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Ligand GlcNAc-(1->4)-Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphosphoundecaprenol

Basic Ligand Information

Molecular Structure

Show all BRENDA pathways known for GlcNAc-(1->4)-Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphosphoundecaprenol

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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

2.4.1.129

[GlcNAc-(1-4)-Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)]n-diphosphoundecaprenol + GlcNAc-(1-4)-Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphosphoundecaprenol = [GlcNAc-(1-4)-Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)]n+1-diphosphoundecaprenol + undecaprenyl diphosphate

706885, 488532, 488533, 488536, 674265

-

2.4.1.129

[GlcNAc-(1->4)-Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)]n-diphosphoundecaprenol + GlcNAc-(1->4)-Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphosphoundecaprenol = [GlcNAc-(1->4)-Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)]n+1-diphosphoundecaprenol + undecaprenyl diphosphate

758865, 759785, 758901, 759728, 759431, 735922

-

6.3.5.13

ATP + beta-D-GlcNAc-(1->4)-Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphospho-ditrans,octacis-undecaprenol + L-glutamine + H2O = ADP + phosphate + beta-D-GlcNAc-(1->4)-MurNAc-L-Ala-D-isoglutaminyl-L-Lys-D-Ala-D-Ala-diphospho-ditrans,octacis-undecaprenol + L-glutamate

751671, 752003

-

6.3.5.13

ATP + beta-D-GlcNAc-(1->4)-Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphospho-ditrans,octacis-undecaprenol = ADP + beta-D-GlcNAc-(1->4)-MurNAc-L-Ala-gamma-D-O-P-Glu-L-Lys-D-Ala-D-Ala-diphospho-ditrans,octacis-undecaprenol

752003

-

2.4.1.129

2 entries

6.3.5.13

2 entries

In Vivo Product in Enzyme-catalyzed Reactions (2 results)

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Show Natural Product (2 entries)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

2.4.1.227

UDP-N-acetylglucosamine + Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphosphoundecaprenol = UDP + GlcNAc-(1-4)-Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphosphoundecaprenol

0

-

2.4.1.227

UDP-N-acetylglucosamine + Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphosphoundecaprenol = UDP + GlcNAc-(1->4)-Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphosphoundecaprenol

0

-

2.4.1.227

2 entries

Substrate in Enzyme-catalyzed Reactions (5 results)

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Show Substrate (5 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

2.3.2.B1

ditrans,ocatacis-undecaprenyl diphosphoryl (GlcNAc-beta-(1->4))MurNAc-L-alanyl-gamma-D-glutamyl-L-lysyl-D-alanyl-D-alanine + L-Ala-tRNa = ditrans,ocatacis-undecaprenyl diphosphoryl (GlcNAc-beta-(1->4))MurNAc-L-alanyl-gamma-D-glutamyl-L-lysyl(N6-L-alanyl)-D-alanyl-D-alanine + tRNA

711438

-

2.4.1.129

[GlcNAc-(1-4)-Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)]n-diphosphoundecaprenol + GlcNAc-(1-4)-Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphosphoundecaprenol = [GlcNAc-(1-4)-Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)]n+1-diphosphoundecaprenol + undecaprenyl diphosphate

488533, 703349, 705123, 488532, 488534, 488535, 704276, 704207, 706885, 701437, 706545, 704163, 488531, 488536, 674265, 671367, 672145

-

2.4.1.129

[GlcNAc-(1->4)-Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)]n-diphosphoundecaprenol + GlcNAc-(1->4)-Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphosphoundecaprenol = [GlcNAc-(1->4)-Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)]n+1-diphosphoundecaprenol + undecaprenyl diphosphate

758865, 759785, 758901, 759728, 759431, 735922

-

6.3.5.13

ATP + beta-D-GlcNAc-(1->4)-Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphospho-ditrans,octacis-undecaprenol + L-glutamine + H2O = ADP + phosphate + beta-D-GlcNAc-(1->4)-MurNAc-L-Ala-D-isoglutaminyl-L-Lys-D-Ala-D-Ala-diphospho-ditrans,octacis-undecaprenol + L-glutamate

751671, 752003

-

6.3.5.13

ATP + beta-D-GlcNAc-(1->4)-Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphospho-ditrans,octacis-undecaprenol = ADP + beta-D-GlcNAc-(1->4)-MurNAc-L-Ala-gamma-D-O-P-Glu-L-Lys-D-Ala-D-Ala-diphospho-ditrans,octacis-undecaprenol

752003

-

2.4.1.129

2 entries

6.3.5.13

2 entries

Product in Enzyme-catalyzed Reactions (2 results)

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Show Product (2 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

