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Ligand N-acetyl-alpha-D-glucosaminyl-diphospho-ditrans,octacis-undecaprenol

Basic Ligand Information

Molecular Structure

Related pathways

Pathway Source

Pathways

BRENDA

O-antigen biosynthesis, teichoic acid biosynthesis

KEGG

Teichoic acid biosynthesis

MetaCyc

enterobacterial common antigen biosynthesis, Escherichia coli serotype O:104 O antigen biosynthesis, Escherichia coli serotype O:107 O antigen biosynthesis, Escherichia coli serotype O:111/Salmonella enterica serotype O:35 O antigen biosynthesis, Escherichia coli serotype O:117 O antigen biosynthesis, Escherichia coli serotype O:127 O antigen biosynthesis, Escherichia coli serotype O:128 O antigen biosynthesis, Escherichia coli serotype O:149/Shigella boydii serotype O1 O antigen biosynthesis, Escherichia coli serotype O:15 O antigen biosynthesis, Escherichia coli serotype O:152 O antigen biosynthesis, Escherichia coli serotype O:157/Salmonella enterica serotype O:30 O antigen biosynthesis, Escherichia coli serotype O:169 O antigen biosynthesis, Escherichia coli serotype O:177 O antigen biosynthesis, Escherichia coli serotype O:183/Shigella boydii serotype O:10 O antigen biosynthesis, Escherichia coli serotype O:1B/Salmonella enterica serotype O:42 O antigen biosynthesis, Escherichia coli serotype O:2 O antigen biosynthesis, Escherichia coli serotype O:21/Salmonella enterica serotype O:38 O antigen biosynthesis, Escherichia coli serotype O:49 O antigen biosynthesis, Escherichia coli serotype O:50 O antigen biosynthesis, Escherichia coli serotype O:51/Salmonella enterica serotype O:57 O antigen biosynthesis, Escherichia coli serotype O:52 O antigen biosynthesis, Escherichia coli serotype O:55/Salmonella enterica serotype O:50 O antigen biosynthesis, Escherichia coli serotype O:56 O antigen biosynthesis, Escherichia coli serotype O:7 O antigen biosynthesis, Escherichia coli serotype O:71/Salmonella enterica serotype O:28ac O antigen biosynthesis, Escherichia coli serotype O:77/Salmonella enterica serotype O:6,14 O antigen biosynthesis, Escherichia coli serotype O:8 O antigen biosynthesis, Escherichia coli serotype O:85/Salmonella enterica serotype O:17 O antigen biosynthesis, Escherichia coli serotype O:86 O antigen biosynthesis, Escherichia coli serotype O:9 O antigen biosynthesis, Escherichia coli serotype O:9a O antigen biosynthesis, H. pylori 26695 O-antigen biosynthesis, poly(3-O-beta-D-glucopyranosyl-N-acetylgalactosamine 1-phosphate) wall teichoic acid biosynthesis, poly(glycerol phosphate) wall teichoic acid biosynthesis, poly(ribitol phosphate) wall teichoic acid biosynthesis I (B. subtilis), poly(ribitol phosphate) wall teichoic acid biosynthesis II (S. aureus), Salmonella enterica serotype O:13 O antigen biosynthesis, Salmonella enterica serotype O:18 O antigen biosynthesis, Salmonella enterica serotype O:39 O antigen biosynthesis, Salmonella enterica serotype O:54 O antigen biosynthesis, Salmonella enterica serotype O:6,7 O antigen biosynthesis, Shigella boydii serotype 6 O antigen biosynthesis more

Show all BRENDA pathways known for N-acetyl-alpha-D-glucosaminyl-diphospho-ditrans,octacis-undecaprenol

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Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (9 results)

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Show Natural Substrate (9 entries)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

2.4.1.180

UDP-N-acetyl-D-mannosaminuronic acid + N-acetyl-D-glucosamine-diphosphorylundecaprenol + 2 H+ = UDP + ManNAcA-GlcNAc-diphosphorylundecaprenol + H2O

