An improved total synthesis of UDP-N-acetyl-muramic acid

被引：12

作者：

Babic, Andrej

Pecar, Slavko

机构：

[1] Univ Ljubljana, Fac Pharm, Ljubljana 1000, Slovenia

[2] Jozef Stefan Inst, Ljubljana 1000, Slovenia

来源：

TETRAHEDRON LETTERS | 2007年 / 48卷 / 25期

关键词：

UDP-Mur-N-Ac; total synthesis; MurC; diphosphates;

D O I：

10.1016/j.tetlet.2007.04.098

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Biochemical testing for novel inhibitors of Mur ligases requires several commercially unavailable and structurally complex substrates. We describe a modified synthetic strategy for the total chemical synthesis of the MurC ligase substrate UDP-Nacetyl-muramic acid which includes several improvements over published methods, especially with regard to purification procedures. The synthetic strategy is applicable for the synthesis of further Mur ligase substrates. (c) 2007 Elsevier Ltd. All rights reserved.

引用

收藏

页码：4403 / 4405

页数：3

相关论文

共 20 条

[1] Pulvinones as bacterial cell wall biosynthesis inhibitors [J].

Antane, S ;

Caufield, CE ;

Hu, W ;

Keeney, D ;

Labthavikul, P ;

Morris, K ;

Naughton, SM ;

Petersen, PJ ;

Rasmussen, BA ;

Singh, G ;

Yang, YJ .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2006, 16 (01) :176-180

[2] OVEREXPRESSION, PURIFICATION, AND MECHANISTIC STUDY OF UDP-N-ACETYLENOLPYRUVYLGLUCOSAMINE REDUCTASE [J].

BENSON, TE ;

MARQUARDT, JL ;

MARQUARDT, AC ;

ETZKORN, FA ;

WALSH, CT .

BIOCHEMISTRY, 1993, 32 (08) :2024-2030

[3]

BLANOT D, 1994, CARBOHYD RES, V252, P107

[4] Synthesis of 5-deoxy-5-phospho-D-ribonohydroxamic acid:: a new competitive and selective inhibitor of type B ribose-5-phosphate isomerase from Mycobacterium tuberculosis [J].

Burgos, E ;

Roos, AK ;

Mowbray, SL ;

Salmon, L .

TETRAHEDRON LETTERS, 2005, 46 (21) :3691-3694

[5] Development of an LC-MS based enzyme activity assay for MurC: application to evaluation of inhibitors and kinetic analysis [J].

Deng, GJ ;

Gu, RF ;

Marmor, S ;

Fisher, SL ;

Jahic, H ;

Sanyal, G .

JOURNAL OF PHARMACEUTICAL AND BIOMEDICAL ANALYSIS, 2004, 35 (04) :817-828

[6] Multi gram synthesis of UDP-N-acetylmuramic acid [J].

Dini, C ;

Drochon, N ;

Ferrari, P ;

Aszodi, J .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2000, 10 (02) :143-145

[7] Structure and function of the Mur enzymes: development of novel inhibitors [J].

El Zoeiby, A ;

Sanschagrin, F ;

Levesque, RC .

MOLECULAR MICROBIOLOGY, 2003, 47 (01) :1-12

[8]

GROSS PH, 1986, LIEBIGS ANN CHEM, P37

[9] A new approach towards peptidosulfonamides: synthesis of potential inhibitors of bacterial peptidoglycan biosynthesis enzymes MurD and MurE [J].

Humljan, Jan ;

Kotnik, Miha ;

Boniface, Audrey ;

Solmajer, Tomaz ;

Urleb, Uros ;

Blanot, Didier ;

Gobec, Stanislav .

TETRAHEDRON, 2006, 62 (47) :10980-10988

[10] Synthesis of unnatural sugar nucleotides and their evaluation as donor substrates in glycosyltransferase-catalyzed reactions [J].

Khaled, A ;

Ivannikova, T ;

Augé, C .

CARBOHYDRATE RESEARCH, 2004, 339 (16) :2641-2649