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• • Molecular Structure
  • Sum Formula
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  • Synonyms
  • InChIKey
  • Pathways
• Roles as Enzyme Ligand
• • In Vivo Substrate
  • In Vivo Product
  • Substrate
  • Product
  • Cofactor
  • Activator
  • Inhibitor
  • Metals and Ions
  • 3D Structure (PDB)
• Enzyme Kinetic Parameters
• • k_cat Value (Turnover Number)
  • K_M Value
  • K_i Value
  • IC₅₀ Value
• References & Links
• • References
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Ligand N-acetyl-D-mannosamine

Basic Ligand Information

Molecular Structure

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Roles as Enzyme Ligand

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

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Show Natural Substrate (8 entries)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.1.1.233

N-acetyl-D-mannosamine + NAD+ = N-acetyl-D-mannosaminolactone + NADH + H+

389506, 389505, 740014

-

2.5.1.56

N-acetyl-D-mannosamine + phosphoenolpyruvate + H2O = ?

135468, 637325, 637324, 637320

-

2.5.1.56

phosphoenolpyruvate + N-acetyl-D-mannosamine + H2O = phosphate + N-acetylneuraminate

737676, 739614, 737983, 738339

-

2.5.1.56

phosphoenolpyruvate + N-acetyl-D-mannosamine + H2O = N-acetylneuraminate + phosphate

707514

-

2.5.1.56

3 entries

2.7.1.60

ATP + N-acetyl-D-mannosamine = ADP + N-acetyl-D-mannosamine 6-phosphate

641732, 641731, 641740, 641735, 2280, 641729, 2269, 641700, 641738, 641739, 641730, 135465

-

4.1.3.3

N-Acetylmannosamine + pyruvate = ?

33330, 33337

-

4.1.3.3

N-acetyl-D-mannosamine + pyruvate = N-acetylneuraminate

727656, 726631

-

4.1.3.3

2 entries

5.1.3.8

N-acetyl-D-mannosamine = N-acetyl-D-glucosamine

701881, 701855, 652504

-

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

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Show Natural Product (9 entries)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

3.2.1.183

UDP-N-acetyl-alpha-D-glucosamine + H2O = N-acetyl-D-mannosamine + UDP

-

-

4.1.3.3

N-Acetylneuraminic acid = N-Acetyl-D-mannosamine + pyruvate

652833

-

4.1.3.3

N-acetyl-D-neuraminic acid = N-acetyl-D-mannosamine + pyruvate

-

-

4.1.3.3

N-acetylneuraminate = N-acetyl-D-mannosamine + pyruvate

-

-

5.1.3.14

UDP-N-acetyl-D-glucosamine = UDP + N-acetyl-D-mannosamine

-

-

5.1.3.14

UDP-GlcNAc + H2O = ManNAc + UDP

-

-

5.1.3.14

UDP-GlcNAc = ManNAc + UDP

-

-

5.1.3.14

UDP-N-acetyl-D-glucosamine + H2O = UDP + N-acetylmannosamine

-

-

4.1.3.3

3 entries

5.1.3.14

4 entries

5.1.3.8

N-acetyl-D-glucosamine = N-acetyl-D-mannosamine

-

-

Substrate in Enzyme-catalyzed Reactions (21 results)

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Show Substrate (21 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.1.1.233

N-acetyl-D-mannosamine + NAD+ = N-acetyl-D-mannosaminolactone + NADH + H+

389506, 389505, 740014

-

1.1.1.240

N-acetyl-D-mannosamine + NAD+ + H2O = N-acetyl-D-mannosaminate + NADH + H+

286366

-

1.1.3.29

N-acetyl-D-mannosamine + O2 = N-acetyl-D-mannosaminolactone + H2O2

389762

-

2.5.1.56

N-acetyl-D-mannosamine + phosphoenolpyruvate + H2O = N-acetylneuraminate + phosphate

637321, 637322, 637323, 135468, 637319, 671716, 637325, 637324, 687886, 637320, 637318

-

2.5.1.56

N-acetyl-D-mannosamine + phosphoenolpyruvate + H2O = ?

135468, 637325, 637324, 637320

-

2.5.1.56

phosphoenolpyruvate + N-acetyl-D-mannosamine + H2O = phosphate + N-acetylneuraminate

657851, 737676, 739614, 737983, 738339

-

2.5.1.56

phosphoenolpyruvate + N-acetyl-D-mannosamine + H2O = N-acetylneuraminate + phosphate

707514

-

2.7.1.162

ATP + N-acetyl-D-mannosamine = ?

