Recent advances in the development of aryl-based foldamers

被引:303
作者
Saraogi, Ishu [1 ]
Hamilton, Andrew D. [1 ]
机构
[1] Yale Univ, Dept Chem, New Haven, CT 06511 USA
基金
美国国家卫生研究院;
关键词
DE-NOVO DESIGN; PHENYLENE ETHYNYLENE OLIGOMERS; ALPHA/BETA-PEPTIDE FOLDAMERS; HELICAL MOLECULAR STRANDS; AROMATIC AMIDE FOLDAMERS; SOLID-PHASE SYNTHESIS; AMINO-ACIDS; SECONDARY STRUCTURES; AQUEOUS-MEDIA; SIDE-CHAINS;
D O I
10.1039/b819597h
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
In recent years, significant effort has gone into making synthetic oligomers that can attain well-defined conformations analogous to the folding of biomolecules. The diversity of the structural building blocks ranges from peptidic and other aliphatic repeat units to aromatic ones, which do not have a natural counterpart. In this critical review, we will focus on the developments in aromatic foldamers in the last two years and their potential applications. This review will be of interest to people working on the structural and functional mimicry of biomolecules and will, we hope, stimulate further research into novel applications (149 references).
引用
收藏
页码:1726 / 1743
页数:18
相关论文
共 150 条
[1]   Facile synthesis of benzamides to mimic an α-helix [J].
Ahn, Jung-Mo ;
Han, Sun-Young .
TETRAHEDRON LETTERS, 2007, 48 (20) :3543-3547
[2]   Induced helix of 2-(2-aminophenoxy)alkanoic acid oligomers as a δ-peptidomimetic foldamer [J].
Akazome, Motohiro ;
Ishii, Yuichi ;
Nireki, Tatsuya ;
Ogura, Katsuyuki .
TETRAHEDRON LETTERS, 2008, 49 (28) :4430-4433
[3]   Nonpeptidic foldamers from amino acids: Synthesis and characterization of 1,3-substituted triazole oligomers [J].
Angelo, NG ;
Arora, PS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (49) :17134-17135
[4]   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
[5]   Control of helix formation in vinylogous γ-peptides by (E)- and (Z)-double bonds:: A way to ion channels and monomolecular nanotubes [J].
Baldauf, C ;
Günther, R ;
Hofmann, HJ .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (14) :5351-5361
[6]   Converting sequences of aromatic amino acid monomers into functional three-dimensional structures: Second-generation helical capsules [J].
Bao, Chunyan ;
Kauffmann, Brice ;
Gan, Quan ;
Srinivas, Kolupula ;
Jiang, Hua ;
Huc, Ivan .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (22) :4153-4156
[7]   Sheet-forming abiotic hetero foldamers [J].
Baruah, Pranjal K. ;
Sreedevi, Naduthottiyil K. ;
Majumdar, Baisakhi ;
Pasricha, Renu ;
Poddar, Pankaj ;
Gonnade, Rajesh ;
Ravindranathan, Sapna ;
Sanjayan, Gangadhar J. .
CHEMICAL COMMUNICATIONS, 2008, (06) :712-714
[8]   BINOL-based foldamers - Access to oligomers with diverse structural architectures [J].
Baruah, Pranjal K. ;
Gonnade, Rajesh ;
Rajamohanan, P. R. ;
Hofmann, Hans-Joerg ;
Sanjayan, Gangadhar J. .
JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (14) :5077-5084
[9]   Sophistication of foldamer form and function in vitro and in vivo [J].
Bautista, Arjel D. ;
Craig, Cody J. ;
Harker, Elizabeth A. ;
Schepartz, Alanna .
CURRENT OPINION IN CHEMICAL BIOLOGY, 2007, 11 (06) :685-692
[10]   Synthesis and helix formation of poly(m-phenylene)s bearing optically active oligo(ethylene oxide) side chains in protic media [J].
Ben, Teng ;
Goto, Hidetoshi ;
Miwa, Kazuhiro ;
Goto, Hiroaki ;
Morino, Kazuhide ;
Furusho, Yoshio ;
Yashima, Eiji .
MACROMOLECULES, 2008, 41 (12) :4506-4509