Inhibitors of the bacterial cell wall biosynthesis enzyme MurC

被引：54

作者：

Reck, F

Marmor, S

Fisher, S

Wuonola, MA

机构：

[1] AstraZeneca R&D Boston, Infect Discovery, Chem, Waltham, MA 02451 USA

[2] AstraZeneca R&D Boston, Infect Discovery, Biochem, Waltham, MA 02451 USA

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2001年 / 11卷 / 11期

关键词：

D O I：

10.1016/S0960-894X(01)00251-7

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

A series of phosphinate transition-state analogues of the L-alanine adding enzyme (MurC) of bacterial peptidoglycan biosynthesis was prepared and tested as inhibitors of the Escherichia coli enzyme. Compound 4 was identified as a potent inhibitor of MurC from Escherichia coli with an IC50 Of 49 nM. (C) 2001 Elsevier Science Ltd. All rights reserved.

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页码：1451 / 1454

页数：4

相关论文

共 13 条

[1] 1,1-Diethoxyethylphosphinates and phosphonites. Intermediates for the synthesis of functional phosphorus acids [J].

Baylis, EK .

TETRAHEDRON LETTERS, 1995, 36 (51) :9385-9388

[2]

BOCQUEL MT, 1997, GENETICS MOL BIOL H, V2, P285

[3] Formation of adenosine 5′-tetraphosphate from the acyl phosphate intermediate:: a difference between the MurC and MurD synthetases of Escherichia coli [J].

Bouhss, A ;

Dementin, S ;

van Heijenoort, J ;

Parquet, C ;

Blanot, D .

FEBS LETTERS, 1999, 453 (1-2) :15-19

[4] Biochemical evidence for the formation of a covalent acyl-phosphate linkage between UDP-N-acetylmuramate and ATP in the Escherichia coli UDP-N-acetylmuramate:L-alanine lipase-catalyzed reaction [J].

Falk, PJ ;

Ervin, KM ;

Volk, KS ;

Ho, HT .

BIOCHEMISTRY, 1996, 35 (05) :1417-1422

[5] PHOSPHINIC ACID ANALOGS OF GABA .1. NEW POTENT AND SELECTIVE GABA(B) AGONISTS [J].

FROESTL, W ;

MICKEL, SJ ;

HALL, RG ;

VONSPRECHER, G ;

STRUB, D ;

BAUMANN, PA ;

BRUGGER, F ;

GENTSCH, C ;

JAEKEL, J ;

OLPE, HR ;

RIHS, G ;

VASSOUT, A ;

WALDMEIER, PC ;

BITTIGER, H .

JOURNAL OF MEDICINAL CHEMISTRY, 1995, 38 (17) :3297-3312

[6] Inhibitors of the bacterial cell wall biosynthesis enzyme MurD [J].

Gegnas, LD ;

Waddell, ST ;

Chabin, RM ;

Reddy, S ;

Wong, KK .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1998, 8 (13) :1643-1648

[7] A CONVENIENT PREPARATIVE METHOD OF CARBOHYDRATE PHOSPHATES WITH BUTYLLITHIUM AND PHOSPHOROCHLORIDATE [J].

INAGE, M ;

CHAKI, H ;

KUSUMOTO, S ;

SHIBA, T .

CHEMISTRY LETTERS, 1982, (08) :1281-1284

[8] IMPROVED ASSAY FOR NANOMOLE AMOUNTS OF INORGANIC-PHOSPHATE [J].

LANZETTA, PA ;

ALVAREZ, LJ ;

REINACH, PS ;

CANDIA, OA .

ANALYTICAL BIOCHEMISTRY, 1979, 100 (01) :95-97

[9] PHOSPHINIC ACID INHIBITORS OF D-ALANYL-D-ALANINE LIGASE [J].

PARSONS, WH ;

PATCHETT, AA ;

BULL, HG ;

SCHOEN, WR ;

TAUB, D ;

DAVIDSON, J ;

COMBS, PL ;

SPRINGER, JP ;

GADEBUSCH, H ;

WEISSBERGER, B ;

VALIANT, ME ;

MELLIN, TN ;

BUSCH, RD .

JOURNAL OF MEDICINAL CHEMISTRY, 1988, 31 (09) :1772-1778

[10] Phosphinate inhibitors of the D-glutamic acid-adding enzyme of peptidoglycan biosynthesis [J].

Tanner, ME ;

Vaganay, S ;

vanHeijenoort, J ;

Blanot, D .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (05) :1756-1760