Ligand view of UDP-N-acetyl-3-O-(1-carboxyvinyl)-alpha-D-glucosamine (7301 - BEGZZYPUNCJHKP-DBYWSUQTSA-N)

C₂₀H₂₉N₃O₁₉P₂

UDP-N-acetyl-3-O-(1-carboxyvinyl)-alpha-D-glucosamine

BEGZZYPUNCJHKP-DBYWSUQTSA-N

BRENDA

KEGG

Amino sugar and nucleotide sugar metabolism, Biosynthesis of nucleotide sugars, Peptidoglycan biosynthesis

MetaCyc

anhydromuropeptides recycling I, UDP-N-acetylmuramoyl-pentapeptide biosynthesis I (meso-diaminopimelate containing), UDP-N-acetylmuramoyl-pentapeptide biosynthesis II (lysine-containing), UDP-N-acetylmuramoyl-pentapeptide biosynthesis III (meso-diaminopimelate containing)

ATP + UDP-N-acetylglucosaminyl-enoylpyruvate + L-Ala = ADP + phosphate + UDP-N-acetylglucosaminyl-enoylpyruvoyl-L-Ala

substrate inhibition at pH 6, Ki 0.01 mM with 0.15 mM NADPH, weaker at more basic pH

-

Over-production, purification and properties of the uridine-diphosphate-N-acetylmuramate:L-alanine ligase from Escherichia coli

1995

Liger, S.; Masson, A.; Blanot, D.; van Heijenoort, J.; Parquet, C.

Eur. J. Biochem.

230

80-87

286059

36973

Purification of UDP-N-acetylenolpyruvoylglucosamine reductase from Escherichia coli by affinity chromatography, its subunit structure and the absence of flavin as the prosthetic group

1979

Anwar, R.A.; Vlaovic, M.

Can. J. Biochem.

57

188-196

286060

4143897

Partial purification and some properties of the uridine diphospho-N-acetylglucosamine-enolpyruvate reductase from Staphylococcus epidermidis

1973

Wickus, G.G.; Rubenstein, P.A.; Warth, A.D.; Strominger, J.L.

J. Bacteriol.

113

291-294

286062

6222035

Pool levels of UDP N-acetylglucosamine and UDP N-acetylglucosamine-enolpyruvate in Escherichia coli and correlation with peptidoglycan synthesis

1983

Mengin-Lecreulx, D.; Flouret, B.; van Heijenoort, J.

J. Bacteriol.

154

1284-1290

286063

4394163

Biosynthesis of uridine diphospho-N-acetylmuramic acid. 3. Purification and properties of uridine diphospho-N-acetylenolpyruvyl-glucosamine reductase

1970

Taku, A.; Gunetileke, K.G.; Anwar, R.A.

J. Biol. Chem.

245

5012-5016

286064

4717533

Biosynthesis of uridine diphospho-N-acetylmuramic acid. IV. Activation of uridine diphospho-N-acetylenolpyruvylglucosamine reductase by monovalent cations

1973

Taku, A.; Anwar, R.A.

J. Biol. Chem.

248

4971-4976

286065

7727397

Steady-state kinetic mechanism of Escherichia coli UDP-N-acetylenolpyruvylglucosamine reductase

1995

Dhalla, A.M.; Yanchunas, J.Jr.; Ho, H.T.; Falk, P.J.; Villafranca, J.J.; Robertson, J.G.

Biochemistry

34

5390-5402

286066

8448160

Overexpression, purification, and mechanistic study of UDP-N-acetylenolpyruvylglucosamine reductase

1993

Benson, T.E.; Marquardt, J.L.; Marquardt, A.C.; Etzkorn, F.A.; Walsh, C.T.

Biochemistry

32

2024-2030

286067

9020777

Kinetic characterization of wild-type and S229A mutant MurB: evidence of the role of Ser 229 as a general acid

1997

Benson, T.E.; Walsh, C.T.; Massey, V.

Biochemistry

36

796-805

286068

11284731

Identification and characterization of UDP-N-acetylenolpyruvylglucosamine reductase (MurB) from the gram-positive pathogen Streptococcus pneumoniae

2001

Sylvester, D.R.; Alvarez, E.; Patel, A.; Ratnam, K.; Kallender, H.; Wallis, N.G.

Biochem. J.