2.4.1.227

UDP-N-acetylglucosamine + Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphosphoundecaprenol = UDP + GlcNAc-(1-4)-Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphosphoundecaprenol

0

-

2.4.1.227

UDP-N-acetylglucosamine + Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphosphoundecaprenol = UDP + GlcNAc-(1->4)-Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphosphoundecaprenol

0

-

2.4.1.227

2 entries

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

6.3.5.13

4

-

pH 7.5, 30°C

751671

K_M Value (3 results)

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Show KM Value (3 entries)

EC NUMBER

KM VALUE [MM]

KM VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

2.4.1.129

0.002

-

lipid II, pH 7.5, 25°C

735922

2.4.1.129

0.002

-

lipid II, pH 8.0, 20°C

735922

2.4.1.129

2 entries

6.3.5.13

0.22

-

pH 7.5, 30°C

751671

References & Links

Literature References (26)

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Show Reference (26 entries)

BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

488531

6802846

Purification of the peptidoglycan transglycosylase of Bacillus megaterium

1982

Taku, A.; Stuckey, M.; Fan, D.P.

J. Biol. Chem.

257

5018-5022

488532

7030331

Peptidoglycan synthetic enzyme activities of highly purified penicillin-binding protein 3 in Escherichia coli: a septum-forming reaction sequence

1981

Ishino, F.; Matsuhashi, M.

Biochem. Biophys. Res. Commun.

101

905-911

488533

6693351

Staphylococcus aureus and Micrococcus luteus peptidoglycan transglycosylases that are not penicillin-binding proteins

1984

Park, W.; Matsuhashi, M.

J. Bacteriol.

157

538-544

488534

6389538

Functional biosynthesis of cell wall peptidoglycan by polymorphic bifunctional polypeptides. Penicillin-binding protein 1Bs of Escherichia coli with activities of transglycosylase and transpeptidase

1984

Nakagawa, J.; Tamaki, S.; Tomioka, S.; Matsuhashi, M.

J. Biol. Chem.

259

13937-13946

488535

-

Major peptidoglycan transglycosylase activity in Streptococcus pneumoniae that is not a penicillin-binding protein

1985

Park, W.; Seto, H.; Hakenbeck, R.; Matsuhashi, M.

FEMS Microbiol. Lett.

27

45-48

488536

11320055

Formation of the glycan chains in the synthesis of bacterial peptidoglycan

2001

Van Heijenoort, J.

Glycobiology

11

25R-36R

671367

16569861

Screen for inhibitors of the coupled transglycosylase-transpeptidase of peptidoglycan biosynthesis in Escherichia coli

2006

Ramachandran, V.; Chandrakala, B.; Kumar, V.P.; Usha, V.; Solapure, S.M.; de Sousa, S.M.

Antimicrob. Agents Chemother.

50

1425-1432

672145

16548528

Glycosyl transferase activity of the Escherichia coli penicillin-binding protein 1b: specificity profile for the substrate

2006

Fraipont, C.; Sapunaric, F.; Zervosen, A.; Auger, G.; Devreese, B.; Lioux, T.; Blanot, D.; Mengin-Lecreulx, D.; Herdewijn, P.; van Beeumen, J.; Frere, J.M.; Nguyen-Disteche, M.

Biochemistry

45

4007-4013

674265

16484198

Characterization of the bifunctional glycosyltransferase/acyltransferase penicillin-binding protein 4 of Listeria monocytogenes

2006

Zawadzka-Skomial, J.; Markiewicz, Z.; Nguyen-Disteche, M.; Devreese, B.; Frere, J.M.; Terrak, M.

J. Bacteriol.

188

1875-1881

701437

18642800

Structural analysis of the contacts anchoring moenomycin to peptidoglycan glycosyltransferases and implications for antibiotic design

2008

Yuan, Y.; Fuse, S.; Ostash, B.; Sliz, P.; Kahne, D.; Walker, S.

ACS Chem. Biol.

3

429-436

703349

18721881

Structural details of the glycosyltransferase step of peptidoglycan assembly

2008

Lovering, A.L.; Gretes, M.; Strynadka, N.C.

Curr. Opin. Struct. Biol.

18

534-543

704163

18834124

Isolated peptidoglycan glycosyltransferases from different organisms produce different glycan chain lengths

2008

Wang, T.S.; Manning, S.A.; Walker, S.; Kahne, D.

J. Am. Chem. Soc.

130

14068-14069

704207

20017480

The role of the substrate lipid in processive glycan polymerization by the peptidoglycan glycosyltransferases

2010

Perlstein, D.; Wang, T.; Doud, E.; Kahne, D.; Walker, S.

