Self-assembling urea-based peptidomimetics: A simple one-step synthesis and crystal structure of core beta-alanyl ureylene retro-bispeptides (MeO-A(aa)-[NH-CO-NH]-CH2-CH2-CO-NH-A(aa)-OMe; A(aa)=amino acid A)

被引:19
作者
Ranganathan, D
Kurur, S
Madhusudanan, KP
Karle, IL
机构
[1] CENT DRUG RES INST,LUCKNOW 226001,UTTAR PRADESH,INDIA
[2] USN,RES LAB,STRUCT MATTER LAB,WASHINGTON,DC 20375
关键词
D O I
10.1016/S0040-4039(97)00960-X
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A novel family of urea-based peptidomimetics containing beta-alanyl unit at the core has been synthesized by a simple one-step procedure. Solid state structures of some representative examples have showm self-assembly into highly ordered extended hydrogen-bonded chains and ribbons with modest NLO activity. (C) 1997 Elsevier Science Ltd.
引用
收藏
页码:4659 / 4662
页数:4
相关论文
共 21 条
[2]  
BERGMAN J, 1976, TETRAHEDRON LETT, P3615
[3]   SOLID-PHASE SYNTHESES OF UNNATURAL BIOPOLYMERS CONTAINING REPEATING UREA UNITS [J].
BURGESS, K ;
LINTHICUM, DS ;
SHIN, HW .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1995, 34 (08) :907-909
[4]   Solid phase syntheses of oligoureas [J].
Burgess, K ;
Ibarzo, J ;
Linthicum, DS ;
Russell, DH ;
Shin, H ;
Shitangkoon, A ;
Totani, R ;
Zhang, AJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (07) :1556-1564
[5]  
CHANG YL, 1993, J AM CHEM SOC, V115, P599
[6]   A DOZEN YEARS OF RETRO-INVERSO PEPTIDOMIMETICS [J].
CHOREV, M ;
GOODMAN, M .
ACCOUNTS OF CHEMICAL RESEARCH, 1993, 26 (05) :266-273
[7]  
GANTE J, 1994, ANGEW CHEM INT EDIT, V33, P1699, DOI 10.1002/anie.199416991
[8]   PEPTIDOMIMETICS FOR RECEPTOR LIGANDS DISCOVERY, DEVELOPMENT, AND MEDICAL PERSPECTIVES [J].
GIANNIS, A .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1993, 32 (09) :1244-1267
[9]   MEDICINAL CHEMISTRY IN THE GOLDEN-AGE OF BIOLOGY - LESSONS FROM STEROID AND PEPTIDE RESEARCH [J].
HIRSCHMANN, R .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1991, 30 (10) :1278-1301
[10]   REACTION OF HYDROXAMIC ACIDS WITH WATER-SOLUBLE CARBODIIMIDES . A LOSSEN REARRANGEMENT [J].
HOARE, DG ;
OLSON, A ;
KOSHLAND, DE .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1968, 90 (06) :1638-&