355

431-435

286071

11418774

Crystallisation and preliminary X-ray analysis of UDP-N-acetylenolpyruvylglucosamine reductase (MurB) from Staphylococcus aureus

2001

Harris, M.S.; Herberg, J.T.; Cialdella, J.I.; Martin, J.T., Jr.; Benson, T.E.; Choi, G.H.; Baldwin, E.T.

Acta Crystallogr. Sect. D

57

1032-1035

637587

5699062

Biosynthesis of uridine diphospho-N-acetylmuramic acid. II. Purification and properties of pyruvate-uridine diphospho-N-acetylglucosamine transferase and characterization of uridine diphospho-N-acetylenopyruvylglucosamine

1968

Gunetileke, K.G.; Anwar, R.A.

J. Biol. Chem.

243

5770-5778

637588

1123336

Pyruvate-uridine diphospho-N-acetylglucosamine transferase. Purification to homogeneity and feedback inhibition

1975

Zemell, R.I.; Anwar, R.A.

J. Biol. Chem.

250

3185-3192

637589

1150648

Mechanism of pyruvate-uridine diphospho-N-acetylglucosamine transferase. Evidence for an enzyme-enolpyruvate intermediate

1975

Zemell, R.I.; Anwar, R.A.

J. Biol. Chem.

250

4959-4964

637590

4197158

Inhibition of phosphoenolpyruvate:uridine diphosphate N-acetylglucosamine enolpyruvyltransferase by uridine diphosphate N-acetylmuramyl peptides

1973

Venkateswaran, P.S.; Lugtenberg, E.J.J.; Wu, H.C.

Biochim. Biophys. Acta

293

570-574

637591

4688141

Partial purification and properties of the pyruvate-uridine diphospho-N-acetylglucosamine transferase from Staphylococcus epidermidis

1973

Wickus, G.G.; Strominger, J.L.

J. Bacteriol.

113

287-290

637592

1577165

The UDP-N-acetylglucosamine 1-carboxyvinyl-transferase of Enterobacter cloacae. Molecular cloning, sequencing of the gene and overexpression of the enzyme

1992

Wanke, C.; Falchetto, R.; Amrhein, N.

FEBS Lett.

301

271-276

637593

1512209

Cloning and sequencing of Escherichia coli murZ and purification of its product, a UDP-N-acetylglucosamine enolpyruvyl transferase

1992

Marquardt, J.L.; Siegele, D.A.; Kolter, R.; Walsh, C.T.

J. Bacteriol.

174

5748-5752

637594

7213646

Effect of phosphoenolpyruvate analogs on the activity of enoylpyruvate transferase and the effect of UDP-N-acetylglucosamine on the reactivity of the active site SH group

1980

Anwar, R.A.; Vlaovic, M.

Biochim. Biophys. Acta

616

389-394

637595

7608103

MurA (MurZ), the enzyme that catalyzes the first committed step in peptidoglycan biosynthesis, is essential in Escherichia coli

1995

Brown, E.D.; Vivas, E.I.; Walsh, C.T.; Kolter, R.

J. Bacteriol.

177

4194-4197

637596

-

Stereochemical analysis of the tetrahedral adduct formed at the active site of UDP-GlcNAc enolpyruvyl transferase from the pseudosubstrates, (E)- and (Z)-3-fluorophosphoenolpyruvate, in D2O

1995

Kim, D.H.; Lees, W.J.; Walsh, C.T.

J. Am. Chem. Soc.

117

6380-6381

637597

-

Kinetic characterization of the inactivation of UDP-GlcNAc enolpyruvyl transferase by (Z)-3-fluorophosphoenolpyruvate: evidence for two oxocarbenium ion intermediates in enolpyruvyl transfer catalysis

1995

Kim, D.H.; Lees, W.J.; Haley, T.M.; Walsh, C.T.

J. Am. Chem. Soc.

117

1494-1502

637598

8664284

Characterization of a Cys115 to Asp substitution in the Escherichia coli cell wall biosynthetic enzyme UDP-GlcNAc enolpyruvyl transferase (MurA) that confers resistance to inactivation by the antibiotic fosfomycin

1996

Kim, D.H.; Lees, W.J.; Kempsell, K.E.; Lane, W.S.; Duncan, K.; Walsh, C.T.

Biochemistry

35

4923-4928

637599

8994972

Structure of UDP-N-acetylglucosamine enolpyruvyl transferase, and enzyme essential for the synthesis of bacterial peptidoglycan, complexed with substrate UDP-N-acetylglucosamine and the drug fosfomycin

1996

Skarzynski, T.; Mistry, A.; Wonacott, A.; Hutchinson, S.E.; Kelly, V.A.; Duncan, K.

