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Ligand ditrans,polycis-undecaprenyl phosphate

Basic Ligand Information

Molecular Structure

Pathway Source

Pathways

BRENDA

peptidoglycan biosynthesis, teichoic acid biosynthesis

KEGG

Peptidoglycan biosynthesis, Teichoic acid biosynthesis

MetaCyc

2-acetamido-4-amino-2,4,6-trideoxy-alpha-D-galactosyl-diphospho-ditrans,octacis-undecaprenol biosynthesis, acetan biosynthesis, Brucella abortus O antigen biosynthesis, colanic acid (Escherichia coli K12) biosynthesis, di-trans,poly-cis-undecaprenyl phosphate biosynthesis, 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, peptidoglycan biosynthesis I (meso-diaminopimelate containing), peptidoglycan biosynthesis II (staphylococci), peptidoglycan biosynthesis IV (Enterococcus faecium), peptidoglycan biosynthesis V (beta-lactam resistance), 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), polymyxin resistance, Porphyromonas gingivalis O-LPS antigen biosynthesis, Salmonella enterica serotype O:13 O antigen biosynthesis, Salmonella enterica serotype O:18 O antigen biosynthesis, Salmonella enterica serotype O:2 O antigen biosynthesis, Salmonella enterica serotype O:3,10 O antigen biosynthesis, Salmonella enterica serotype O:39 O antigen biosynthesis, Salmonella enterica serotype O:4 O antigen biosynthesis (group B1), Salmonella enterica serotype O:54 O antigen biosynthesis, Salmonella enterica serotype O:6,7 O antigen biosynthesis, Salmonella enterica serotype O:8 O antigen biosynthesis, Salmonella enterica serotype O:9 O antigen biosynthesis, Salmonella enterica serotype O:9,46 O antigen biosynthesis, Salmonella enterica serotype O:9,46,27 O antigen biosynthesis, Shigella boydii serotype 6 O antigen biosynthesis, succinoglycan biosynthesis, teichuronic acid biosynthesis (B. subtilis 168), type I lipoteichoic acid biosynthesis (S. aureus), xanthan biosynthesis more

Show all BRENDA pathways known for ditrans,polycis-undecaprenyl phosphate

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Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (13 results)

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Show Natural Substrate (13 entries)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

2.4.1.54

GDPmannose + undecaprenyl phosphate = GDP + D-mannosyl-1-phosphoundecaprenol

489291

-

2.4.1.78

UDP-glucose + ficaprenol phosphate = UDP + ficaprenolphosphate-glucose

489379

-

2.7.8.13

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

738596

-

2.7.8.13

UDP-Mur2Ac(oyl-L-Ala-D-gamma-Glu-L-Lys-D-Ala-D-Ala) + undecaprenyl phosphate = UMP + Mur2Ac(oyl-L-Ala-D-gamma-Glu-L-Lys-D-Ala-D-Ala)-diphosphoundecaprenol

660721, 662239, 662009

-

2.7.8.13

UDP-Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala) + undecaprenyl phosphate = UMP + Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphosphoundecaprenol

704218, 704219, 737788

-

2.7.8.13

UDP-MurNAc-pentapeptide + undecaprenyl phosphate = UMP + MurNAc-pentapeptide-diphosphoundecaprenol

692509

-

2.7.8.13

UDPMur2Ac(oyl-L-Ala-D-gamma-Glu-L-Lys-D-Ala-D-Ala) + undecaprenyl phosphate = UMP + Mur2Ac(oyl-L-Ala-D-gamma-Glu-L-Lys-D-Ala-D-Ala)-diphosphoundecaprenol

662239

-

2.7.8.13

UDP-MurNAc-pentapeptide + undecaprenyl-phosphate = UMP + MurNAc-pentapeptide diphosphoryl undecaprenol

645343, 645340

-

2.7.8.13

6 entries

2.7.8.31

UDP-glucose + ditrans,octacis-undecaprenyl phosphate = UMP + alpha-D-glucopyranosyl-diphospho-ditrans,octacis-undecaprenol

702828, 704249, 704251, 704257

-

2.7.8.33

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

738596, 737788

-

2.7.8.33

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

708918, 708920, 707104

-

2.7.8.33

2 entries

2.7.8.40

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

722529, 739417

-

2.7.8.B2

UDP-4-deoxy-4-formamido-beta-L-arabinopyranose + undecaprenyl phosphate = UDP + 4-deoxy-4-formamido-beta-L-arabinopyranosyl undecaprenyl phosphate

698730

-

In Vivo Product in Enzyme-catalyzed Reactions (8 results)

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Show Natural Product (8 entries)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

2.4.2.43

4-amino-4-deoxy-alpha-L-arabinopyranosyl di-trans,poly-cis-undecaprenyl phosphate + lipid IVA = lipid IIA + di-trans,poly-cis-undecaprenyl phosphate

0

-

2.4.2.43

4-amino-4-deoxy-alpha-L-arabinopyranosyl ditrans,octacis-undecaprenyl phosphate + alpha-Kdo-(2->4)-alpha-Kdo-(2->6)-lipid A = alpha-Kdo-(2->4)-alpha-Kdo-(2->6)-[4-P-L-Ara4N]-lipid A + ditrans,octacis-undecaprenyl phosphate

