Robust mixed 10/12 helices promoted by "alternating chirality" in a new family of C-linked carbo-β-peptides

被引:96
作者
Sharma, GVM
Reddy, KR
Krishna, PR
Sankar, AR
Narsimulu, K
Kumar, SK
Jayaprakash, P
Jagannadh, B
Kunwar, AC
机构
[1] Indian Inst Chem Technol, Discovery Lab, Div Organ Chem 3, Hyderabad 500007, Andhra Pradesh, India
[2] Indian Inst Chem Technol, NMR Grp, Hyderabad 500007, Andhra Pradesh, India
[3] Indian Inst Chem Technol, Mol Modeling Unit, Hyderabad 500007, Andhra Pradesh, India
关键词
D O I
10.1021/ja035752i
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The C-linked carbo-β-peptides, oligomers of a new class of C-linked carbo-β3-amino acids, have been shown to generate mixed 12/10 and 10/12 helices. The design involves use of alternating chirality" of the epimeric (at the amine center) monomers to control the stability of these helices. The observation of stable 12/10 helix in a tripeptide and 10/12 helix in a tetrapeptide is unprecedented. Copyright © 2003 American Chemical Society."
引用
收藏
页码:13670 / 13671
页数:2
相关论文
共 28 条
[1]   Residue-based control of helix shape in beta-peptide oligomers [J].
Appella, DH ;
Christianson, LA ;
Klein, DA ;
Powell, DR ;
Huang, XL ;
Barchi, JJ ;
Gellman, SH .
NATURE, 1997, 387 (6631) :381-384
[2]   beta-peptide foldamers: Robust Helix formation in a new family of beta-amino acid oligomers [J].
Appella, DH ;
Christianson, LA ;
Karle, IL ;
Powell, DR ;
Gellman, SH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (51) :13071-13072
[3]   Theoretical and experimental circular dichroic spectra of the novel helical foldamer poly[(1R,2R)-trans-2-aminocyclopentanecarboxylic acid] [J].
Applequist, J ;
Bode, KA ;
Appella, DH ;
Christianson, LA ;
Gellman, SH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (19) :4891-4892
[4]   Sugar amino acids and their uses in designing bioactive molecules [J].
Chakraborty, TK ;
Ghosh, S ;
Jayaprakash, S .
CURRENT MEDICINAL CHEMISTRY, 2002, 9 (04) :421-435
[5]   β-peptides:: From structure to function [J].
Cheng, RP ;
Gellman, SH ;
DeGrado, WF .
CHEMICAL REVIEWS, 2001, 101 (10) :3219-3232
[6]  
Davis AP, 1999, ANGEW CHEM INT EDIT, V38, P2978
[7]   The twists and turns of β-peptides [J].
DeGrado, WF ;
Schneider, JP ;
Hamuro, Y .
JOURNAL OF PEPTIDE RESEARCH, 1999, 54 (03) :206-217
[8]   Glycobiology: Toward understanding the function of sugars [J].
Dwek, RA .
CHEMICAL REVIEWS, 1996, 96 (02) :683-720
[9]  
Gademann K, 1999, CURR MED CHEM, V6, P905
[10]   Foldamers: A manifesto [J].
Gellman, SH .
ACCOUNTS OF CHEMICAL RESEARCH, 1998, 31 (04) :173-180