Novel consecutive β- and γ-turn mimetics composed of α-aminooxy tripeptides

被引:18
作者
Baek, BH [1 ]
Lee, MR [1 ]
Kim, KY [1 ]
Cho, UI [1 ]
Boo, DW [1 ]
Shin, I [1 ]
机构
[1] Yonsei Univ, Dept Chem, Seoul 120749, South Korea
关键词
D O I
10.1021/ol020233q
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHIC] To develop novel consecutive beta- and gamma-turn mimetics, we designed and characterized alpha-aminooxy tripeptides (trimers) consisting of oxanipecotic acid dimer and alpha-aminooxy acid. According to FT-IR and NMR data, as well as ab initio quantum calculations, the trimers adopted unusual folded structures with consecutive beta- and gamma-turnlike conformations.
引用
收藏
页码:971 / 974
页数:4
相关论文
共 19 条
[1]  
Brickmann K, 1999, CHEM-EUR J, V5, P2241
[2]   β-peptides:: From structure to function [J].
Cheng, RP ;
Gellman, SH ;
DeGrado, WF .
CHEMICAL REVIEWS, 2001, 101 (10) :3219-3232
[3]   Stereochemical control of hairpin formation in β-peptides containing dinipecotic acid reverse turn segments [J].
Chung, YJ ;
Huck, BR ;
Christianson, LA ;
Stanger, HE ;
Krauthäuser, S ;
Powell, DR ;
Gellman, SH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (17) :3995-4004
[4]  
Creighton TE, 1993, PROTEINS STRUCTURES
[5]  
Frisch M.J., 2016, Gaussian 16 Revision C. 01. 2016, V16, P01
[6]   A field guide to foldamers [J].
Hill, DJ ;
Mio, MJ ;
Prince, RB ;
Hughes, TS ;
Moore, JS .
CHEMICAL REVIEWS, 2001, 101 (12) :3893-4011
[7]   Promotion of sheet formation in α-peptide strands by a β-peptide reverse turn [J].
Huck, BR ;
Fisk, JD ;
Gellman, SH .
ORGANIC LETTERS, 2000, 2 (17) :2607-2610
[8]   A γ-turn induced by a highly constrained cyclopropane analogue of phenylalanine (c3diPhe) in the solid state [J].
Jiménez, AI ;
Cativiela, C ;
Marraud, M .
TETRAHEDRON LETTERS, 2000, 41 (28) :5353-5356
[9]   H-1-NMR STUDIES OF RECEPTOR-SELECTIVE SUBSTANCE-P ANALOGS REVEAL DISTINCT PREDOMINANT CONFORMATIONS IN DMSO-D6 [J].
LEVIANTEITELBAUM, D ;
KOLODNY, N ;
CHOREV, M ;
SELINGER, Z ;
GILON, C .
BIOPOLYMERS, 1989, 28 (01) :51-64
[10]   TRANSFERRED NUCLEAR OVERHAUSER EFFECT ANALYSES OF MEMBRANE-BOUND ENKEPHALIN ANALOGS BY H-1 NUCLEAR MAGNETIC-RESONANCE - CORRELATION BETWEEN ACTIVITIES AND MEMBRANE-BOUND CONFORMATIONS [J].
MILON, A ;
MIYAZAWA, T ;
HIGASHIJIMA, T .
BIOCHEMISTRY, 1990, 29 (01) :65-75