677700

-

2.7.1.162

ATP + N-acetyl-D-mannosamine = ADP + ?

677700

-

2.7.1.162

ATP + N-acetyl-D-mannosamine = ADP + N-acetyl-alpha-D-mannosamine 1-phosphate

737343

-

2.5.1.56

4 entries

2.7.1.162

3 entries

2.7.1.59

ATP + N-acetyl-D-mannosamine = ADP + N-acetyl-D-mannosamine 6-phosphate

641700, 641694, 641697, 641701, 641698

-

2.7.1.60

ATP + N-acetyl-D-mannosamine = ADP + N-acetyl-D-mannosamine 6-phosphate

641732, 641731, 641740, 641735, 672131, 673693, 674638, 2280, 641729, 673676, 675445, 2269, 641700, 641738, 641739, 641730, 135465

-

2.7.1.60

ATP + N-acetyl-D-mannosamine = ADP + N-acetyl-D-mannosamine-6-phosphate

641732, 641731, 641740, 641735, 2269, 2280, 135465, 641700, 641729, 641730, 641738, 641739

-

2.7.1.60

2 entries

4.1.2.23

N-acetyl-D-mannosamine + pyruvate = D-sialic acid

715592

-

4.1.3.3

N-Acetyl-D-mannosamine + pyruvate = N-Acetylneuraminic acid

33314, 33330, 33333, 33337, 33319, 33315, 33316, 33327

-

4.1.3.3

N-Acetylmannosamine + pyruvate = ?

33330, 33337

-

4.1.3.3

N-acetyl-D-mannosamine + pyruvic acid = N-acetyl-D-neuraminic acid

658576

-

4.1.3.3

N-acetyl-D-mannosamine + pyruvate = N-acetyl-D-neuraminic acid

666750, 713852

-

4.1.3.3

N-acetylmannosamine + pyruvate = N-acetylneuraminic acid

715921

-

4.1.3.3

N-acetyl-D-mannosamine + pyruvate = N-acetylneuraminate

748534, 749312, 727656, 726631

-

4.1.3.3

6 entries

5.1.3.8

N-acetyl-D-mannosamine = N-acetyl-D-glucosamine

651762, 651778, 651782, 652504, 651758, 728018, 637322, 701881, 674371, 701855, 675440, 747680, 727105

-

Product in Enzyme-catalyzed Reactions (15 results)

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Show Product (15 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

3.2.1.183

UDP-N-acetyl-alpha-D-glucosamine + H2O = N-acetyl-D-mannosamine + UDP

-

-

3.2.1.25

Man-(beta1-4)ManNAc + H2O = mannose + ManNAc

136040

-

4.1.2.23

D-sialic acid = N-acetyl-D-mannosamine + pyruvate

-

-

4.1.3.3

N-Acetylneuraminic acid = N-Acetyl-D-mannosamine + pyruvate

652833, 653594, 33314, 33330, 33333, 33337, 650525, 650651, 651432, 33319, 33327, 651103, 652991, 650772

-

4.1.3.3

N-acetyl-D-neuraminic acid = N-acetyl-D-mannosamine + pyruvate

-

-

4.1.3.3

N-acetyl-neuraminic acid = N-acetyl-D-mannosamine + pyruvate

-

-

4.1.3.3

N-acetylneuraminate = N-acetyl-D-mannosamine + pyruvate

-

-

4.1.3.3

N-acetyl-D-neuraminic acid = pyruvate + N-acetyl-D-mannosamine

-

-

4.1.3.3

N-acetylneuraminic acid = N-acetylmannosamine + pyruvate

-

-

4.1.3.3

N-acetylneuraminic acid = pyruvate + N-acetyl-D-mannosamine

-

-

5.1.3.14

UDP-N-acetyl-D-glucosamine = UDP + N-acetyl-D-mannosamine

2262, 2276, 2275, 2259, 2260, 2261, 2263, 2264, 2268, 2257, 2258

-

5.1.3.14

UDP-GlcNAc + H2O = ManNAc + UDP

-

-

5.1.3.14

UDP-GlcNAc = ManNAc + UDP

-

-

5.1.3.14

UDP-N-acetyl-D-glucosamine + H2O = UDP + N-acetylmannosamine

-

-

4.1.3.3

7 entries

5.1.3.14

4 entries

5.1.3.8

N-acetyl-D-glucosamine = N-acetyl-D-mannosamine

-

-

Activator in Enzyme-catalyzed Reactions (1 result)

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Show Activating Compound (1 entry)