0

-

2.4.2.43

4-amino-4-deoxy-alpha-L-arabinopyranosyl ditrans,octacis-undecaprenyl phosphate + alpha-Kdo-(2->4)-alpha-Kdo-(2->6)-lipid A = alpha-Kdo-(2->4)-Kdo-(2->6)-[4-P-L-Ara4N]-lipid A + ditrans,octacis-undecaprenyl phosphate

0

-

2.4.2.43

4-amino-4-deoxy-alpha-L-arabinopyranosyl undecaprenyl phosphate + lipid IV(A) = lipid II(A) + undecaprenyl phosphate

0

-

2.4.2.43

4 entries

2.4.2.B4

3-deoxy-alpha-D-manno-oct-2-ulopyranosyl-(2->4)-3-deoxy-alpha-D-manno-oct-2-ulopyranosyl-(2->6)-2-deoxy-2-[[(3R)-3-hydroxypentadecanoyl]amino]-3-O-[(3R)-3-hydroxytetradecanoyl]-4-O-phosphono-beta-D-glucopyranosyl-(1->6)-2-deoxy-3-O-[(3R)-3-hydroxytetradecanoyl]-2-[[(3R)-3-hydroxytetradecanoyl]amino]-1-O-phosphono-alpha-D-glucopyranose + 4-amino-4-deoxy-alpha-L-arabinopyranosyl undecaprenyl phosphate = 3-deoxy-alpha-D-manno-oct-2-ulopyranosyl-(2->4)-3-deoxy-alpha-D-manno-oct-2-ulopyranosyl-(2->6)-2-deoxy-2-[[(3R)-3-hydroxypentadecanoyl]amino]-3-O-[(3R)-3-hydroxytetradecanoyl]-4-O-(4-amino-4-deoxy-alpha-L-arabinopyranosyl)phosphono-beta-D-glucopyranosyl-(1->6)-2-deoxy-3-O-[(3R)-3-hydroxytetradecanoyl]-2-[[(3R)-3-hydroxytetradecanoyl]amino]-1-O-(4-amino-4-deoxy-alpha-L-arabinopyranosyl)phosphono-alpha-D-glucopyranose + undecaprenyl phosphate

0

-

2.7.1.66

ATP + undecaprenol = ADP + undecaprenyl phosphate

0

-

3.6.1.27

ditrans,octacis-undecaprenyl diphosphate + H2O = ditrans,octacis-undecaprenyl phosphate + phosphate

0

-

3.6.1.27

undecaprenyl diphosphate + H2O = undecaprenyl phosphate + phosphate

0, 210606, 210607

-

3.6.1.27

2 entries

Substrate in Enzyme-catalyzed Reactions (49 results)

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Show Substrate (49 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

2.4.1.117

UDP-glucose + ficaprenyl phosphate = UDP + ficaprenyl beta-D-glucosyl phosphate

488480

-

2.4.1.54

GDPmannose + ficaprenyl phosphate = GDP + mannosyl-1-phosphorylficaprenol

489288, 489290

-

2.4.1.54

UDPglucose + ficaprenyl phosphate = GDP + glucosyl-1-phosphorylficaprenol

489290

-

2.4.1.54

GDPmannose + undecaprenyl phosphate = GDP + D-mannosyl-1-phosphoundecaprenol

489291, 489288, 489290

-

2.4.1.54

3 entries

2.4.1.78

UDP-glucose + ficaprenol phosphate = UDP + ficaprenolphosphate-glucose

489379

-

2.4.1.83

GDP-mannose + C55-undecaprenyl phosphate = GDP + C55-undecaprenyl D-mannosyl phosphate

692257

-

2.4.2.53

UDP-4-deoxy-4-formamido-beta-L-arabinopyranose + ditrans,polycis-undecaprenyl phosphate = UDP + 4-deoxy-4-formamido-alpha-L-arabinopyranosyl ditrans,polycis-undecaprenyl phosphate

698730

-

2.7.8.13

UDP-MurNAc-pentapeptide + C55-isoprenyl phosphate = C55-isoprenyl-diphosphate-MurNAc-pentapeptide

645334, 645331

-

2.7.8.13

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

738596

-

2.7.8.13

UDP-MurNAc-pentapeptide + undecaprenoid-1-ol-phosphate = lipid-P-P-MurNAc-pentapeptide + UMP

645332, 645340, 645343, 645333

-

2.7.8.13

dansyl-UDP-NAc-muramoyl-pentapeptide + undecaprenyl phosphate = UMP + dansyl-UDP-NAc-muramoyl-pentapeptide-diphosphoundecaprenol

645340

-

2.7.8.13

N-dansyl-UDP-NAc-muramoyl-L-Ala-gamma-D-Glu-meso-diaminopimelic acid-D-Ala-D-Ala + undecaprenyl phosphate = UMP + ?

675899

-

2.7.8.13

N-fluorescamine-UDP-NAc-muramoyl-L-Ala-gamma-D-Glu-meso-diaminopimelic acid-D-Ala-D-Ala + undecaprenyl phosphate = UMP + ?

