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Zipper-featured delta-peptide foldamers driven by donor-acceptor interaction. Design, synthesis, and characterization

文献类型:期刊论文

作者Zhao X(赵新) ; Jia MX(贾木欣) ; Jiang XK(蒋锡夔) ; Wu LZ(吴骊珠) ; Li ZT(黎占亭) ; Chen GJ(陈光巨)
刊名J. Org. Chem.
出版日期2004
卷号69期号:2页码:270-279
ISSN号0022-3263
其他题名协同供体-受体相互作用驱动的拉链结构特征的?-肽折叠体
通讯作者黎占亭 ; 陈光巨
英文摘要Donor-acceptor interaction between electron-rich 1,5-dioxynaphthalene (DAN) and electron-deficient pyromellitic diimide (PDI) has been utilized to induce the formation of a new kind of zipper-featured delta-peptide foldamers. Seven L-ornithine-based delta-peptides 1a-g, in which one to three DNA and PDI units are incorporated to the two ends of the peptide backbones, respectively, have been designed and prepared by the standard liquid-phase synthetic method. H-1 NMR, LTV-vis, and fluorescent quenching studies reveal that all the delta-peptides adopt folding conformations in nonpolar chloroform and polar DMF as a result of intramolecular donor-acceptor interaction between the DAN and PDI units. The folding states become more compact for the peptide skeletons possessing more donor-acceptor interacting sites. Variable-temperature LTV-vis experiments indicate that, although the folding is a dynamic process, the folding state can remain even at 150degreesC in DMF. Circular dichroism (CD) investigations reveal that the new generation of delta-peptides have similar folding patterns. A zipper-featured folding motif has been proposed for the new generation of delta-peptide foldamers. Molecular modeling has generated two most stable folding states for the longest 6-peptide 1g, with an energy difference of 26.80 kcal/mol.
学科主题物理有机化学
收录类别SCI
原文出处http://dx.doi.org/10.1021/jo035149i
语种英语
WOS记录号WOS:000188496300005
公开日期2013-01-16
源URL[http://202.127.28.38/handle/331003/12664]  
专题上海有机化学研究所_物理有机化学研究室
推荐引用方式
GB/T 7714
Zhao X,Jia MX,Jiang XK,et al. Zipper-featured delta-peptide foldamers driven by donor-acceptor interaction. Design, synthesis, and characterization[J]. J. Org. Chem.,2004,69(2):270-279.
APA 赵新,贾木欣,蒋锡夔,吴骊珠,黎占亭,&陈光巨.(2004).Zipper-featured delta-peptide foldamers driven by donor-acceptor interaction. Design, synthesis, and characterization.J. Org. Chem.,69(2),270-279.
MLA 赵新,et al."Zipper-featured delta-peptide foldamers driven by donor-acceptor interaction. Design, synthesis, and characterization".J. Org. Chem. 69.2(2004):270-279.

入库方式: OAI收割

来源:上海有机化学研究所

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