Structure

4

1465-1474

637600

8805592

Crystal structure of UDP-N-acetylglucosamine enolpyruvyltransferase, the target of the antibiotic fosfomycin

1996

Schoenbrunn, E.; Sack, S.; Eschenburg, S.; Perrakis, A.; Krekel, F.; Amrhein, N.; Mandelkow, E.

Structure

4

1065-1075

637601

9654090

Studies on the conformational changes in the bacterial cell wall biosynthetic enzyme UDP-N-acetylglucosamine enolpyruvyltransferase (MurA)

1998

Schonbrunn, E.; Svergun, D.I.; Amrhein, N.; Koch, M.H.J.

Eur. J. Biochem.

253

406-412

637602

10413459

Substrate and inhibitor-induced conformational changes in the structurally related enzymes UDP-N-acetylglucosamine enolpyruvyl transferase (MurA) and 5-enolpyruvylshikimate 3-phosphate synthase (EPSPS)

1999

Krekel, F.; Oecking, C.; Amrhein, N.; Macheroux, P.

Biochemistry

38

8864-8878

637603

10529188

Lysine 22 in UDP-N-acetylglucosamine enolpyruvyl transferase from Enterobacter cloacae is crucial for enzymatic activity and the formation of covalent adducts with the substrate phosphoenolpyruvate and the antibiotic fosfomycin

1999

Samland, A.K.; Amrhein, N.; Macheroux, P.

Biochemistry

38

13162-13169

637604

10894720

Two active forms of UDP-N-acetylglucosamine enolpyruvyl transferase in gram-positive bacteria

2000

Du, W.; Brown, J.R.; Sylvester, D.R.; Huang, J.; Chalker, A.F.; So, C.Y.; Holmes, D.J.; Payne, D.J.; Wallis, N.G.

J. Bacteriol.

182

4146-4152

637605

11027147

Determination of the pKa value of C115 in MurA (UDP-N-acetylglucosamine enolpyruvyltransferase) from Enterobacter cloacae

2000

Krekel, F.; Samland, A.K.; Macheroux, P.; Amrhein, N.; Evans, J.N.S.

Biochemistry

39

12671-12677

637606

11820287

Characterization and inhibition study of MurA enzyme by capillary electrophoresis

2002

Dai, H.J.; Parker, C.N.; Bao, J.J.

J. Chromatogr. B

766

123-132

637607

11502190

Thermodynamic characterization of ligand-induced conformational changes in UDP-N-acetylglucosamine enolpyruvyl transferase

2001

Samland, A.K.; Jelesarov, I.; Kuhn, R.; Amrhein, N.; Macheroux, P.

Biochemistry

40

9950-9956

637608

11327813

Asparagine 23 and aspartate 305 are essential residues in the active site of UDP-N-acetylglucosamine enolpyruvyl transferase from Enterobacter cloacae

2001

Samland, A.K.; Etezady-Esfarjani, T.; Amrhein, N.; Macheroux, P.

Biochemistry

40

1550-1559

637609

12562791

In vitro and in vivo functional activity of Chlamydia MurA, a UDP-N-acetylglucosamine enolpyruvyl transferase involved in peptidoglycan synthesis and fosfomycin resistance

2003

McCoy, A.J.; Sandlin, R.C.; Maurelli, A.T.

J. Bacteriol.

185

1218-1228

655618

12757953

Isolation and mutation site determination of the temperature-sensitive murB mutants of Staphylococcus aureus

2003

Matsuo, M.; Kurokawa, K.; Nishida, S.; Li, Y.; Takimura, H.; Kaito, C.; Fukuhara, N.; Maki, H.; Miura, K.; Murakami, K.; Sekimizu, K.

FEMS Microbiol. Lett.

222

107-113

669466

16236703

Identification and characterization of amino acid residues essential for the active site of UDP-N-acetylenolpyruvylglucosamine reductase (MurB) from Staphylococcus aureus

2006

Nishida, S.; Kurokawa, K.; Matsuo, M.; Sakamoto, K.; Ueno, K.; Kita, K.; Sekimizu, K.

