β-Strand mimetics: formation of bend-strands in oligomers of enantiomeric β-amino acids

被引:30
作者
Chandrasekhar, Srivari [1 ]
Sudhakar, Ambadi [1 ]
Kiran, Marelli Udaya [2 ]
Babu, Bathini Nagendra [1 ]
Jagadeesh, Bharatam [2 ]
机构
[1] Indian Inst Chem Technol, Organ Div 1, Hyderabad 500007, Andhra Pradesh, India
[2] Indian Inst Chem Technol, Ctr Nucl Magnet Resonance, Hyderabad 500007, Andhra Pradesh, India
关键词
beta-Strands; Oligomers; Amino acid; Hydrogen bonding;
D O I
10.1016/j.tetlet.2008.10.031
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Oligomers comprising of enantiomeric cis-oxo-beta-norbornene amino acid [2R,3S] and [2S,3R] residues at alternate positions were synthesized and characterized by extensive NMR and MD Studies, which showed robust bend-strand secondary structures. (C) 2008 Elsevier Ltd. All rights reserved.
引用
收藏
页码:7368 / 7371
页数:4
相关论文
共 30 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]   Radio-analytical determination of the coating efficiency of cyclic RGD peptides [J].
Auernheimer, Jorg ;
Haubner, Roland ;
Schottelius, Margret ;
Wester, Hans-Jurgen ;
Kessler, Horst .
HELVETICA CHIMICA ACTA, 2006, 89 (05) :833-840
[3]   NATURAL PROTEIN PROTEINASE-INHIBITORS AND THEIR INTERACTION WITH PROTEINASES [J].
BODE, W ;
HUBER, R .
EUROPEAN JOURNAL OF BIOCHEMISTRY, 1992, 204 (02) :433-451
[4]   3-DIMENSIONAL STRUCTURE OF THE HUMAN CLASS-II HISTOCOMPATIBILITY ANTIGEN HLA-DR1 [J].
BROWN, JH ;
JARDETZKY, TS ;
GORGA, JC ;
STERN, LJ ;
URBAN, RG ;
STROMINGER, JL ;
WILEY, DC .
NATURE, 1993, 364 (6432) :33-39
[5]   Oligomers of cis-β-norbornene amino acid:: Formation of β-strand mimetics [J].
Chandrasekhar, S ;
Babu, BN ;
Prabhakar, A ;
Sudhakar, A ;
Reddy, MS ;
Kiran, MU ;
Jagadeesh, B .
CHEMICAL COMMUNICATIONS, 2006, (14) :1548-1550
[6]   Expanding the conformational pool of cis-β-sugar amino acid:: Accommodation of β-hGly motif in robust 14-helix [J].
Chandrasekhar, S ;
Reddy, MS ;
Babu, BN ;
Jagadeesh, B ;
Prabhakar, A ;
Jagannadh, B .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (27) :9664-9665
[7]   Formation of a stable 14-helix in short oligomers of furanoid cis-β-sugar-amino acid' [J].
Chandrasekhar, S ;
Reddy, MS ;
Jagadeesh, B ;
Prabhakar, A ;
Rao, MHVR ;
Jagannadh, B .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (42) :13586-13587
[8]   β-peptides:: From structure to function [J].
Cheng, RP ;
Gellman, SH ;
DeGrado, WF .
CHEMICAL REVIEWS, 2001, 101 (10) :3219-3232
[9]   Conformational selection of inhibitors and substrates by proteolytic enzymes: Implications for drug design and polypeptide processing [J].
Fairlie, DP ;
Tyndall, JDA ;
Reid, RC ;
Wong, AK ;
Abbenante, G ;
Scanlon, MJ ;
March, DR ;
Bergman, DA ;
Chai, CLL ;
Burkett, BA .
JOURNAL OF MEDICINAL CHEMISTRY, 2000, 43 (07) :1271-1281
[10]   Application of alicyclic β-amino acids in peptide chemistry [J].
Fülöp, F ;
Martinek, TA ;
Tóth, GK .
CHEMICAL SOCIETY REVIEWS, 2006, 35 (04) :323-334