675899

-

2.7.8.13

N-o-phthalaldehyde-UDP-NAc-muramoyl-L-Ala-gamma-D-Glu-meso-diaminopimelic acid-D-Ala-D-Ala + undecaprenyl phosphate = UMP + ?

675899

-

2.7.8.13

UDP-Mur2Ac(oyl-L-Ala-D-gamma-Glu-L-Lys-D-Ala-D-Ala) + undecaprenyl phosphate = UMP + Mur2Ac(oyl-L-Ala-D-gamma-Glu-L-Lys-D-Ala-D-Ala)-diphosphoundecaprenol

662239, 660721, 662009

-

2.7.8.13

UDP-Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala) + undecaprenyl phosphate = UMP + Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphosphoundecaprenol

704218, 704219, 737580, 737788

-

2.7.8.13

UDP-MurNAc + undecaprenyl phosphate = UMP + MurNAc-diphosphoundecaprenol

737788

-

2.7.8.13

UDP-MurNAc-(oyl-L-Ala) + undecaprenyl phosphate = UMP + MurNAc(oyl-L-Ala)-diphosphoundecaprenol

737788

-

2.7.8.13

UDP-MurNAc-(oyl-L-Ala-gamma-D-Glu) + undecaprenyl phosphate = UMP + MurNAc(oyl-L-Ala-gamma-D-Glu)-diphosphoundecaprenol

737788

-

2.7.8.13

UDP-MurNAc-(oyl-L-Ala-gamma-D-Glu-meso-diaminopimelate) + undecaprenyl phosphate = UMP + MurNAc(oyl-L-Ala-gamma-D-Glu-meso-diaminopimelate)-diphosphoundecaprenol

737788

-

2.7.8.13

UDP-MurNAc-Ala-D-Glu-Lys + undecaprenyl phosphate = UMP + MurNAc-Ala-D-Glu-Lys-diphosphoundecaprenol

645333

-

2.7.8.13

UDP-MurNAc-Ala-D-Glu-Lys-D-Ala + undecaprenyl phosphate = UMP + MurNAc-Ala-D-Glu-Lys-D-Ala-diphosphoundecaprenol

645333

-

2.7.8.13

UDP-MurNAc-Ala-D-Glu-Lys-D-Ala-Gly + undecaprenyl phosphate = UMP + MurNAc-Ala-D-Glu-Lys-D-Ala-Gly-diphosphoundecaprenol

645333

-

2.7.8.13

UDP-MurNAc-Ala-D-Glu-Lys-Gly-D-Ala + undecaprenyl phosphate = UMP + MurNAc-Ala-D-Glu-Lys-Gly-D-Ala-diphosphoundecaprenol

645333

-

2.7.8.13

UDP-MurNAc-Ala-D-Glu-Orn-D-Ala-D-Ala + undecaprenyl phosphate = UMP + MurNAc-Ala-D-Glu-Orn-D-Ala-D-Ala-diphosphoundecaprenol

645333

-

2.7.8.13

UDP-MurNAc-Ala-Glu-Lys + undecaprenyl phosphate = UMP + MurNAc-Ala-Glu-Lys-diphosphoundecaprenol

645333

-

2.7.8.13

UDP-MurNAc-Gly-D-Glu-Lys-D-Ala-D-Ala + undecaprenyl phosphate = UMP + MurNAc-Gly-D-Glu-Lys-D-Ala-D-Ala-diphosphoundecaprenol

645333

-

2.7.8.13

UDP-MurNAc-L-Ala-gamma-D-Glu-m-DAP-[Nepsilon-dansyl]-D-Ala-D-Ala + undecaprenyl phosphate = UMP + MurNAc-L-Ala-gamma-D-Glu-m-DAP-[Nepsilon-dansyl]-D-Ala-D-Ala-diphosphoundecaprenol

704218

-

2.7.8.13

UDP-MurNAc-pentapeptide + undecaprenyl phosphate = UMP + MurNAc-pentapeptide-diphosphoundecaprenol

692509

-

2.7.8.13

UDP-MurNAc-pentapeptide + undecaprenyl phosphate = UMP + undecaprenol diphosphate N-acetylmuramyl pentapeptide

694514

-

2.7.8.13

UDP-N-acetylmuramoyl-pentapeptide + undecaprenyl phosphate = ?

725566

-

2.7.8.13

UDP-N-acetylmuramoyl-pentapeptide + undecaprenyl phosphate = UMP + N-acetylmuramoyl-pentapeptide-diphosphoundecaprenol

690996

-

2.7.8.13

UDP-NAc-muramoyl-L-Ala-gamma-D-Glu-meso-diaminopimelic acid-D-Ala-D-Ala + undecaprenyl phosphate = UMP + ?

