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Ligand UDP-N-acetylmuramoyl-L-Ala-D-Glu

Basic Ligand Information

Molecular Structure

Show all BRENDA pathways known for UDP-N-acetylmuramoyl-L-Ala-D-Glu

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Roles as Enzyme Ligand

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

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Show Natural Substrate (4 entries)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

6.3.2.13

ATP + UDP-N-acetylmuramoyl-L-alanyl-D-glutamate + meso-2,6-diaminoheptanedioate = ADP + phosphate + UDP-N-acetylmuramoyl-L-alanyl-D-gamma-glutamyl-meso-2,6-diamino-heptanedioate

651110, 645342, 653141, 652097

-

6.3.2.13

ATP + UDP-N-acetylmuramoyl-L-alanyl-D-glutamate + meso-2,6-diaminoheptanedioate = ADP + phosphate + UDP-N-acetylmuramoyl-L-alanyl-D-gamma-glutamyl-meso-2,6-diaminoheptanedioate

728598, 715975

-

6.3.2.7

ATP + UDP-N-acetylmuramoyl-L-Ala-D-Glu + L-Lys = ?

1270

-

6.3.2.7

ATP + UDP-N-acetylmuramoyl-L-alanyl-D-glutamate + L-lysine = ADP + phosphate + UDP-N-acetylmuramoyl-L-alanyl-D-glutamyl-L-lysine

726560, 727964

-

6.3.2.13

2 entries

6.3.2.7

2 entries

In Vivo Product in Enzyme-catalyzed Reactions (1 result)

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Show Natural Product (1 entry)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

6.3.2.9

ATP + UDP-N-acetylmuramyl-L-alanine + D-glutamate = ADP + phosphate + UDP-N-acetylmuramoyl-L-alanyl-D-glutamate

0

-

Substrate in Enzyme-catalyzed Reactions (14 results)

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Show Substrate (14 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

6.3.2.13

ATP + UDP-N-acetylmuramoyl-L-Ala-D-Glu + meso-diaminopimelic acid = ADP + phosphate + UDP-N-acetylmuramoyl-L-Ala-D-Glu-meso-diaminopimelic acid

716979

-

6.3.2.13

ATP + UDP-N-acetylmuramoyl-L-alanyl-D-glutamate + D-lysine = ADP + phosphate + UDP-N-acetylmuramoyl-L-alanyl-D-gamma-glutamyl-D-lysine

674565

-

6.3.2.13

ATP + UDP-N-acetylmuramoyl-L-alanyl-D-glutamate + L-lysine = ADP + phosphate + UDP-N-acetylmuramoyl-L-alanyl-D-gamma-glutamyl-L-lysine

677175, 674565

-

6.3.2.13

ATP + UDP-N-acetylmuramoyl-L-alanyl-D-glutamate + L-ornithine = ADP + phosphate + UDP-N-acetylmuramoyl-L-alanyl-D-gamma-glutamyl-L-ornithine

674565

-

6.3.2.13

ATP + UDP-N-acetylmuramoyl-L-alanyl-D-glutamate + meso-2,6-diaminoheptanedioate = ADP + phosphate + UDP-N-acetylmuramoyl-L-alanyl-D-gamma-glutamyl-meso-2,6-diamino-heptanedioate

653141, 651110, 674330, 645342, 652097

-

6.3.2.13

ATP + UDP-N-acetylmuramoyl-L-alanyl-D-glutamate + meso-2,6-diaminoheptanedioate = ADP + phosphate + UDP-N-acetylmuramoyl-L-alanyl-D-gamma-glutamyl-meso-2,6-diaminoheptanedioate

728598, 715975

-

6.3.2.13

ATP + UDP-N-acetylmuramoyl-L-alanyl-D-glutamate + meso-diaminopimelic acid = ADP + phosphate + UDP-N-acetylmuramoyl-L-alanyl-D-gamma-glutamyl-meso-diaminopimelic acid

674565

-

6.3.2.13

UDP-N-acetylmuramoyl-L-alanyl-D-glutamate + ATP + meso-diaminopimelic acid = ADP + phosphate + UDP-N-acetylmuramoyl-L-alanyl-D-gamma-glutamyl-meso-diaminopimelic acid

