Solid supported high-throughput organic synthesis of peptide β-turn mimetics via Petasis reaction/diketopiperazine formation

被引：54

作者：

Golebiowski, A ^{[1
]}

Klopfenstein, SR ^{[1
]}

Chen, JJ ^{[1
]}

Shao, X ^{[1
]}

机构：

[1] Proctor & Gamble Pharmaceut, Combinatorial Chem Grp, Hlth Care Res Ctr, Mason, OH 45040 USA

来源：

TETRAHEDRON LETTERS | 2000年 / 41卷 / 25期

关键词：

solid-phase synthesis; Petasis reaction; peptide beta-turn mimetics; combinatorial chemistry; bicyclic heterocyclic compounds;

D O I：

10.1016/S0040-4039(00)00669-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

High-throughput organic synthesis of bicyclic diketopiperazines 1, beta-turn mimetics, is described. Starting from Merrifield resin-bound piperazine-2-carboxylic acid, first two (R-4 and R-5) Side chains are introduced via the Petasis reaction and subsequent amide bond formation. Unblocking the a-amino group of piperazine-2-carboxylic acid, Boc-N-protected alpha-amino acid coupling and deprotection followed by cyclative cleavage introduces the remaining R-2 and R-1 side chains. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：4841 / 4844

页数：4

共 12 条

[1] PEPTIDOMIMETICS FOR RECEPTOR LIGANDS DISCOVERY, DEVELOPMENT, AND MEDICAL PERSPECTIVES
GIANNIS, A
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1993, 32 (09) : 1244 - 1267
[2] Gillespie P, 1997, BIOPOLYMERS, V43, P191, DOI 10.1002/(SICI)1097-0282(1997)43:3<191::AID-BIP2>3.3.CO
[3] 2-2
[4] Rationally designed non-peptides: Variously substituted piperazine libraries for the discovery of bradykinin antagonists and other G-protein-coupled receptor ligands
Goodfellow, VS
Laudeman, CP
Gerrity, JI
Burkard, M
Strobel, E
Zuzack, JS
McLeod, DA
[J]. MOLECULAR DIVERSITY, 1996, 2 (1-2) : 97 - 102
[5] Design and synthesis of conformationally constrained amino acids as versatile scaffolds and peptide mimetics
Hanessian, S
McNaughtonSmith, G
Lombart, HG
Lubell, WD
[J]. TETRAHEDRON, 1997, 53 (38) : 12789 - 12854
[6] KAHN M, 1993, SYNLETT, P821
[7] A practical synthesis of peptide mimetics via the solid-phase Petasis reaction
Klopfenstein, SR
Chen, JJ
Golebiowski, A
Li, M
Peng, SX
Shao, X
[J]. TETRAHEDRON LETTERS, 2000, 41 (25) : 4835 - 4839
[8] MAARSEVEEN JH, 1998, COMB CHEM HIGH T SCR, V1, P185
[9] THE BORONIC ACID MANNICH REACTION - A NEW METHOD FOR THE SYNTHESIS OF GEOMETRICALLY PURE ALLYLAMINES
PETASIS, NA
AKRITOPOULOU, I
[J]. TETRAHEDRON LETTERS, 1993, 34 (04) : 583 - 586
[10] TURNS IN PEPTIDES AND PROTEINS
ROSE, GD
GIERASCH, LM
SMITH, JA
[J]. ADVANCES IN PROTEIN CHEMISTRY, 1985, 37 : 1 - 109

← 1 2 →