J. Biol. Chem.

281

1714-1724

669810

17004716

Pyrazolidine-3,5-diones and 5-hydroxy-1H-pyrazol-3(2H)-ones, inhibitors of UDP-N-acetylenolpyruvyl glucosamine reductase

2006

Gilbert, A.M.; Failli, A.; Shumsky, J.; Yang, Y.; Severin, A.; Singh, G.; Hu, W.; Keeney, D.; Petersen, P.J.; Katz, A.H.

J. Med. Chem.

49

6027-6036

689925

17120230

Crystal structure of UDP-N-acetylenolpyruvylglucosamine reductase (MurB) from Thermus caldophilus

2007

Kim, M.; Cho, M.K.; Song, H.; Kim, D.; Park, B.; Lee, J.H.; Kang, G.B.; Kim, S.H.; Im, Y.J.; Lee, D.; Eom, S.H.

Proteins

66

751-754

698345

-

In silico structural characterization of Mycobacterium tuberculosis H37Rv UDP-N-acetylmuramate dehydrogenase

2009

Babajan, B.; Anuradha, C.; Chaitanya, M.; Gowsia, D.; Kumar, C.

Int. J. Integr. Biol.

6

12-16

722410

-

Structural and functional features of UDP-N-acetylenolpyruvylglucosamine reductase of Mycobacterium tuberculosis H37Rv

2010

Gautam, A.; Shukla, H.; Khan, S.; Rishi, P.; Bhakuni, V.; Tewari, R.

Int. J. Integr. Biol.

10

66-75

722831

22068704

A homogeneous, high-throughput-compatible, fluorescence intensity-based assay for UDP-N-acetylenolpyruvylglucosamine reductase (MurB) with nanomolar product detection

2012

Shapiro, A.B.; Livchak, S.; Gao, N.; Whiteaker, J.; Thresher, J.; Jahic, H.; Huang, J.; Gu, R.F.

J. Biomol. Screen.

17

327-338

723008

20614148

Identification of hotspot regions of MurB oxidoreductase enzyme using homology modeling, molecular dynamics and molecular docking techniques

2011

Kumar, V.; Saravanan, P.; Arvind, A.; Mohan, C.G.

J. Mol. Model.

17

939-953

744976

27047475

Identification and partial characterization of a novel UDP-N-acetylenolpyruvoylglucosamine reductase/UDP-N-acetylmuramate L-alanine ligase fusion enzyme from Verrucomicrobium spinosum DSM 4136(T)

2016

Naqvi, K.F.; Patin, D.; Wheatley, M.S.; Savka, M.A.; Dobson, R.C.; Gan, H.M.; Barreteau, H.; Blanot, D.; Mengin-Lecreulx, D.; Hudson, A.O.

Front. Microbiol.

7

362

746242

23805286

Substrate channel flexibility in Pseudomonas aeruginosa MurB accommodates Two distinct substrates

2013

Chen, M.W.; Lohkamp, B.; Schnell, R.; Lescar, J.; Schneider, G.

PLoS ONE

8

e66936

Ligand UDP-N-acetyl-3-O-(1-carboxyvinyl)-alpha-D-glucosamine

Basic Ligand Information

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (4 results)

In Vivo Product in Enzyme-catalyzed Reactions (24 results)

Substrate in Enzyme-catalyzed Reactions (6 results)

Product in Enzyme-catalyzed Reactions (32 results)

Inhibitor in Enzyme-catalyzed Reactions (1 result)

3D Structure of Enzyme-Ligand-Complex (PDB) (67 results)

Enzyme Kinetic Parameters

K_M Value (7 results)

References & Links

Literature References (44)

Links to other databases for UDP-N-acetyl-3-O-(1-carboxyvinyl)-alpha-D-glucosamine

Ligand UDP-N-acetyl-3-O-(1-carboxyvinyl)-alpha-D-glucosamine

Basic Ligand Information

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (4 results)

In Vivo Product in Enzyme-catalyzed Reactions (24 results)

Substrate in Enzyme-catalyzed Reactions (6 results)

Product in Enzyme-catalyzed Reactions (32 results)

Inhibitor in Enzyme-catalyzed Reactions (1 result)

3D Structure of Enzyme-Ligand-Complex (PDB) (67 results)

Enzyme Kinetic Parameters

KM Value (7 results)

References & Links

Literature References (44)

Links to other databases for UDP-N-acetyl-3-O-(1-carboxyvinyl)-alpha-D-glucosamine

K_M Value (7 results)