715309, 702135

-

6.3.2.37

UDP-N-acetylmuramoyl-L-Ala-D-Glu + D-Lys + ATP = UDP-N-acetylmuramoyl-L-Ala-D-Glu-D-Lys + ADP + phosphate

674565

-

6.3.2.37

UDP-N-acetylmuramoyl-L-Ala-D-Glu + L-Lys + ATP = UDP-N-acetylmuramoyl-L-Ala-D-Glu-L-Lys + ADP + phosphate

674565

-

6.3.2.37

UDP-N-acetylmuramoyl-L-Ala-D-Glu + meso-diaminopimelic acid + ATP = UDP-N-acetylmuramoyl-L-Ala-D-Glu-meso-diaminopimelic acid + ADP + phosphate

674565

-

6.3.2.7

ATP + UDP-N-acetylmuramoyl-L-Ala-D-Glu + L-Lys = ?

1270

-

6.3.2.7

ATP + UDP-N-acetylmuramoyl-L-Ala-D-Glu + L-Lys = ADP + phosphate + UDP-N-acetylmuramoyl-L-Ala-D-Glu-L-Lys

1273, 1274, 1275, 671656, 714367, 985, 1033, 1270, 661609

-

6.3.2.7

ATP + UDP-N-acetylmuramoyl-L-alanyl-D-glutamate + L-lysine = ADP + phosphate + UDP-N-acetylmuramoyl-L-alanyl-D-glutamyl-L-lysine

726560, 727964

-

6.3.2.13

8 entries

6.3.2.37

3 entries

6.3.2.7

3 entries

Product in Enzyme-catalyzed Reactions (6 results)

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Show Product (6 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

6.3.2.45

ATP + UDP-N-alpha-D-acetylmuramate + L-Ala-D-Glu = ADP + phosphate + UDP-N-acetylmuramoyl-L-Ala-D-Glu

0

-

6.3.2.9

ATP + UDP-N-acetylmuramoyl-L-Ala + D-Glu = ADP + phosphate + UDP-N-acetylmuramoyl-L-Ala-D-Glu

0

-

6.3.2.9

ATP + UDP-N-acetylmuramoyl-L-Ala + Glu = ADP + phosphate + UDP-N-acetylmuramoyl-L-Ala-D-Glu

0

-

6.3.2.9

ATP + UDP-N-acetylmuramate-L-alanine + D-glutamate = ADP + phosphate + UDP-N-acetylmuramoyl-L-alanyl-D-glutamate

0, 649861

-

6.3.2.9

ATP + UDP-N-acetylmuramyl-L-alanine + D-glutamate = ADP + phosphate + UDP-N-acetylmuramoyl-L-alanyl-D-glutamate

0

-

6.3.2.9

4 entries

6.3.2.B2

ATP + L-alanyl-gamma-D-glutamate + UDP-MurNAc = ADP + phosphate + UDP-N-acetylmuramoyl-L-alanyl-gamma-D-glutamate

0

-

Inhibitor in Enzyme-catalyzed Reactions (5 results)

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Show Inhibitors (5 entries)

EC NUMBER

COMMENTARY

LITERATURE

ENZYME 3D STRUCTURE

2.5.1.7

no inhibition

637591

-

2.5.1.7

weak

637590

-

2.5.1.7

2 entries

6.3.2.37

strong inhibition by excess UDP-N-acetylmuramoyl-L-Ala-D-Glu is observed

674565

-

6.3.2.7

above 10 mM

1275

-

6.3.2.9

-

1276, 1293

-

Enzyme Kinetic Parameters

k_cat Value (Turnover Number) (1 result)

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Show Turnover Number (1 entry)

EC NUMBER

TURNOVER NUMBER [1/S]

TURNOVER NUMBER MAXIMUM [1/S]

COMMENTARY

LITERATURE

6.3.2.7

9

-

23°C

661609

K_M Value (8 results)

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Show KM Value (8 entries)

EC NUMBER

KM VALUE [MM]

KM VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

6.3.2.13

0.03

-

-

702135

6.3.2.13

0.04

-

pH 7.4, 37°C

716979

6.3.2.13

0.45

-

at 68°C

674565

6.3.2.7

0.087

-

pH 8.6, 37°C

714367

6.3.2.7

0.122

-

23°C

661609

6.3.2.7

0.53

-

in presence of 30 mM K2HPO4

1270

6.3.2.7

0.57

-

in presence of 2 mM K2HPO4

1270

6.3.2.7

0.59

-

in presence of 60 mM KCl

1270

6.3.2.13

3 entries

6.3.2.7

5 entries

References & Links

Literature References (28)

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Show Reference (28 entries)

BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

985

4417383

Cell wall polymers of Bacillus sphaericus: activities of enzymes involved in peptidoglycan precursor synthesis during sporulation

1974

Linnett, P.E.; Tipper, D.J.