675899

-

2.7.8.13

UDP-NAc-muramoyl-pentapeptide + undecaprenyl phosphate = UMP + undecaprenyl-phospho-NAc-muramoyl-pentapeptide

676084

-

2.7.8.13

UDPMur2Ac(oyl-L-Ala-D-gamma-Glu-L-Lys-D-Ala-D-Ala) + undecaprenyl phosphate = UMP + Mur2Ac(oyl-L-Ala-D-gamma-Glu-L-Lys-D-Ala-D-Ala)-diphosphoundecaprenol

662239

-

2.7.8.13

UDP-MurNAc-pentapeptide + undecaprenyl-phosphate = UMP + MurNAc-pentapeptide diphosphoryl undecaprenol

645343, 645340

-

2.7.8.31

UDP-glucose + ditrans,octacis-undecaprenyl phosphate = UMP + alpha-D-glucopyranosyl-diphospho-ditrans,octacis-undecaprenol

702828, 704249, 704251, 704257

-

2.7.8.31

UDP-alpha-D-galactose + undecaprenyl phosphate = UMP + alpha-D-galactosyl-diphosphoundecaprenol

722541

-

2.7.8.31

UDP-alpha-D-glucose + undecaprenyl phosphate = UMP + alpha-D-glucosyl-diphosphoundecaprenol

722541

-

2.7.8.33

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

738596, 737788

-

2.7.8.33

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

723725, 708918, 708920, 707104, 708621

-

2.7.8.36

UDP-6-hydroxybacillosamine + undecaprenyl phosphate = 6-hydroxybacillosaminyl-diphosphoundecaprenol + UMP

721604

-

2.7.8.36

UDP-bacillosamine + undecaprenyl phosphate = bacillosaminyl-diphosphoundecaprenol + UMP

721604

-

2.7.8.36

UDP-N,N'-diacetylbacillosamine + undecaprenyl phosphate = UMP + N,N'-diacetylbacillosaminyl-diphospho-undecaprenol

718901

-

2.7.8.13

29 entries

2.7.8.31

3 entries

2.7.8.33

2 entries

2.7.8.36

3 entries

2.7.8.40

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

722529, 739417

-

2.7.8.6

UDP-alpha-D-galactose + undecaprenyl phosphate = UMP + alpha-D-galactosyl-diphosphoundecaprenol

722529, 722344, 722358

-

2.7.8.6

UDP-D-N-acetylhexosamine + undecaprenyl phosphate = UMP + N-acetyl hexosaminyl-diphosphoundecaprenol

722529

-

2.7.8.6

UDP-N-acetyl-D-galactosamine + undecaprenyl phosphate = UMP + N-acetyl-D-galactosaminyl-diphosphoundecaprenol

722529

-

2.7.8.6

3 entries

2.7.8.B2

UDP-4-deoxy-4-formamido-beta-L-arabinopyranose + undecaprenyl phosphate = UDP + 4-deoxy-4-formamido-beta-L-arabinopyranosyl undecaprenyl phosphate

698730

-

Product in Enzyme-catalyzed Reactions (15 results)

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Show Product (15 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

2.4.2.43

4-amino-4-deoxy-alpha-L-arabinopyranosyl di-trans,poly-cis-undecaprenyl phosphate + lipid IVA = lipid IIA + di-trans,poly-cis-undecaprenyl phosphate

0

-

2.4.2.43

4-amino-4-deoxy-alpha-L-arabinopyranosyl ditrans,octacis-undecaprenyl phosphate + alpha-Kdo-(2->4)-alpha-Kdo-(2->6)-lipid A = alpha-Kdo-(2->4)-alpha-Kdo-(2->6)-[4-P-L-Ara4N]-lipid A + ditrans,octacis-undecaprenyl phosphate

0

-

2.4.2.43

4-amino-4-deoxy-alpha-L-arabinopyranosyl ditrans,octacis-undecaprenyl phosphate + alpha-Kdo-(2->4)-alpha-Kdo-(2->6)-lipid A = alpha-Kdo-(2->4)-Kdo-(2->6)-[4-P-L-Ara4N]-lipid A + ditrans,octacis-undecaprenyl phosphate

0

-

2.4.2.43

4-amino-4-deoxy-alpha-L-arabinopyranosyl undecaprenyl phosphate + lipid IV(A) = lipid II(A) + undecaprenyl phosphate

0

-

2.4.2.43

4 entries

2.4.2.B4

3-deoxy-alpha-D-manno-oct-2-ulopyranosyl-(2->4)-3-deoxy-alpha-D-manno-oct-2-ulopyranosyl-(2->6)-2-deoxy-2-[[(3R)-3-hydroxypentadecanoyl]amino]-3-O-[(3R)-3-hydroxytetradecanoyl]-4-O-phosphono-beta-D-glucopyranosyl-(1->6)-2-deoxy-3-O-[(3R)-3-hydroxytetradecanoyl]-2-[[(3R)-3-hydroxytetradecanoyl]amino]-1-O-phosphono-alpha-D-glucopyranose + 4-amino-4-deoxy-alpha-L-arabinopyranosyl undecaprenyl phosphate = 3-deoxy-alpha-D-manno-oct-2-ulopyranosyl-(2->4)-3-deoxy-alpha-D-manno-oct-2-ulopyranosyl-(2->6)-2-deoxy-2-[[(3R)-3-hydroxypentadecanoyl]amino]-3-O-[(3R)-3-hydroxytetradecanoyl]-4-O-(4-amino-4-deoxy-alpha-L-arabinopyranosyl)phosphono-beta-D-glucopyranosyl-(1->6)-2-deoxy-3-O-[(3R)-3-hydroxytetradecanoyl]-2-[[(3R)-3-hydroxytetradecanoyl]amino]-1-O-(4-amino-4-deoxy-alpha-L-arabinopyranosyl)phosphono-alpha-D-glucopyranose + undecaprenyl phosphate

