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
[11]   CONFORMATIONAL-ANALYSIS OF CYCLOLINOPEPTIDE A, A CYCLIC NONAPEPTIDE - NUCLEAR OVERHAUSER EFFECT AND ENERGY MINIMIZATION STUDIES [J].
RAGHOTHAMA, S ;
RAMAKRISHNAN, C ;
BALASUBRAMANIAN, D ;
BALARAM, P .
BIOPOLYMERS, 1989, 28 (02) :573-588
[12]   TURNS IN PEPTIDES AND PROTEINS [J].
ROSE, GD ;
GIERASCH, LM ;
SMITH, JA .
ADVANCES IN PROTEIN CHEMISTRY, 1985, 37 :1-109
[13]   Design, synthesis, and biological activities of four angiotensin II receptor ligands with gamma-turn mimetics replacing amino acid residues 3-5 [J].
Schmidt, B ;
Lindman, S ;
Tong, WM ;
Lindeberg, G ;
Gogoll, A ;
Lai, ZN ;
Thornwall, M ;
Synnergren, B ;
Nilsson, A ;
Welch, CJ ;
Sohtell, M ;
Westerlund, C ;
Nyberg, F ;
Karlen, A ;
Hallberg, A .
JOURNAL OF MEDICINAL CHEMISTRY, 1997, 40 (06) :903-919
[14]   Synthesis of optically active phthaloyl D-aminooxy acids from L-amino acids or L-hydroxy acids as building blocks for the preparation of aminooxy peptides [J].
Shin, I ;
Lee, MR ;
Lee, J ;
Jung, M ;
Lee, W ;
Yoon, J .
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (22) :7667-7675
[15]   REVERSE TURNS IN PEPTIDES AND PROTEINS [J].
SMITH, JA ;
PEASE, LG .
CRC CRITICAL REVIEWS IN BIOCHEMISTRY, 1980, 8 (04) :315-399
[16]   β-turn mimetic library synthesis:: scaffolds and applications [J].
Souers, AJ ;
Ellman, JA .
TETRAHEDRON, 2001, 57 (35) :7431-7448
[17]  
Tooze J., 1999, INTRO PROTEIN STRUCT
[18]   Conformation of desmopressin, an analogue of the peptide hormone vasopressin, in aqueous solution as determined by NMR spectroscopy [J].
Walse, B ;
Kihlberg, J ;
Drakenberg, T .
EUROPEAN JOURNAL OF BIOCHEMISTRY, 1998, 252 (03) :428-440
[19]   Synthesis and characterization of chiral N-O turns induced by α-aminoxy acids [J].
Yang, D ;
Li, B ;
Ng, FF ;
Yan, YL ;
Qu, J ;
Wu, YD .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (22) :7303-7312