The synthesis of diaminopimelic acid containing peptidoglycan fragments using metathesis cross coupling

被引:44
作者
Chowdhury, AR [1 ]
Boons, GJ [1 ]
机构
[1] Univ Georgia, Complex Carbohydrate Res Ctr, Athens, GA 30602 USA
基金
美国国家卫生研究院;
关键词
peptidoglycan; amino acid; cross metathesis; meso-2,6-diaminopimelic acid;
D O I
10.1016/j.tetlet.2005.01.062
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Properly protected diaminopimelic acid (DAP), a component of peptidoglycan of Gram-negative bacteria, was prepared by a metathesis cross coupling between properly protected allyl and vinyl glycine derivatives using Grubb's second-generation catalyst followed by reduction of the double bond of the resulting Compound. The DAP derivatives were used in the solution and polymer-supported synthesis of biological active peptides. (C) 2005 Published by Elsevier Ltd.
引用
收藏
页码:1675 / 1678
页数:4
相关论文
共 29 条
[1]   Toll-like receptor signalling [J].
Akira, S ;
Takeda, K .
NATURE REVIEWS IMMUNOLOGY, 2004, 4 (07) :499-511
[2]   Innate immunity via Toll-like receptors and Nod proteins [J].
Athman, R ;
Philpott, D .
CURRENT OPINION IN MICROBIOLOGY, 2004, 7 (01) :25-32
[3]   Cross-metathesis of unsaturated α-amino acid derivatives [J].
Biagini, SCG ;
Gibson, SE ;
Keen, SP .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1998, (16) :2485-2499
[4]   Nods, Nalps and Naip: intracellular regulators of bacterial-induced inflammation [J].
Chamaillard, M ;
Girardin, SE ;
Viala, J ;
Philpott, DJ .
CELLULAR MICROBIOLOGY, 2003, 5 (09) :581-592
[5]   A general model for selectivity in olefin cross metathesis [J].
Chatterjee, AK ;
Choi, TL ;
Sanders, DP ;
Grubbs, RH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (37) :11360-11370
[6]   A concise, stereoselective synthesis of meso-2,6-diaminopimelic acid (DAP) [J].
Collier, PN ;
Patel, I ;
Taylor, RJK .
TETRAHEDRON LETTERS, 2001, 42 (34) :5953-5954
[7]   Bacterial diaminopimelate metabolism as a target for antibiotic design [J].
Cox, RJ ;
Sutherland, A ;
Vederas, JC .
BIOORGANIC & MEDICINAL CHEMISTRY, 2000, 8 (05) :843-871
[8]   Asymmetric synthesis of (2S,6S)- and meso-(2S,6R)-diaminopimelic acids from enantiopure bis(sulfinimines) [J].
Davis, FA ;
Srirajan, V .
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (10) :3248-3251
[10]   Stereoselective synthesis of meso-2,6-diaminopimelic acid and its selectively protected derivatives [J].
Gao, Y ;
Lane-Bell, P ;
Vederas, JC .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (07) :2133-2143