0

-

2.7.1.108

CTP + ficaprenol = CDP + ficaprenyl phosphate

0

-

2.7.1.66

ATP + C55-isoprenoid alcohol = ADP + C55-isoprenoid alcohol monophosphate

0

-

2.7.1.66

ATP + ficaprenol = ADP + ficaprenyl phosphate

0, 641761

-

2.7.1.66

ATP + undecaprenol = ADP + undecaprenyl monophosphate

641759, 0

-

2.7.1.66

ATP + undecaprenol = ADP + undecaprenyl phosphate

0

-

2.7.4.29

ditrans-octacis-undecaprenyl diphosphate + alpha-D-Kdo-(2->4)-alpha-D-Kdo-(2->6)-lipid A = ditrans-octacis-undecaprenyl phosphate + alpha-D-Kdo-(2->4)-alpha-D-Kdo-(2->6)-lipid A 1-diphosphate

0

-

2.7.4.29

ditrans-octacis-undecaprenyl diphosphate + alpha-D-Kdo-(2->4)-alpha-D-Kdo-(2->6)-lipid A = ditrans-octacis-undecaprenyl phosphate + alpha-D-Kdo-(2->4)-alpha-D-Kdo-(2->6)-lipid A 4'-diphosphate

0

-

2.7.1.66

4 entries

2.7.4.29

2 entries

3.1.3.27

undecaprenyldiphosphate + H2O = undecaprenylphosphate + phosphate

0

-

3.6.1.27

ditrans,octacis-undecaprenyl diphosphate + H2O = ditrans,octacis-undecaprenyl phosphate + phosphate

0

-

3.6.1.27

undecaprenyl diphosphate + H2O = undecaprenyl phosphate + phosphate

0, 210606, 210607

-

3.6.1.27

2 entries

Activator in Enzyme-catalyzed Reactions (1 result)

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Show Activating Compound (1 entry)

EC NUMBER

COMMENTARY

LITERATURE

ENZYME 3D STRUCTURE

2.7.8.13

stimulates exchange reaction

645332

-

Inhibitor in Enzyme-catalyzed Reactions (1 result)

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Show Inhibitors (1 entry)

EC NUMBER

COMMENTARY

LITERATURE

ENZYME 3D STRUCTURE

2.4.1.54

inhibits in excess amount

489288

-

Enzyme Kinetic Parameters

k_cat Value (Turnover Number) (18 results)

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Show Turnover Number (18 entries)

EC NUMBER

TURNOVER NUMBER [1/S]

TURNOVER NUMBER MAXIMUM [1/S]

COMMENTARY

LITERATURE

2.7.8.13

-999

-

11fold increase in kcat for mutant D98N at pH 9.4 (ca. 0.0083 1/sec) compared to pH 7.2

690996

2.7.8.13

0.00005

-

mutant H289R

690996

2.7.8.13

0.00083

-

mutant D99N

690996

2.7.8.13

0.00117

-

mutant D98N

690996

2.7.8.13

0.0015

-

mutant K116Q

690996

2.7.8.13

0.00383

-

mutant H290R

690996

2.7.8.13

0.0123

-

mutant D174N

690996

2.7.8.13

0.0135

-

mutant N171A

690996

2.7.8.13

0.0163

-

mutant D231N

690996

2.7.8.13

0.023

-

mutant H45R

690996

2.7.8.13

0.027

-

mutant K48Q

690996

2.7.8.13

0.0317

-

mutant H291R

690996

2.7.8.13

0.065

-

mutant D177N

690996

2.7.8.13

0.0717

-

mutant N168A

690996

2.7.8.13

0.53

-

mutant E299Q

690996

2.7.8.13

5.3

-

wild-type

690996

2.7.8.13

5.33

-

-

662239

2.7.8.13

17 entries

2.7.8.33

1.2

-

pH 8, 65°C

708920

K_M Value (21 results)

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Show KM Value (21 entries)

EC NUMBER

KM VALUE [MM]

KM VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

2.4.1.54

0.02

0.04

-

489290

2.4.1.83

0.00117

-

-

692257

2.7.8.13

-999

-

3fold increase in KM for mutant D98N at pH 9.4 (ca. 1.2 mM) compared to pH 7.2

690996

2.7.8.13

0.15

-

mutant H290R

690996

2.7.8.13

0.16

-

-

662239

2.7.8.13

0.16

-

wild-type

690996

2.7.8.13

0.17

-

mutant D174N

690996

2.7.8.13

0.17

-

mutant D231N

690996

2.7.8.13

0.21

-

mutant N168A

690996

2.7.8.13

0.22

-

mutant E299Q

690996

2.7.8.13

0.22

-

mutant H45R

690996

2.7.8.13

0.22

-

mutant K116Q

690996

2.7.8.13

0.23

-

mutant D177N

690996

2.7.8.13

0.24

-

mutant N171A

690996

2.7.8.13

0.25

-

mutant H289R

690996

2.7.8.13

0.26

-

mutant K48Q

690996

2.7.8.13

0.27

-

mutant H291R

690996

2.7.8.13

0.32

-

mutant D98N

690996

2.7.8.13

0.35

-

mutant D99N

690996

2.7.8.13

17 entries

2.7.8.33

0.12

-

pH 8, 65°C

708920

2.7.8.6

0.0785

-

in 50 mM Tris-HCl (pH 8.5), 25 mM MgCl2, 1% (w/v) CHAPS, at 37°C

722358

References & Links

Literature References (47)

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Show Reference (47 entries)

BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

210606

4332017

Mechanism of action of bacitracin: complexation with metal ion and C 55 -isoprenyl pyrophosphate

1971

Stone, K.J.; Strominger, J.L.

