Synthesis of deoxygenated α(1 → 5)-linked arabinofuranose disaccharides as substrates and inhibitors of arabinosyltransferases of Mycobacterium tuberculosis

被引：16

作者：

Pathak, Ashish K. ^{[1
]}

Pathak, Vibha ^{[1
]}

Suling, William J. ^{[1
]}

Riordan, James R. ^{[1
]}

Gurcha, Sudagar S. ^{[2
]}

Besra, Gurdyal S. ^{[2
]}

Reynolds, Robert C. ^{[1
]}

机构：

[1] So Res Inst, Drug Discovery Div, Birmingham, AL 35255 USA

[2] Univ Birmingham, Sch Biosci, Birmingham B15 2TT, W Midlands, England

来源：

BIOORGANIC & MEDICINAL CHEMISTRY | 2009年 / 17卷 / 02期

基金：

英国医学研究理事会;

关键词：

Arabinosyltransferases; Mycobacterium tuberculosis; Deoxyarabinofuranose; 2-Fluoroarabinofuranose; Disaccharides; Inhibitors; DRUG-RESISTANT TUBERCULOSIS; HIV-INFECTED PATIENTS; STEREOSELECTIVE-SYNTHESIS; MULTIDRUG-RESISTANT; TRANSFERASE-ACTIVITY; DERIVATIVES; ANALOGS; GLYCOSYLATION; BIOSYNTHESIS; EPIDEMIOLOGY;

D O I：

10.1016/j.bmc.2008.11.027

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Arabinosyltransferases (AraTs) play a critical role in mycobacterial cell wall biosynthesis and are potential drug targets for the treatment of tuberculosis, especially multi-drug resistant forms of M. tuberculosis (MTB). Herein, we report the synthesis and acceptor/inhibitory activity of Araf alpha(1 -> 5) Araf disaccharides possessing deoxygenation at the reducing sugar of the disaccharide. Deoxygenation at either the C-2 or C-3 position of Araf was achieved via a free radical procedure using xanthate derivatives of the hydroxyl group. The alpha(1 -> 5)-linked disaccharides were produced by coupling n-octyl alpha-Araf 2-/3-deoxy, 2-fluoro glycosyl acceptors with an Araf thioglycosyl donor. The target disaccharides were tested in a cell free mycobacterial AraTs assay as well as an in vitro assay against MTB H37Ra and M. avium complex strains. (C) 2008 Elsevier Ltd. All rights reserved.

引用

页码：872 / 881

页数：10

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