刊论文
Identifierhttp://ir.sioc.ac.cn/handle/331003/39146
Collection物理有机化学研究室
Corresponding AuthorZhao X(赵新); Li ZT(黎占亭)
Affiliation1.中科院上海有机化学研究所
2.复旦大学
Recommended Citation
GB/T 7714
Wu CF,Li ZM,Xu XN,et al. Folding-Induced Folding: The Assembly of Aromatic Amide and 1,2,3-Triazole Hybrid Helices[J]. Chem.-Eur. J.,2014,20(5):1418-1426.
APA 吴春芳.,李志明.,徐晓娜.,赵志雄.,赵新.,...&黎占亭.(2014).Folding-Induced Folding: The Assembly of Aromatic Amide and 1,2,3-Triazole Hybrid Helices.Chem.-Eur. J.,20(5),1418-1426.
MLA 吴春芳,et al."Folding-Induced Folding: The Assembly of Aromatic Amide and 1,2,3-Triazole Hybrid Helices".Chem.-Eur. J. 20.5(2014):1418-1426.
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