Proc. Natl. Acad. Sci. USA

68

3223-3227

210607

4341539

Purification and properties of C 55 -isoprenylpyrophosphate phosphatase from Micrococcus lysodeikticus

1972

Goldman, R.; Strominger, J.L.

J. Biol. Chem.

247

5116-5122

488480

438216

Properties of a soluble polyprenyl phosphate: UDP-D-glucose glucosyltransferase

1979

Villemez, C.L.; Carlo, P.L.

J. Biol. Chem.

254

4814-4819

489288

5350943

Studies on the biosynthesis of mannan in Micrococcus lysodeikticus. II. The enzymatic synthesis of mannosyl-l-phosphoryl-undecaprenol

1969

Lahav, M.; Chiu, T.H.; Lennarz, W.J.

J. Biol. Chem.

244

5890-5898

489290

4697395

Biosynthesis of mannosyl- and glucosyl-phosphoryl-polyprenols in cotton fibers

1973

Forsee, W.T.; Elbein, A.D.

J. Biol. Chem.

248

2858-2867

489291

8514752

Mannosylphosphoryldolichol-mediated reactions in oligosaccharide-P-P-dolichol biosynthesis. Recognition of the saturated alpha-isoprene unit of the mannosyl donor by pig brain mannosyltransferases

1993

Rush, J.S.; Shelling, J.G.; Zingg, N.S.; Ray, P.H.; Waechter, C.J.

J. Biol. Chem.

268

13110-13117

489379

4373050

Formation of polyprenol monophosphate glucose in Shigella flexneri

1974

Jankowski, W.; Mankowski, T.; Chojnacki, T.

Biochim. Biophys. Acta

337

153-162

641759

224936

Characterization of undecaprenol kinase from Lactobacillus plantarum

1979

Kalin, J.R.; Allen, C.M.

Biochim. Biophys. Acta

574

112-122

641761

4373523

Isoprenoid alcohol kinase--a third butanol-soluble enzyme in Klebsiella aerogenes membranes

1974

Poxton, I.R.; Lomax, J.A.; Sutherland, I.W.

J. Gen. Microbiol.

84

231-233

645331

4340168

Complex lipid requirements for detergent-solubilized phosphoacetylmuramyl-pentapeptide translocase from Micrococcus luteus

1972

Umbreit, J.N.; Strominger, J.L.

Proc. Natl. Acad. Sci. USA

69

1972-1974

645332

4694725

Initial membrane reaction in peptidoglycan synthesis. Lipid dependence of phospho-n-acetylmuramyl-pentapeptide translocase (exchange reaction)

1973

Pless, D.D.; Neuhaus, F.C.

J. Biol. Chem.

248

1568-1576

645333

4208473

On the specificity of phospho-N-acetylmuramyl-pentapeptide translocase. The peptide subunit of uridine diphosphate-N-actylmuramyl-pentapeptide

1974

Hammes, W.P.; Neuhaus, F.C.

J. Biol. Chem.

249

3140-3150

645334

215212

Phospho-N-acetylmuramoyl-pentapeptide-transferase of Escherichia coli K12. Properties of the membrane-bound and the extracted and partially purified enzyme

1978

Geis, A.; Plapp, R.

Biochim. Biophys. Acta

527

414-424

645340

8631795

Slow binding inhibition of phospho-N-acetylmuramyl-pentapeptide-translocase (Escherichia coli) by mureidomycin A

1996

Brandish, P.E.; Burnham, M.K.; Lonsdale, J.T.; Southgate, R.; Inukai, M.; Bugg, T.D.H.

J. Biol. Chem.

271

7609-7614

645343

12654311

Targeting the MraY and MurG bacterial enzymes for antimicrobial therapeutic intervention

2003

Zawadzke, L.E.; Wu, P.; Cook, L.; Fan, L.; Casperson, M.; Kishnani, M.; Calambur, D.; Hofstead, S.J.; Padmanabha, R.

Anal. Biochem.

314

243-252

660721

14982781

Fluorescence detection-based functional assay for high-throughput screening for MraY

2004

Stachyra, T.; Dini, C.; Ferrari, P.; Bouhss, A.; Van Heijenoort, J.; Mengin-Lecreulx, D.; Blanot, D.; Biton, J.; Le Beller, D.

Antimicrob. Agents Chemother.