488808

-

2.4.1.187

UDP-N-acetylmannosamine + N-acetylglucosaminyl diphosphoryl-undecaprenol = UDP + N-acetyl-beta-D-mannosaminyl-1,4-N-acetyl-D-glucosaminyldiphosphoundecaprenol

488820, 704295

-

2.4.1.188

UDP-glucose + N-acetyl-D-glucosaminyldiphosphoundecaprenol = UDP + beta-D-glucosyl-1,4-N-acetyl-D-glucosaminyldiphosphoundecaprenol

488821

-

2.4.1.303

UDP-alpha-D-galactose + N-acetyl-alpha-D-glucosaminyl-diphospho-ditrans,octacis-undecaprenol = UDP + beta-D-Gal-beta-(1->3)-alpha-D-GlcNAc-diphospho-ditrans,octacis-undecaprenol

722373

-

2.4.1.304

UDP-alpha-D-galactose + N-acetyl-alpha-D-glucosaminyl-diphospho-ditrans,octacis-undecaprenol = UDP + beta-D-Gal-(1->4)-alpha-D-GlcNAc-diphospho-ditrans,octacis-undecaprenol

722531

-

2.4.1.305

UDP-alpha-D-glucose + N-acetyl-alpha-D-glucosaminyl-diphospho-ditrans,octacis-undecaprenol = UDP + beta-D-Glc-(1->3)-alpha-D-GlcNAc-diphospho-ditrans,octacis-undecaprenol

722520

-

2.4.1.343

UDP-alpha-D-galactose + N-acetyl-alpha-D-glucosaminyl-diphospho-ditrans,octacis-undecaprenol = UDP + alpha-D-Gal-(1->3)-alpha-D-GlcNAc-diphospho-ditrans,octacis-undecaprenol

740263

-

2.4.1.348

GDP-alpha-D-mannose + N-acetyl-alpha-D-glucosaminyl-diphospho-ditrans,octacis-undecaprenol = GDP + alpha-D-mannosyl-(1->3)-N-acetyl-alpha-D-glucosaminyl-diphospho-ditrans,octacis-undecaprenol

745286, 745287, 745794

-

5.1.3.26

N-acetyl-alpha-D-glucosaminyl-diphospho-ditrans,octacis-undecaprenol = N-acetyl-alpha-D-galactosaminyl-diphospho-ditrans,octacis-undecaprenol

722673

-

In Vivo Product in Enzyme-catalyzed Reactions (3 results)

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Show Natural Product (3 entries)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

2.7.8.13

UDP-N-acetyl-alpha-D-glucosamine + ditrans,octacis-undecaprenyl phosphate = UMP + N-acetyl-alpha-D-glucosaminyl-diphospho-ditrans,octacis-undecaprenol

-

-

2.7.8.33

UDP-N-acetyl-alpha-D-glucosamine + ditrans,octacis-undecaprenyl phosphate = UMP + N-acetyl-alpha-D-glucosaminyl-diphospho-ditrans,octacis-undecaprenol

-

-

2.7.8.33

UDP-N-acetyl-D-glucosamine + ditrans,polycis-undecaprenyl phosphate = UMP + N-acetyl-D-glucosaminyldiphospho-ditrans,polycis-undecaprenol

-

-

2.7.8.33

2 entries

Substrate in Enzyme-catalyzed Reactions (10 results)

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Show Substrate (10 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

2.4.1.180

UDP-N-acetyl-alpha-D-mannosaminuronate + N-acetyl-alpha-D-glucosaminyl-diphospho-ditrans,octacis-undecaprenol = UDP + N-acetyl-beta-D-mannosaminuronyl-(1->4)-N-acetyl-alpha-D-glucosaminyl-diphospho-ditrans,octacis-undecaprenol

721557

-

2.4.1.180

UDP-N-acetyl-D-mannosaminuronic acid + N-acetyl-D-glucosamine-diphosphorylundecaprenol + 2 H+ = UDP + ManNAcA-GlcNAc-diphosphorylundecaprenol + H2O

488808

-

2.4.1.180

2 entries

2.4.1.187

UDP-N-acetylmannosamine + N-acetylglucosaminyl diphosphoryl-undecaprenol = UDP + N-acetyl-beta-D-mannosaminyl-1,4-N-acetyl-D-glucosaminyldiphosphoundecaprenol