J. Bacteriol.

120

342-354

1033

1262302

Distribution of peptidoglycan synthetase activities between sporangia and forespores in sporulating cells of Bacillus sphaericus

1976

Tipper, D.J.; Linnett, P.E.

J. Bacteriol.

126

213-221

1270

3718704

UDP-N-acetylmuramoyl-L-alanyl-D-glutamyl-L-lysine synthetase from Bacillus sphaericus: activation by potassium phosphate

1986

Anwar, R.A.; Vlaovic, M.

Biochem. Cell Biol.

64

297-303

1273

4669213

Regulation of the bacterial cell wall: isolation and characterization of peptidoglycan mutants of Staphylococcus aureus

1972

Chatterjee, A.N.; Young, F.E.

J. Bacteriol.

111

220-230

1274

4669214

Conditional mutants of Staphylococcus aureus defective in cell wall precursor synthesis

1972

Good, C.M.; Tipper, D.J.

J. Bacteriol.

111

231-241

1275

-

Enzymatic synthesis of the peptide in bacterial uridine nucleotides. I. Enzymatic addition of L-alanine, D-glutamic acid, and L-lysine

1962

Ito, E.; Strominger, J.L.

J. Biol. Chem.

237

2689-2695

1276

6125497

Cytoplasmic steps of peptidoglycan synthesis in Escherichia coli

1982

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

J. Bacteriol.

151

1109-1117

1293

3301347

Partial purification and specificity studies of the D-glutamate-adding and D-alanyl-D-alanine-adding enzymes from Escherichia coli K12

1987

Michaud, C.; Blanot, D.; Flouret, B.; van Heijenoort, J.

Eur. J. Biochem.

166

631-637

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

645342

11281713

The cell wall and cell division gene cluster in the Mra operon of Pseudomonas aeruginosa: Cloning, production, and purification of active enzymes

2001

Azzolina, B.A.; Yuan, X.; Anderson, M.S.; El-Sherbeini, M.

Protein Expr. Purif.

21

393-400

649861

10493791

Role of the ortholog and paralog amino acid invariants in the active site of the UDP-MurNAc-L-alanine:D-glutamate ligase (MurD)

1999

Bouhss, A.; Dementin, S.; Parquet, C.; Mengin-Lecreulx, D.; Bertrand, J.A.; Le Beller, D.; Dideberg, O.; van Heijenoort, J.; Blanot, D.

Biochemistry

38

12240-12247

651110

11722566

Evidence of a functional requirement for a carbamoylated lysine residue in MurD, MurE and MurF synthetases as established by chemical rescue experiments

2001

Dementin, S.; Bouhss, A.; Auger, G.; Parquet, C.; Mengin-Lecreulx, D.; Dideberg, O.; van Heijenoort, J.; Blanot, D.

Eur. J. Biochem.

268

5800-5807

652097

11124264

Crystal structure of UDP-N-acetylmuramoyl-L-alanyl-D-glutamate:meso-diaminopimelate ligase from Escherichia coli

2001

Gordon, E.; Flouret, B.; Chantalat, L.; van Heijenoort, J.; Mengin-Lecreulx, D.; Dideberg, O.

J. Biol. Chem.

276

10999-11006

653141

9650993

Molecular cloning and DNA sequencing of the Staphylococcus aureus UDP-N-acetylmuramyl tripeptide synthetase (murE) gene, essential for the optimal expression of methicillin resistance

1998

Ludovice, A.M.; Wu, S.W.; de Lencastre, H.

Microb. Drug Resist.

4

85-90

661609

-

Cloning, expression and characterization of the Streptococcus pyogenes murE gene encoding a UDP-MurNAc-L-alanyl-D-glutamate: L-lysine ligase

2004

Triolo, T.A.; Chabin, R.M.; Pompliano, D.L.

Enzyme Microb. Technol.