48

897-902

662009

14996806

Phospho-N-acetyl-muramyl-pentapeptide translocase from Escherichia coli: catalytic role of conserved aspartic acid residues

2004

Lloyd, A.J.; Brandish, P.E.; Gilbey, A.M.; Bugg, T.D.H.

J. Bacteriol.

186

1747-1757

662239

15131133

Purification and characterization of the bacterial MraY translocase catalyzing the first membrane step of peptidoglycan biosynthesis

2004

Bouhss, A.; Crouvoisier, M.; Blanot, D.; Mengin-Lecreulx, D.

J. Biol. Chem.

279

29974-29980

675899

17216029

Fluorescent reagents for in vitro studies of lipid-linked steps of bacterial peptidoglycan biosynthesis: derivatives of UDPMurNAc-pentapeptide containing d-cysteine at position 4 or 5

2006

Schouten, J.A.; Bagga, S.; Lloyd, A.J.; de Pascale, G.; Dowson, C.G.; Roper, D.I.; Bugg, T.D.

Mol. Biosyst.

2

484-491

676084

17640276

The essential peptidoglycan glycosyltransferase MurG forms a complex with proteins involved in lateral envelope growth as well as with proteins involved in cell division in Escherichia coli

2007

Mohammadi, T.; Karczmarek, A.; Crouvoisier, M.; Bouhss, A.; Mengin-Lecreulx, D.; den Blaauwen, T.

Mol. Microbiol.

65

1106-1121

690996

18672909

Active site mapping of MraY, a member of the polyprenyl-phosphate N-acetylhexosamine 1-phosphate transferase superfamily, catalyzing the first membrane step of peptidoglycan biosynthesis

2008

Al-Dabbagh, B.; Henry, X.; El Ghachi, M.; Auger, G.; Blanot, D.; Parquet, C.; Mengin-Lecreulx, D.; Bouhss, A.

Biochemistry

47

8919-8928

692257

18563288

A thermostable dolichol phosphoryl mannose synthase responsible for glycoconjugate synthesis of the hyperthermophilic archaeon Pyrococcus horikoshii

2008

Urushibata, Y.; Ebisu, S.; Matsui, I.

Extremophiles

12

665-676

692509

18791230

Genetic analysis of MraY inhibition by the {varphi}X174 protein E

2008

Zheng, Y.; Struck, D.K.; Bernhardt, T.G.; Young, R.

Genetics

180

1459-1466

694514

18075661

Synthesis of gem-difluorinated nucleoside analogues of the liposidomycins and evaluation as MraY inhibitors

2008

Xu, X.H.; Trunkfield, A.E.; Bugg, T.D.; Qing, F.L.

Org. Biomol. Chem.

6

157-161

698730

15695810

A formyltransferase required for polymyxin resistance in Escherichia coli and the modification of lipid A with 4-Amino-4-deoxy-L-arabinose. Identification and function oF UDP-4-deoxy-4-formamido-L-arabinose

2005

Breazeale, S.D.; Ribeiro, A.A.; McClerren, A.L.; Raetz, C.R.

J. Biol. Chem.

280

14154-14167

702828

18854951

Mutational analysis of the gum gene cluster required for xanthan biosynthesis in Xanthomonas oryzae pv oryzae

2008

Kim, S.Y.; Kim, J.G.; Lee, B.M.; Cho, J.Y.

Biotechnol. Lett.

31

265-270

704218

19160520

A-94964, a novel inhibitor of bacterial translocase I, produced by Streptomyces sp. SANK 60404. I. Taxonomy, isolation and biological activity

2008

Murakami, R.; Fujita, Y.; Kizuka, M.; Kagawa, T.; Muramatsu, Y.; Miyakoshi, S.; Takatsu, T.; Inukai, M.

J. Antibiot.

61

537-544

704219

19160521

A-94964, novel inhibitor of bacterial translocase I, produced by Streptomyces sp. SANK 60404. II. Physico-chemical properties and structure elucidation

2008

Fujita, Y.; Murakami, R.; Muramatsu, Y.; Miyakoshi, S.; Takatsu, T.

J. Antibiot.

61

545-549

704249

7683019

Sequential assembly and polymerization of the polyprenol-linked pentasaccharide repeating unit of the xanthan polysaccharide in Xanthomonas campestris

1993

Ielpi, L.; Couso, R.O.; Dankert, M.A.

J. Bacteriol.

175

2490-2500

704251

7928993

Mechanism of bacitracin resistance in gram-negative bacteria that synthesize exopolysaccharides

1994

Pollock, T.J.; Thorne, L.; Yamazaki, M.; Mikolajczak, M.J.; Armentrout, R.W.

J. Bacteriol.

176

6229-6237

704257

9537354

Xanthomonas campestris pv. campestris gum mutants: effects on xanthan biosynthesis and plant virulence

1998

Katzen, F.; Ferreiro, D.U.; Oddo, C.G.; Ielmini, M.V.; Becker, A.; Pühler, A.; Ielpi, L.

J. Bacteriol.

180

1607-1617

707104

19442646

Preparative enzymatic synthesis of polyprenyl-pyrophosphoryl-N-acetylglucosamine, an essential lipid intermediate for the biosynthesis of various bacterial cell envelope polymers

2009

Al-Dabbagh, B.; Blanot, D.; Mengin-Lecreulx, D.; Bouhss, A.