EC NUMBER

COMMENTARY

LITERATURE

ENZYME 3D STRUCTURE

3.2.1.18

stimulates neuraminidase synthesis and activity about 8fold after 24 h

728971

-

Inhibitor in Enzyme-catalyzed Reactions (9 results)

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Show Inhibitors (9 entries)

EC NUMBER

COMMENTARY

LITERATURE

ENZYME 3D STRUCTURE

1.1.1.336

0.07 mM, 50% inhibition

692855

-

2.7.1.1

-

640224

-

2.7.1.59

inhibits phosphorylation of D-glucose

641697

-

2.7.1.59

no inhibition of activity with N-acetyl-D-glucosamine

641701

-

2.7.1.59

2 entries

2.7.1.7

-

641892

-

3.2.1.50

competitive inhibition

208687

-

3.2.1.52

-

393507

-

3.2.1.52

with 10 mM 83% of activity remains

393692

-

3.2.1.52

2 entries

3.2.1.92

-

137009, 137011

-

Enzyme Kinetic Parameters

k_cat Value (Turnover Number) (13 results)

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Show Turnover Number (13 entries)

EC NUMBER

TURNOVER NUMBER [1/S]

TURNOVER NUMBER MAXIMUM [1/S]

COMMENTARY

LITERATURE

2.5.1.56

0.83

-

the reaction mixture contains 1 mM MgCl2 in 50 mM Tris-acetate buffer, pH 7.5, at 37°C

671716

2.5.1.56

3.72

-

pH 7.3, 30°C, recombinant enzyme

737983

2.5.1.56

19.9

-

pH 8.0, 37°C

657851

2.5.1.56

3 entries

4.1.2.23

1.1

-

in 50 mM Tris-HCl, pH 7.8, at 37°C

715592

4.1.3.3

2.4

-

mutant enzyme P193Y, at pH 7.0 and 37°C

749150

4.1.3.3

4.5

-

recombinant His-taggged enzyme, pH 7.0, 37°C

727656

4.1.3.3

4.6

-

wild type enzyme, at pH 7.0 and 37°C

749150

4.1.3.3

5.4

-

wild type enzyme, at pH 7.0 and 37°C

749150

4.1.3.3

5.67

-

at pH 7.5 and 37°C

749312

4.1.3.3

9

-

-

690576

4.1.3.3

11

-

-

690576

4.1.3.3

15.3

-

mutant enzyme G210S/Y213G, at pH 7.0 and 37°C

749150

4.1.3.3

40.67

-

at pH 8.5 and 37°C

749312

4.1.3.3

9 entries

K_M Value (59 results)

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Show KM Value (59 entries)

EC NUMBER

KM VALUE [MM]

KM VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

1.1.1.233

1

-

-

389505

1.1.1.233

1

-

value unchanged by cloning and expression in E. coli JM109

389506

1.1.1.233

2 entries

1.1.3.29

40

-

-

389762

2.5.1.56

5.6

-

pH 8.2, 37°C

637321

2.5.1.56

6.25

-

-

637318

2.5.1.56

6.25

-

pH 8.2, 37°C

637321

2.5.1.56

11.6

-

the reaction mixture contains 1 mM MgCl2 in 50 mM Tris-acetate buffer, pH 7.5, at 37°C

671716

2.5.1.56

17.6

-

pH 8.0, 37°C

657851

2.5.1.56

18

-

pH 7.3, 30°C, recombinant enzyme

737983

2.7.1.59

0.95

-

enzyme from liver, 32°C, pH 7.5

641697

2.7.1.59

1

-

enzyme from kidney, 32°C, pH 7.5

641697

2.7.1.59

1

-

37°C, pH 7.5

641700

2.7.1.60

0.093

-

pH 7.5, 37°C, hexamer

2280

2.7.1.60

0.121

-

pH 7.5, 37°C, dimer

2280

2.7.1.60

0.2

-

pH 8.1, 37°C

641730

2.7.1.60

0.75

-

pH 7.6, 37°C

641731

2.7.1.60

0.75

-

-

641732

2.5.1.56

6 entries

2.7.1.59

3 entries

2.7.1.60

5 entries

4.1.2.23

181

-

in 50 mM Tris-HCl, pH 7.8, at 37°C

715592

4.1.3.3

6.9

-

at pH 7.0 and 37°C

748534

4.1.3.3

7.7

-

-

33337

4.1.3.3

53.3

-

at pH 7.5 and 37°C

749312

4.1.3.3

92.1

-

at pH 8.5 and 37°C

749312

4.1.3.3

131.7

-

recombinant enzyme, pH and temperature not specified in the publication

727332

4.1.3.3

149

-

recombinant His-taggged enzyme, pH 7.0, 37°C

727656

4.1.3.3

160

-

pH 7.0, 37°C

713843

4.1.3.3

160

-

soluble enzyme, pH not specified in the publication, temperature not specified in the publication