35

300-308

671656

17335103

Phosphinate inhibitors of UDP-N-acetylmuramoyl-L-alanyl-D-glutamate: L-lysine ligase (MurE)

2007

Strancar, K.; Boniface, A.; Blanot, D.; Gobec, S.

Arch. Pharm.

340

127-134

674330

17384195

Biochemical characterization and physiological properties of Escherichia coli UDP-N-acetylmuramate:L-alanyl-gamma-D-glutamyl-meso-diaminopimelate ligase

2007

Herve, M.; Boniface, A.; Gobec, S.; Bianot, D.; Mengin-Lecreulx, D.

J. Bacteriol.

189

3987-3995

674565

16595662

The MurE synthetase from Thermotoga maritima is endowed with an unusual D-lysine adding activity

2006

Boniface, A.; Bouhss, A.; Mengin-Lecreulx, D.; Blanot, D.

J. Biol. Chem.

281

15680-15686

677175

-

A new approach towards peptidosulfonamides: synthesis of potential inhibitors of bacterial peptidoglycan biosynthesis enzymes MurD and MurE

2006

Humljan, J.; Kotnik, M.; Boniface, A.; Solmajer, T.; Urleb, U.; Blanot, D.; Gobec, S.

Tetrahedron

62

10980-10988

702135

19400768

Pseudomonas aeruginosa MurE amide ligase: enzyme kinetics and peptide inhibitor

2009

Paradis-Bleau, C.; Lloyd, A.; Sanschagrin, F.; Maaroufi, H.; Clarke, T.; Blewett, A.; Dowson, C.; Roper, D.I.; Bugg, T.D.; Levesque, R.C.

Biochem. J.

421

263-272

714367

20659527

Purification and biochemical characterization of Mur ligases from Staphylococcus aureus

2010

Patin, D.; Boniface, A.; Kovac, A.; Hervé, M.; Dementin, S.; Barreteau, H.; Mengin-Lecreulx, D.; Blanot, D.

Biochimie

92

1793-1800

715309

21622974

Interaction of N-methyl-2-alkenyl-4-quinolones with ATP-dependent MurE ligase of Mycobacterium tuberculosis: antibacterial activity, molecular docking and inhibition kinetics

2011

Guzman, J.D.; Wube, A.; Evangelopoulos, D.; Gupta, A.; Huefner, A.; Basavannacharya, C.; Rahman, M.M.; Thomaschitz, C.; Bauer, R.; McHugh, T.D.; Nobeli, I.; Prieto, J.M.; Gibbons, S.; Bucar, F.; Bhakta, S.

J. Antimicrob. Chemother.

66

1766-1772

715975

21491188

Comparative modeling of UDP-N-acetylmuramoyl-glycyl-D-glutamate-2,6-diaminopimelate ligase from Mycobacterium leprae and analysis of its binding features through molecular docking studies

2012

Shanmugam, A.; Natarajan, J.

J. Mol. Model.

18

115-125

716979

19945347

ATP-dependent MurE ligase in Mycobacterium tuberculosis: Biochemical and structural characterisation

2010

Basavannacharya, C.; Robertson, G.; Munshi, T.; Keep, N.; Bhakta, S.

Tuberculosis

90

16-24

726560

24061949

Design and synthesis of new peptidomimetics as potential inhibitors of MurE

2011

Zivec, M.; Turk, S.; Blanot, D.; Gobec, S.

Acta Chim. Slov.

58

95-109

727964

24064214

Specificity determinants for lysine incorporation in Staphylococcus aureus peptidoglycan as revealed by the structure of a MurE enzyme ternary complex

2013

Ruane, K.M.; Lloyd, A.J.; Fueloep, V.; Dowson, C.G.; Barreteau, H.; Boniface, A.; Dementin, S.; Blanot, D.; Mengin-Lecreulx, D.; Gobec, S.; Dessen, A.; Roper, D.I.

J. Biol. Chem.

288

33439-33448

728598

23555903

Characterisation of ATP-dependent Mur ligases involved in the biogenesis of cell wall peptidoglycan in Mycobacterium tuberculosis

2013

Munshi, T.; Gupta, A.; Evangelopoulos, D.; Guzman, J.D.; Gibbons, S.; Keep, N.H.; Bhakta, S.

PLoS ONE

8

e60143

Links to other databases for UDP-N-acetylmuramoyl-L-Ala-D-Glu

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ChEBI

PubChem