488820, 704295

-

2.4.1.188

UDP-glucose + N-acetyl-D-glucosaminyldiphosphoundecaprenol = UDP + beta-D-glucosyl-1,4-N-acetyl-D-glucosaminyldiphosphoundecaprenol

488821

-

2.4.1.303

UDP-alpha-D-galactose + N-acetyl-alpha-D-glucosaminyl-diphospho-ditrans,octacis-undecaprenol = UDP + beta-D-Gal-beta-(1->3)-alpha-D-GlcNAc-diphospho-ditrans,octacis-undecaprenol

722373

-

2.4.1.304

UDP-alpha-D-galactose + N-acetyl-alpha-D-glucosaminyl-diphospho-ditrans,octacis-undecaprenol = UDP + beta-D-Gal-(1->4)-alpha-D-GlcNAc-diphospho-ditrans,octacis-undecaprenol

722531

-

2.4.1.305

UDP-alpha-D-glucose + N-acetyl-alpha-D-glucosaminyl-diphospho-ditrans,octacis-undecaprenol = UDP + beta-D-Glc-(1->3)-alpha-D-GlcNAc-diphospho-ditrans,octacis-undecaprenol

722520

-

2.4.1.343

UDP-alpha-D-galactose + N-acetyl-alpha-D-glucosaminyl-diphospho-ditrans,octacis-undecaprenol = UDP + alpha-D-Gal-(1->3)-alpha-D-GlcNAc-diphospho-ditrans,octacis-undecaprenol

740263

-

2.4.1.348

GDP-alpha-D-mannose + N-acetyl-alpha-D-glucosaminyl-diphospho-ditrans,octacis-undecaprenol = GDP + alpha-D-mannosyl-(1->3)-N-acetyl-alpha-D-glucosaminyl-diphospho-ditrans,octacis-undecaprenol

745286, 745287, 745794

-

5.1.3.26

N-acetyl-alpha-D-glucosaminyl-diphospho-ditrans,octacis-undecaprenol = N-acetyl-alpha-D-galactosaminyl-diphospho-ditrans,octacis-undecaprenol

722673

-

Product in Enzyme-catalyzed Reactions (3 results)

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Show Product (3 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

2.7.8.13

UDP-N-acetyl-alpha-D-glucosamine + ditrans,octacis-undecaprenyl phosphate = UMP + N-acetyl-alpha-D-glucosaminyl-diphospho-ditrans,octacis-undecaprenol

-

-

2.7.8.33

UDP-N-acetyl-alpha-D-glucosamine + ditrans,octacis-undecaprenyl phosphate = UMP + N-acetyl-alpha-D-glucosaminyl-diphospho-ditrans,octacis-undecaprenol

-

-

2.7.8.33

UDP-N-acetyl-D-glucosamine + ditrans,polycis-undecaprenyl phosphate = UMP + N-acetyl-D-glucosaminyldiphospho-ditrans,polycis-undecaprenol

-

-

2.7.8.33

2 entries

Enzyme Kinetic Parameters

K_M Value (1 result)

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Show KM Value (1 entry)

EC NUMBER

KM VALUE [MM]

KM VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

2.4.1.305

-999

-

it is not possible to determine the accurate Km and Vmax values for the standard acceptor substrate N-acetyl-D-glucosaminyl-alpha-diphospho-11-phenoxyundecaprenol due to its hydrophobic character

722520

References & Links

Literature References (13)

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Show Reference (13 entries)

BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

488808

3275612

Characterization of an Escherichia coli rff mutant defective in transfer of N-acetylmannosaminuronic acid (ManNAcA) from UDP-ManNAcA to a lipid-linked intermediate involved in enterobacterial common antigen synthesis

1988

Barr, K.; Ward, S.; Meier-Dieter, U.; Mayer, H.; Rick, P.D.

J. Bacteriol.

170

228-233

488820

2977387

Partial purification and properties of UDP-N-acetylmannosamine:N-acetylglucosaminyl pyrophosphorylundecaprenol N-acetylmannosaminyltransferase from Bacillus subtilis

1988

Murazumi, N.; Kumita, K.; Araki, Y.; Ito, E.