714508

4.1.3.3

180

-

-

690576

4.1.3.3

220

-

-

690576

4.1.3.3

245

-

cross-linked enzyme aggregates, pH 7.5, 37°C

714508

4.1.3.3

272

-

wild type enzyme, at pH 7.0 and 37°C

749150

4.1.3.3

333

-

wild type enzyme, at pH 7.0 and 37°C

749150

4.1.3.3

915

-

mutant enzyme P193Y, at pH 7.0 and 37°C

749150

4.1.3.3

3200

-

mutant enzyme G210S/Y213G, at pH 7.0 and 37°C

749150

5.1.3.8

1.7

-

in presence of saturating concentrations of ATP

2427

5.1.3.8

3

-

-

2428

5.1.3.8

4.76

-

-

637322

5.1.3.8

6.3

-

-

2430

5.1.3.8

9

-

in absence of ATP

2427

5.1.3.8

9.2

-

R375K, in the presence of 1 mM ATP

675440

5.1.3.8

12.8

-

37°C, pH 7.5

651758

5.1.3.8

13.9

-

R375A, in the presence of 1 mM ATP

675440

5.1.3.8

14.8

-

wild type, at pH 7, in the presence of 1 mM ATP

675440

5.1.3.8

15.5

-

E218A, in the presence of 1 mM ATP

675440

5.1.3.8

15.6

-

wild type, at pH 8, in the presence of 1 mM ATP

675440

5.1.3.8

16.6

-

pH 7.5, 30°C

728018

5.1.3.8

16.7

-

pH 7.5, 30°C

728018

5.1.3.8

16.7

-

pH 7.5, 30°C, recombinant His6-tagged wild-type enzyme

747680

5.1.3.8

19.7

-

pH 7.5, 30°C

728018

5.1.3.8

21

-

E218D, in the presence of 1 mM ATP

675440

5.1.3.8

21.3

-

C370A, in the presence of 1 mM ATP

675440

5.1.3.8

25.4

-

-

674987

5.1.3.8

27.2

-

N179A, in the presence of 1 mM ATP

675440

5.1.3.8

30.1

-

pH 7.5, 30°C, recombinant His6-tagged mutant K157L

747680

5.1.3.8

31.6

-

pH 7.5, 30°C, recombinant His6-tagged mutant K151V

747680

5.1.3.8

32.7

-

wild type, at pH 9, in the presence of 1 mM ATP

675440

5.1.3.8

53.8

-

E242Q, in the presence of 1 mM ATP

675440

5.1.3.8

57.33

-

wild type, at pH 6 in the presence of 1 mM ATP

675440

5.1.3.8

67.9

-

pH 7.5, 30°C, recombinant His6-tagged mutant K155A

747680

5.1.3.8

211

-

pH 7.5, 30°C, recombinant His6-tagged mutant K160P

747680

4.1.3.3

15 entries

5.1.3.8

26 entries

K_i Value (2 results)

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Show KI Value (2 entries)

EC NUMBER

KI VALUE [MM]

KI VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

2.7.1.1

50

-

at 37°C, pH 7.4

640224

2.7.1.7

75

-

pH 7.5, 25°C

641892

References & Links

Literature References (112)

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Show Reference (112 entries)

BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

2257

-

UDP-N-acetyl-D-glucosamine 2'-epimerase

1966

Spivak, C.T.; Roseman, S.

Methods Enzymol.

9

612-615

2258

5417402

Studies on the mechanism of action of uridine diphosphate N-acetylglucosamine 2-epimerase

1970

Salo, W.L.; Fletcher, H.G.

Biochemistry

9

882-885

2259

4337336

Uridine diphosphate N-acetyl-D-glucosamine 2-epimerase from rat liver. I. Catalytic and regulatory properties

1972

Sommar, K.M.; Ellis, D.B.

Biochim. Biophys. Acta

268

581-589

2260

5063602

Uridine diphosphate N-acetyl-D-glucosamine 2-epimerase from rat liver. II. Studies on the mechanism of action

1972

Sommar, K.M.; Ellis, D.B.

Biochim. Biophys. Acta

268

590-595

2261

4770741

Purification and properties of UDP-N-acetylglucosamine 2'-epimerase from rat liver

1973

Kikuchi, K.; Tsuiki, S.

