Strained-cyclophane-induced β-turn template:: Design, synthesis, and spectroscopic characterization

被引:25
作者
Cristau, P [1 ]
Martin, MT
Dau, METH
Vors, JP
Zhu, JP
机构
[1] CNRS, Inst Chim Subst Nat, F-91198 Gif Sur Yvette, France
[2] Bayer CropSci, F-69009 Lyon, France
关键词
D O I
10.1021/ol0488439
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Three tetrapeptides incorporating a 14-membered (Ri+1, Si+2) cycloisodityrosine at the i + 1 and i + 2 positions were designed and synthesized. Conformational analysis by H-1 NMR and CD spectra as well as molecular modeling indicated that they all adopt a beta-turn conformation. While the CD spectrum of compound 2 is characteristic of the typical type-II beta-turn (maximum at similar to200 nm and a minimum at similar to220 nm), that of 1a (atropisomer of 2) is opposite in sign to the expected spectrum of the type-II beta-turn.
引用
收藏
页码:3183 / 3186
页数:4
相关论文
共 27 条
[1]   BETA-TURN TOPOGRAPHY [J].
BALL, JB ;
HUGHES, RA ;
ALEWOOD, PF ;
ANDREWS, PR .
TETRAHEDRON, 1993, 49 (17) :3467-3478
[2]   Synthesis of cycloisodityrosine revisited: A selective ring forming process [J].
Bigot, A ;
Zhu, JP .
TETRAHEDRON LETTERS, 1998, 39 (07) :551-554
[3]   Synthesis and conformational studies of β-turn mimetic incorporated in leu-enkephalin [J].
Blomberg, D ;
Hedenström, M ;
Kreye, P ;
Sethson, I ;
Brickmann, K ;
Kihlberg, J .
JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (10) :3500-3508
[4]   Synthesis of (9R,12S)- and (9S,12S)-cycloisodityrosine and their N-methyl derivatives [J].
Boger, DL ;
Zhou, JC ;
Borzilleri, RM ;
Nukui, S ;
Castle, SL .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (07) :2054-2069
[5]   Total synthesis of an atropdiastereomer of RP-66453 and determination of its absolute configuration [J].
Bois-Choussy, M ;
Cristau, P ;
Zhu, JP .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (35) :4238-4241
[6]   Solid-phase syntheses of β-turn analogues to mimic or disrupt protein-protein interactions [J].
Burgess, K .
ACCOUNTS OF CHEMICAL RESEARCH, 2001, 34 (10) :826-835
[7]  
Eliel E. L., 1994, STEREOCHEMISTRY ORGA
[8]   Stereochemical implications on diversity in β-turn peptidomimetic libraries [J].
Feng, YB ;
Pattarawarapan, M ;
Wang, ZC ;
Burgess, K .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (25) :9175-9177
[9]   Design, synthesis, and conformational analysis of a proposed type I β-turn mimic [J].
Fink, BE ;
Kym, PR ;
Katzenellenbogen, JA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (18) :4334-4344
[10]   Effect of sequence on peptide geometry in 5-tert-butylprolyl type VI β-turn mimics [J].
Halab, L ;
Lubell, WD .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (11) :2474-2484