Anal. Biochem.

391

163-165

708621

9134438

Polyisoprenyl phosphate specificity of UDP-GlcNAc:undecaprenyl phosphate N-acetylglucosaminyl 1-P transferase from E.coli

1997

Rush, J.S.; Rick, P.D.; Waechter, C.J.

Glycobiology

7

315-322

708918

17237164

Functional characterization and membrane topology of Escherichia coli WecA, a sugar-phosphate transferase initiating the biosynthesis of enterobacterial common antigen and O-antigen lipopolysaccharide

2007

Lehrer, J.; Vigeant, K.A.; Tatar, L.D.; Valvano, M.A.

J. Bacteriol.

189

2618-2628

708920

18723618

Purification and characterization of the bacterial UDP-GlcNAc:undecaprenyl-phosphate GlcNAc-1-phosphate transferase WecA

2008

Al-Dabbagh, B.; Mengin-Lecreulx, D.; Bouhss, A.

J. Bacteriol.

190

7141-7146

718901

21542610

Biochemical characterization of the O-linked glycosylation pathway in Neisseria gonorrhoeae responsible for biosynthesis of protein glycans containing N,N-diacetylbacillosamine

2011

Hartley, M.D.; Morrison, M.J.; Aas, F.E.; B?rud, B.; Koomey, M.; Imperiali, B.

Biochemistry

50

4936-4948

721604

16618123

Direct biochemical evidence for the utilization of UDP-bacillosamine by PglC, an essential glycosyl-1-phosphate transferase in the Campylobacter jejuni N-linked glycosylation pathway

2006

Glover, K.; Weerapana, E.; Chen, M.; Imperiali, B.

Biochemistry

45

5343-5350

722344

20591829

Functional analysis of the C-terminal domain of the WbaP protein that mediates initiation of O antigen synthesis in Salmonella enterica

2010

Patel, K.; Furlong, S.; Valvano, M.

Glycobiology

20

1389-1401

722358

21856724

The C-terminal domain of the Salmonella enterica WbaP (UDP-galactose:Und-P galactose-1-phosphate transferase) is sufficient for catalytic activity and specificity for undecaprenyl monophosphate

2012

Patel, K.; Ciepichal, E.; Swiezewska, E.; Valvano, M.

Glycobiology

22

116-122

722529

21335454

A UDP-HexNAc:polyprenol-P GalNAc-1-P transferase (WecP) representing a new subgroup of the enzyme family

2011

Merino, S.; Jimenez, N.; Molero, R.; Bouamama, L.; Regué, M.; Tomas, J.M.

J. Bacteriol.

193

1943-1952

722541

22408159

Functional characterization of UDP-Glucose: Undecaprenyl-phosphate glucose-1-phosphate transferases of Escherichia coli and Caulobacter crescentus

2012

Patel, K.; Toh, E.; Fernandez, X.; Hanuszkiewicz, A.; Hardy, G.; Brun, Y.; Bernards, M.; Valvano, M.

J. Bacteriol.

194

2646-2657

723725

22811320

Characterization of the highly conserved VFMGD motif in a bacterial polyisoprenyl-phosphate N-acetylaminosugar-1-phosphate transferase

2012

Furlong, S.E.; Valvano, M.A.

Protein Sci.

21

1366-1375

725566

22337656

A high-throughput, homogeneous, fluorescence resonance energy transfer-based assay for phospho-N-acetylmuramoyl-pentapeptide translocase (MraY)

2012

Shapiro, A.B.; Jahic, H.; Gao, N.; Hajec, L.; Rivin, O.

J. Biomol. Screen.

17

662-672

737580

25415593

Assessing HTS performance using bioassay ontology: screening and analysis of a bacterial phospho-N-acetylmuramoyl-pentapeptide translocase campaign

2014

Moberg, A.; Zander Balderud, L.; Hansson, E.; Boyd, H.

Assay Drug Dev. Technol.

12

506-513

737788

27312048

Catalytic mechanism of MraY and WecA, two paralogues of the polyprenyl-phosphate N-acetylhexosamine 1-phosphate transferase superfamily

2016

Al-Dabbagh, B.; Olatunji, S.; Crouvoisier, M.; El Ghachi, M.; Blanot, D.; Mengin-Lecreulx, D.; Bouhss, A.

Biochimie

127

249-257

738596

23986448

Inhibition of the first step in synthesis of the mycobacterial cell wall core, catalyzed by the GlcNAc-1-phosphate transferase WecA, by the novel caprazamycin derivative CPZEN-45

2013

Ishizaki, Y.; Hayashi, C.; Inoue, K.; Igarashi, M.; Takahashi, Y.; Pujari, V.; Crick, D.C.; Brennan, P.J.; Nomoto, A.

J. Biol. Chem.

288

30309-30319

739417

26161781

The polymerization of Aeromonas hydrophila AH-3 O-antigen LPS: concerted action of WecP and Wzy

2015

Merino, S.; Gonzalez, V.; Tomas, J.M.

PLoS ONE

10

e0131905

Links to other databases for ditrans,polycis-undecaprenyl phosphate

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Show Links (1 entry)

ChEBI

PubChem