Biochim. Biophys. Acta

327

193-206

2262

1103893

Biosynthesis of uridine diphosphate N-acetyl-D-mannosaminuronic acid from uridine diphosphate N-acetyl-D-glucosamine in Escherichia coli: separation of enzymes responsible for epimerization and dehydrogenation

1975

Kawamura, T.; Ichihara, N.; Ishimoto, N.; Ito, E.

Biochem. Biophys. Res. Commun.

66

1506-1512

2263

795466

The incorporation of tritium from tritium-enriched water into UDP-N-acetylglucosamine and UDP-N-acetyl-mannosamine catalyzed by UDP-N-acetylglucosamine 2-epimerase from Escherichia coli

1976

Salo, W.L.

Biochim. Biophys. Acta

452

625-628

2264

418068

Enzymatic formation of uridine diphosphate N-acetyl-D-mannosamine

1978

Kawamura, T.; Kimura, M.; Yamamori, S.; Ito, E.

J. Biol. Chem.

253

3595-3601

2268

7048002

UDP-N-acetyl-D-glucosamine 2'-epimerase from Escherichia coli

1982

Kawamura, T.; Ishimoto, N.; Ito, E.

Methods Enzymol.

83

515-519

2269

6303311

Subcellular localization and tissue distribution of sialic acid precursor-forming enzymes

1983

Van Rinsum, J.; van Dijk, W.; Hooghwinkel, G.J.M.; Ferwerda, W.

Biochem. J.

210

21-28

2275

3740419

Identification of N-acetylhexosamines produced by enzymes of the N-acetylneuraminic acid metabolic pathway by borate complex anion-exchange chromatography of the corresponding N-acetylhexosaminitols

1986

Scocca, J.R.

Anal. Biochem.

156

61-66

2276

-

Enzymic formation and release of a stable glycal intermediate: the mechanism of the reaction catalyzed by UDP-N-acetylglucosamine 2-epimerase

1996

Sala, R.F.; Morgan, P.M.; Tanner, M.E.

J. Am. Chem. Soc.

118

3033-3034

2280

9305887

A bifunctional enzyme catalyzes the first two steps in N-acetylneuraminic acid biosynthesis of rat liver. Purification and characterization of UDP-N-acetylglucosamine 2-epimerase/N-acetylmannosamine kinase

1997

Hinderlich, S.; Stäsche, R.; Zeitler, R.; Reutter, W.

J. Biol. Chem.

272

24313-24318

2427

1128274

N-Acetylglucosamine 2-epimerase from hog kidney

1975

Datta, A.

Methods Enzymol.

41

407-412

2428

-

N-Acetylglucosamine 2-epimerase from hog kidney

1966

Ghosh, S.; Roseman, S.

Methods Enzymol.

8

191-195

2430

8663114

Molecular cloning and identification of N-acetyl-D-glucosamine 2-epimerase from porcine kidney as a renin-binding protein

1996

Maru, I.; Ohta, Y.; Murata, K.; Tsukada, Y.

J. Biol. Chem.

271

16294-16299

33314

6389524

Purification and properties of N-acetylneuraminate lyase from Escherichia coli

1984

Uchida, Y.; Tsukada, Y.; Sugimori, T.

J. Biochem.

96

507-522

33315

182637

Purification and characterization of N-acetylneuraminate lyase from Clostridium perfringens

1976

Nees, S.; Schauer, R.; Mayer, F.

Hoppe-Seyler's Z. Physiol. Chem.

357

839-853

33316

4339794

N-acetylneuraminic acid aldolase of Clostridium perfringens: purification, properties and mechanism of action

1972

DeVries, G.H.; Binkley, S.B.

Arch. Biochem. Biophys.

151

234-242

33319

5459552

Purification and properties of N-acetylneuraminate lyase from beef kidney cortex

1970

Sirbasku, D.A.; Binkley, S.B.

Biochim. Biophys. Acta

198

479-482

33327

6301475

Configuration of substrate and products of N-acetylneuraminate pyruvate-lyase from Clostridium perfringens

1983

Deijl, C.M.; Vliegenthart, J.F.G.

Biochem. Biophys. Res. Commun.

111

668-674

33330

13811398

The sialic acids. I. Structure and enzymatic synthesis of N-acetylneuraminic acid

1960

Comb, D.G.; Roseman, S.

J. Biol. Chem.

235

2529-2537

33333

8081752

The three-dimensional structure of N-acetylneuraminate lyase from Escherichia coli

1994

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