print visible entries

print all entries

Ligand D-galactosamine

Basic Ligand Information

Molecular Structure

close all tables

open all tables

Roles as Enzyme Ligand

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

top print hide

Show Natural Substrate (1 entry)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.1.3.9

D-galactosamine + O2 = ? + H2O2

389862, 389880, 389881, 389882, 389866, 389851

-

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

top print hide

Show Natural Product (1 entry)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

7.5.2.11

ATP + H2O + D-galactosamine-[galactosamine-binding protein Avi_5305][side 1] = ADP + phosphate + D-galactosamine[side 2] + [galactosamine-binding protein Avi_5305][side 1]

-

-

Substrate in Enzyme-catalyzed Reactions (11 results)

top print hide

Show Substrate (11 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.1.1.121

D-galactosamine + NAD+ = ? + NADH + H+

697263

-

1.1.1.121

D-galactosamine + NAD+ = D-galactosamino-delta-lactone + NADH + H+

747502

-

1.1.1.121

2 entries

1.1.3.29

D-galactosamine + O2 = ?

389762

-

1.1.3.9

D-galactosamine + O2 = ? + H2O2

389862, 389880, 389881, 389882, 389866, 389851

-

2.3.1.3

acetyl-CoA + galactosamine = CoA + N-acetyl-D-galactosamine

486750

-

2.7.1.162

ATP + D-galactosamine = ADP + D-galactosamine 1-phosphate

737343

-

2.7.1.6

2-amino-2-deoxy-D-galactose + ATP = 2-amino-2-deoxy-D-galactose 1-phosphate + ADP

704761

-

2.7.1.6

ATP + 2-amino-2-deoxy-D-galactose = ADP + 2-amino-2-deoxy-D-galactose 1-phosphate

641723

-

2.7.1.6

ATP + D-galactosamine = ADP + alpha-D-galactosamine 1-phosphate

759055, 721979, 759058

-

2.7.1.6

ATP + D-galactosamine = ADP + D-galactosamine 1-phosphate

661485, 641709, 641716, 758896, 759133, 759002, 641711

-

2.7.1.6

D-galactosamine + ATP = ?

704761

-

2.7.1.6

5 entries

Product in Enzyme-catalyzed Reactions (5 results)

top print hide

Show Product (5 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

3.1.6.4

galactosamine 6-sulfate + H2O = galactosamine + sulfate

-

-

3.2.1.109

polygalactosaminoglycan + H2O = galactosamine + GalNalpha1-4GalN + GalNalpha1-4GalNalpha1-4GalN + GalNalpha1-4GalNalpha1-4GalNalpha1-4GalN + GalNalpha1-4GalNalpha1-4GalNalpha1-4GalNalpha1-4GalN

, 135717

-

3.2.1.52

p-nitrophenyl galactosaminide + H2O = p-nitrophenol + galactosamine

-

-

3.5.1.33

N-acetyl-D-galactosamine + H2O = galactosamine + acetate

246601,

-

7.5.2.11

ATP + H2O + D-galactosamine-[galactosamine-binding protein Avi_5305][side 1] = ADP + phosphate + D-galactosamine[side 2] + [galactosamine-binding protein Avi_5305][side 1]

-

-

Activator in Enzyme-catalyzed Reactions (3 results)

top print hide

Show Activating Compound (3 entries)

EC NUMBER

COMMENTARY

LITERATURE

ENZYME 3D STRUCTURE

3.2.1.52

concentration of 100 mM: activity reaches 140%

393696

-

3.2.1.52

with 30 mM the activity of liver and brain enzymes reaches 135% and 114.3%

393668

-

3.2.1.52

2 entries

4.1.1.40

activates

4542

-

Inhibitor in Enzyme-catalyzed Reactions (13 results)

top print hide

Show Inhibitors (13 entries)