J. Biochem.

104

980-984

488821

2977388

Solubilization and properties of UDP-D-glucose:N-acetylglucosaminyl pyrophosphorylundecaprenol glucosyltransferase from Bacillus coagulans AHU 1366 membranes

1988

Kumita, K.; Murazumi, N.; Araki, Y.; Ito, E.

J. Biochem.

104

985-988

704295

19376878

The N-acetylmannosamine transferase catalyzes the first committed step of teichoic acid assembly in Bacillus subtilis and Staphylococcus aureus

2009

D‘Elia, M.A.; Henderson, J.A.; Beveridge, T.J.; Heinrichs, D.E.; Brown, E.D.

J. Bacteriol.

191

4030-4034

721557

21188072

The cell wall teichuronic acid synthetase (TUAS) is an enzyme complex located in the cytoplasmic membrane of Micrococcus luteus

2010

Deng, L.L.; Alexander, A.A.; Lei, S.; Anderson, J.S.

Biochem. Res. Int.

2010

395758

722373

18536883

Acceptor substrate specificity of UDP-Gal:GlcNAc-R beta1,3-galactosyltransferase (WbbD) from Escherichia coli O7:K1

2008

Brockhausen, I.; Riley, J.G.; Joynt, M.; Yang, X.; Szarek, W.A.

Glycoconj. J.

25

663-673

722520

18487334

Characterization of two beta-1,3-glucosyltransferases from Escherichia coli serotypes O56 and O152

2008

Brockhausen, I.; Hu, B.; Liu, B.; Lau, K.; Szarek, W.A.; Wang, L.; Feng, L.

J. Bacteriol.

190

4922-4932

722531

21057010

Wang, L.; Brockhausen, I.: Biochemical characterization of UDP-Gal:GlcNAc-pyrophosphate-lipid beta-1,4-Galactosyltransferase WfeD, a new enzyme from Shigella boydii type 14 that catalyzes the second step in O-antigen repeating-unit synthesis

2010

Xu, C.; Liu, B.; Hu, B.; Han, Y.; Feng, L.; Allingham, J.S.; Szarek, W.A.

J. Bacteriol.

193

449-459

722673

19923219

A novel epimerase that converts GlcNAc-P-P-undecaprenol to GalNAc-P-P-undecaprenol in Escherichia coli O157

2009

Rush, J.S.; Alaimo, C.; Robbiani, R.; Wacker, M.; Waechter, C.J.

J. Biol. Chem.

285

1671-1680

740263

27196310

Biochemical characterization of the novel alpha-1, 3-galactosyltransferase WclR from Escherichia coli O3

2016

Chen, C.; Liu, B.; Xu, Y.; Utkina, N.; Zhou, D.; Danilov, L.; Torgov, V.; Veselovsky, V.; Feng, L.

Carbohydr. Res.

430

36-43

745286

22875852

Biosynthesis of the polymannose lipopolysaccharide O-antigens from Escherichia coli serotypes O8 and O9a requires a unique combination of single- and multiple-active site mannosyltransferases

2012

Greenfield, L.; Richards, M.; Li, J.; Wakarchuk, W.; Lowary, T.; Whitfield, C.

J. Biol. Chem.

287

35078-35091

745287

22989876

Domain organization of the polymerizing mannosyltransferases involved in synthesis of the Escherichia coli O8 and O9a lipopolysaccharide O-antigens

2012

Greenfield, L.; Richards, M.; Vinogradov, E.; Wakarchuk, W.; Lowary, T.; Whitfield, C.

J. Biol. Chem.

287

38135-38149

745794

9570406

Synthesis of Escherichia coli O9a polysaccharide requires the participation of two domains of WbdA, a mannosyltransferase encoded within the wb gene cluster

1998

Kido, N.; Sugiyama, T.; Yokochi, T.; Kobayashi, H.; Okawa, Y.

Mol. Microbiol.

27

1213-1221

Links to other databases for N-acetyl-alpha-D-glucosaminyl-diphospho-ditrans,octacis-undecaprenol

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Show Links (1 entry)