Small ring constrained peptidomimetics.: Synthesis of aziridine parallel β-sheet mimetics

被引:29
作者
Filigheddu, SN [1 ]
Taddei, M [1 ]
机构
[1] Univ Sassari, Dipartimento Chim, I-07100 Sassari, Italy
关键词
D O I
10.1016/S0040-4039(98)00632-7
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The synthesis of a series of novel amino acids and peptides containing an aziridine ring is described. Their preparation is based on the Gabriel-Cromwell reaction of amino acids or peptides with different 2-bromo acrylates and acrylamides. These products are constituted by a turned scaffold (the aziridine) where two parallel peptidic strands can be grown to produce a beta-sheet mimetic. (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:3857 / 3860
页数:4
相关论文
共 14 条
[1]   Synthesis of enantiomerically pure trans aziridine-2-carboxylates by diastereoselective Gabriel-Cromwell reaction [J].
Cardillo, G ;
Gentilucci, L ;
Tomasini, C ;
CastejonBordas, MPV .
TETRAHEDRON-ASYMMETRY, 1996, 7 (03) :755-762
[2]   CrCl2 mediated addition of allylic halides or phosphates to N-protected alpha-amino aldehydes. Stereocontrolled synthesis of a new core for C-2 symmetric HIV-protease inhibitors. [J].
Ciapetti, P ;
Falorni, M ;
Taddei, M .
TETRAHEDRON, 1996, 52 (21) :7379-7390
[3]  
GANTE J, 1994, ANGEW CHEM INT EDIT, V33, P1699, DOI 10.1002/anie.199416991
[4]   AUXILIARY MEDIATED SYNTHESIS OF AZIRIDINE-2-CARBOXYLIC ACID-DERIVATIVES [J].
GARNER, P ;
DOGAN, O ;
PILLAI, S .
TETRAHEDRON LETTERS, 1994, 35 (11) :1653-1656
[5]  
KAHN M, 1993, SYNLETT, P821
[6]   A general synthesis of oligopeptides containing an oxirane ring in the place of a peptidic bond [J].
Mann, A ;
Quaranta, L ;
Reginato, G ;
Taddei, M .
TETRAHEDRON LETTERS, 1996, 37 (15) :2651-2654
[7]  
Marvel C. S., 1939, J AM CHEM SOC, V61, P3156
[8]  
NAGEL DL, 1971, J ORG CHEM, V36, P3911
[9]   Artificial beta-sheets [J].
Nowick, JS ;
Smith, EM ;
Pairish, M .
CHEMICAL SOCIETY REVIEWS, 1996, 25 (06) :401-&
[10]   Molecular scaffolds .4. An artificial beta-sheet comprising a molecular scaffold, a beta-strand mimic, and a peptide strand [J].
Nowick, JS ;
Holmes, DL ;
Mackin, G ;
Noronha, G ;
Shaka, AJ ;
Smith, EM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (11) :2764-2765