J. Am. Chem. Soc.

132

48-49

704276

18165305

The monofunctional glycosyltransferase of Escherichia coli localizes to the cell division site and interacts with penicillin-binding protein 3, FtsW, and FtsN

2008

Derouaux, A.; Wolf, B.; Fraipont, C.; Breukink, E.; Nguyen-Disteche, M.; Terrak, M.

J. Bacteriol.

190

1831-1834

705123

18760285

Identification of dynamic structural motifs involved in peptidoglycan glycosyltransfer

2008

Lovering, A.L.; De Castro, L.; Strynadka, N.C.

J. Mol. Biol.

383

167-177

706545

19458048

Crystal structure of the membrane-bound bifunctional transglycosylase PBP1b from Escherichia coli

2009

Sung, M.T.; Lai, Y.T.; Huang, C.Y.; Chou, L.Y.; Shih, H.W.; Cheng, W.C.; Wong, C.H.; Ma, C.

Proc. Natl. Acad. Sci. USA

106

8824-8829

706885

18809265

The putative penicillin-binding proteins 1 and 2 are important for viability, growth and cell morphology of Brucella melitensis

2009

Bandara, A.; Schurig, G.; Sriranganathan, N.; Prasad, R.; Boyle, S.

Vet. Microbiol.

133

387-393

711438

19356937

Inhibition of tRNA-dependent ligase MurM from Streptococcus pneumoniae by phosphonate and sulfonamide inhibitors

2009

Cressina, E.; Lloyd, A.J.; De Pascale, G.; Mok, B.J.; Caddick, S.; Roper, D.I.; Dowson, C.G.; Bugg, T.D.H.

Bioorg. Med. Chem.

17

3443-3455

735922

26358369

Targeting bacterial cell wall peptidoglycan synthesis by inhibition of glycosyltransferase activity

2016

Mesleh, M.F.; Rajaratnam, P.; Conrad, M.; Chandrasekaran, V.; Liu, C.M.; Pandya, B.A.; Hwang, Y.S.; Rye, P.T.; Muldoon, C.; Becker, B.; Zuegg, J.; Meutermans, W.; Moy, T.I.

Chem. Biol. Drug Des.

87

190-199

751671

30093673

Structure of the essential peptidoglycan amidotransferase MurT/GatD complex from Streptococcus pneumoniae

2018

Morlot, C.; Straume, D.; Peters, K.; Hegnar, O.; Simon, N.; Villard, A.; Contreras-Martel, C.; Leisico, F.; Breukink, E.; Gravier-Pelletier, C.; Le Corre, L.; Vollmer, W.; Pietrancosta, N.; Havarstein, L.; Zapun, A.

Nat. Commun.

9

3180

752003

22291598

Identification and in vitro analysis of the GatD/MurT enzyme-complex catalyzing lipid II amidation in Staphylococcus aureus

2012

Muench, D.; Roemer, T.; Lee, S.H.; Engeser, M.; Sahl, H.G.; Schneider, T.

PLoS Pathog.

8

e1002509

758865

29909047

Peptidoglycan glycosyltransferase-ligand binding assay based on tryptophan fluorescence quenching

2018

Dahmane, I.; Montagner, C.; Matagne, A.; Dumbre, S.; Herdewijn, P.; Terrak, M.

Biochimie

152

1-5

758901

32146179

Hydrophobic substituents on isatin derivatives enhance their inhibition against bacterial peptidoglycan glycosyltransferase activity

2020

Wang, Y.; Cheong, W.L.; Liang, Z.; So, L.Y.; Chan, K.F.; So, P.K.; Chen, Y.W.; Wong, W.L.; Wong, K.Y.

Bioorg. Chem.

97

103710

759431

30322854

Inactivation of the monofunctional peptidoglycan glycosyltransferase SgtB allows Staphylococcus aureus to survive in the absence of lipoteichoic acid

2019

Karinou, E.; Schuster, C.F.; Pazos, M.; Vollmer, W.; Gruendling, A.

J. Bacteriol.

201

e00574-18

759728

27311672

Continuous fluorescence assay for peptidoglycan glycosyltransferases

2016

Egan, A.J.; Vollmer, W.

Methods Mol. Biol.

1440

171-184

759785

26933838

Suppression of a deletion mutation in the gene encoding essential PBP2b reveals a new lytic transglycosylase involved in peripheral peptidoglycan synthesis in Streptococcus pneumoniae D39

2016

Tsui, H.C.; Zheng, J.J.; Magallon, A.N.; Ryan, J.D.; Yunck, R.; Rued, B.E.; Bernhardt, T.G.; Winkler, M.E.

Mol. Microbiol.

100

1039-1065

Links to other databases for GlcNAc-(1->4)-Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphosphoundecaprenol

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