Evolution of helical foldamers

被引:118
作者
Sanford, AR [1 ]
Gong, B [1 ]
机构
[1] SUNY Buffalo, Dept Chem, Buffalo, NY 14260 USA
关键词
DE-NOVO DESIGN; NMR-SOLUTION STRUCTURE; AROMATIC SIDE-CHAINS; BETA-PEPTIDES; SECONDARY STRUCTURE; SELF-ORGANIZATION; PEPTOID OLIGOMERS; AQUEOUS-SOLUTION; LIGAND STRANDS; GAMMA-PEPTIDES;
D O I
10.2174/1385272033486260
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The overwhelming majority of unnatural foldamers described so far adopt various helical conformations. Helical foldamers include peptidomimetic oligomers such alpha-, beta- and gamma-peptides, and non-biological helices such as helicates, oligoheterocycles and olio(phenylene ethynylenes). Lying between peptidoinitnetic and non-biological foldamers are oligoarylamides whose backbones are rigidified by strong intramolecular hydrogen bonds. The localized nature of the intramolecular hydrogen bonds allows Structure the tuning of both the side chains and the curvature of the backbones, leading to helices of different surface properties and tunable interior cavities. As a result, hollow helices with interior channels Of tunable, finite diameters are generated. Thus, unnatural helical foldamers have evolved front providing examples of stably folded secondary structures to demonstrating features of higher structural levels of biomacromolecules, e.g., the creation of nanocavities.
引用
收藏
页码:1649 / 1659
页数:11
相关论文
共 101 条
[31]   Foldamers: A manifesto [J].
Gellman, SH .
ACCOUNTS OF CHEMICAL RESEARCH, 1998, 31 (04) :173-180
[32]   Helical twist sense bias in oligo(phenylene ethynylene)s induced by an optically active flexible tether [J].
Gin, MS ;
Moore, JS .
ORGANIC LETTERS, 2000, 2 (02) :135-138
[33]   Helical bias in solvophobically folded oligo(phenylene ethynylene)s [J].
Gin, MS ;
Yokozawa, T ;
Prince, RB ;
Moore, JS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (11) :2643-2644
[34]  
Gong B, 2001, CHEM-EUR J, V7, P4336, DOI 10.1002/1521-3765(20011015)7:20<4336::AID-CHEM4336>3.0.CO
[35]  
2-1
[36]   Creating nanocavities of tunable sizes: Hollow helices [J].
Gong, B ;
Zeng, HQ ;
Zhu, J ;
Yuan, LH ;
Han, YH ;
Cheng, SZ ;
Furukawa, M ;
Parra, RD ;
Kovalevsky, AY ;
Mills, JL ;
Skrzypczak-Jankun, E ;
Martinovic, S ;
Smith, RD ;
Zheng, C ;
Szyperski, T ;
Zeng, XC .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2002, 99 (18) :11583-11588
[37]   Solid phase synthesis of β-peptoids:: N-substituted β-aminopropionic acid oligomers [J].
Hamper, BC ;
Kolodziej, SA ;
Scates, AM ;
Smith, RG ;
Cortez, E .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (03) :708-718
[38]   Novel folding patterns in a family of oligoanthranilamides: Non-peptide oligomers that form extended helical secondary structures [J].
Hamuro, Y ;
Geib, SJ ;
Hamilton, AD .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (44) :10587-10593
[39]   MOLECULAR HELICITY - A GENERAL-APPROACH FOR HELICITY INDUCTION IN A POLYHETEROCYCLIC MOLECULAR STRAND [J].
HANAN, GS ;
LEHN, JM ;
KYRITSAKAS, N ;
FISCHER, J .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1995, (07) :765-766
[40]   Design of secondary structures in unnatural peptides:: Stable helical γ-tetra-, hexa-, and octapeptides and consequences of α-substitution [J].
Hanessian, S ;
Luo, XH ;
Schaum, R ;
Michnick, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (33) :8569-8570