EC NUMBER

COMMENTARY

LITERATURE

ENZYME 3D STRUCTURE

1.1.3.9

competitive inhibition

389880

-

1.4.3.21

-

688483

-

2.4.1.37

-

735779

-

2.4.1.5

complete inhibition at 1% versus 1% sucrose

735553

-

2.7.7.9

-

643748

-

3.2.1.14

-

393548

-

3.2.1.23

-

706624

-

3.2.1.23

-

171353

-

3.2.1.52

-

393715

-

3.2.1.52

competitive inhibitor, less potent than glucosamine

393652

-

3.2.1.52

inhibits N-acetylhexosaminidase

136607

-

3.2.1.52

with 10 mM 84.0% of activity remains

393703

-

3.2.1.52

with 30 mM 84.3-89.3% of liver enzyme type A and 79.6-87.8% of liver enzyme type B remains

393668

-

3.2.1.23

2 entries

3.2.1.52

5 entries

Enzyme Kinetic Parameters

k_cat Value (Turnover Number) (11 results)

top print hide

Show Turnover Number (11 entries)

EC NUMBER

TURNOVER NUMBER [1/S]

TURNOVER NUMBER MAXIMUM [1/S]

COMMENTARY

LITERATURE

1.1.1.121

0.31

-

pH 7.4, 50°C

747502

1.1.1.121

0.3117

-

-

697263

2.7.1.6

0.195

-

-

641723

2.7.1.6

0.2

-

pH 7.5, 37°C, mutant enzyme Y379W

759055

2.7.1.6

0.3

-

pH 7.5, 37°C, mutant enzyme M60V/M185L/M180V/D268E/A334S/R366Q/G373S/Y379W

759055

2.7.1.6

1.7

-

pH 7.5, 37°C, wild-type enzyme

759055

2.7.1.6

2.1

-

pH 7.5, 37°C, wild-type enzyme

758896

2.7.1.6

3.4

-

pH 7.5, 37°C, mutant enzyme E245S

758896

2.7.1.6

4

-

pH 7.5, 37°C, mutant enzyme M60V/M180V/D268E/A334S/R366Q/G373S/Y379W

759055

2.7.1.6

18.1

-

pH 7.5, 37°C, mutant enzyme E244S

758896

2.7.1.6

25

-

pH 7.5, 37°C, mutant enzyme M185L/Y379W

759055

1.1.1.121

2 entries

2.7.1.6

9 entries

K_M Value (12 results)

top print hide

Show KM Value (12 entries)

EC NUMBER

KM VALUE [MM]

KM VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

1.1.1.121

2

3

-

697263

1.1.1.121

2

3

pH 7.4, 50°C

747502

1.1.1.121

2 entries

1.1.3.29

10

-

-

389762

2.7.1.6

0.22

-

pH 7.5, 37°C, mutant enzyme Y379W

759055

2.7.1.6

0.27

-

pH 7.5, 37°C, mutant enzyme M185L/Y379W

759055

2.7.1.6

0.62

-

pH 7.5, 37°C, mutant enzyme M60V/M185L/M180V/D268E/A334S/R366Q/G373S/Y379W

759055

2.7.1.6

0.71

-

pH 7.5, 37°C, wild-type enzyme

758896, 759055

2.7.1.6

0.92

-

pH 7.5, 37°C, mutant enzyme E244S

758896

2.7.1.6

1.2

-

pH 7.3, 25°C

641711

2.7.1.6

2.9

-

-

641723

2.7.1.6

2.9

-

pH 7.5, 37°C, mutant enzyme E245S

758896

2.7.1.6

4.8

-

pH 7.5, 37°C, mutant enzyme M60V/M180V/D268E/A334S/R366Q/G373S/Y379W

759055

2.7.1.6

9 entries

K_i Value (4 results)

top print hide

Show KI Value (4 entries)

EC NUMBER

KI VALUE [MM]

KI VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

1.1.3.9

0.073

-

-

389880

3.2.1.23

1

-

wild type enzyme, in 30 mM TES buffer, 145 mM NaCl, 0.01 mM Mg2+, pH 7.0 at 25°C

706624

3.2.1.23

1.3

-

mutant enzyme H418E, in 30 mM TES buffer, 145 mM NaCl, 0.01 mM Mg2+, pH 7.0 at 25°C

706624

3.2.1.23

1.4

-

mutant enzyme H418N, in 30 mM TES buffer, 145 mM NaCl, 0.01 mM Mg2+, pH 7.0 at 25°C

706624

3.2.1.23

3 entries

References & Links

Literature References (39)

top print hide

Show Reference (39 entries)

BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

4542

14186730

Nonoxidative decarboxylation of hydroxypyruvate in mammalian systems

1964

Hedrick, J.L.; Sallach, H.J.

Arch. Biochem. Biophys.

105

261-269

135717

-

Purification and some properties of the endo alpha-1,4 polygalactosaminidase from Pseudomonas sp.

1988

Tamura, J.i.; Takagi, H.; Kadowaki, K.

Agric. Biol. Chem.

52

2475-2484

136607

6055190

Isolation of beta-N-acetylhexosaminidase, beta-N-acetylglucosaminidase, and beta-N-acetylgalactosaminidase from calf brain

1967

Frohwein, Y.Z.; Gatt, S.

Biochemistry

6

2775-2782

171353

-

Purification and characterization of a thermostable beta-galactosidase with high transgalactosylation activity from Saccharopolyspora rectivirgula

1994

Nakao, M.; Harada, M.; Kodama, Y.; Nakayama, T.; Shibano, Y.; Amachi, T.

Appl. Microbiol. Biotechnol.

40

657-663

246601

13428742

Glucosamine metabolism. N-acetylglucosamine deacetylase

1957

Roseman, S.

J. Biol. Chem.

226

115-124

389762

-

Purification and properties of N-acyl-D-hexosamine oxidase from Pseudomonas sp. 15-1

1989

Horiuchi, T.

Agric. Biol. Chem.

53

361-368

389851

-

Expression and characterization of a recombinant Fusarium spp. galactose oxidase

2000

Xu, F.; Golightly, E.J.; Schneider, P.; Berka, R.M.; Brown, K.M.; Johnstone, J.A.; Baker, D.H.; Fuglsang, C.C.; Brown, S.H.; Svendsen, A.; Klotz, A.V.

Appl. Biochem. Biotechnol.

88

2332

389862

3813549

Purification and characterization of intracellular galactose oxidase from Dactylium dendroides

1987

Mendoca, M.H.; Zancan, G.T.

Arch. Biochem. Biophys.

252

507-514

389866

-

Kinetic properties of galactose oxidase from Gibberella fujikuroi

1984

Aisaka, K.; Uwajima, T.; Terada, O.

Agric. Biol. Chem.

48

1425-1431

389880

5752801

The inhibition of galactose oxidase

1968

Yip, M.C.M.; Dain, J.A.

Enzymologia

35

368-376

389881

-

Galactose oxidase of Polyporus circinatus

1966

Amaral, D.; Kelly-Falcoz, F.; Horecker, B.L.

Methods Enzymol.

9

87-92

389882

13863403

The D-galactose oxidase of Polyporus circinatus

1962

Avigad, G.; Amaral, D.; Asensio, C.; Horecker, B.L.

J. Biol. Chem.

237

2736-2743

393548

10792540

Production and characterization of a thermostable chitinase from a new alkalophilic Bacillus sp. BG-11

2000

Bhushan, B.

J. Appl. Microbiol.

88

800-808

393652

-

beta-N-Acetylhexosaminidase from soybean

1988

Gers-Barlag, H.; Bartz, I.; Ruediger, H.

Phytochemistry

27

3739-3741

393668

758959

Purification and some properties of liver and brain beta-N-acetyl-hexosaminidase S

1979

Potier, M.; Teitelbaum, J.; Melancon, S.B.; Dallaire, L.

Biochim. Biophys. Acta

566

80-87

393696

8085829

Purification and characterization of thermostable beta-N-acetylhexosaminidase of Bacillus stearothermophilus CH-4 isolated from chitin-containing compost

1994

Sakai, K.; Narihara, M.; Kasama, Y.; Wakayama, M.; Moriguchi, M.

Appl. Environ. Microbiol.

60

2911-2915

393703

-

Kinds of glycosidase and properties of beta-N-acetylglucosaminidase bound to mycelia of Streptomyces sp.

1987

Iwamoto, T.; Okiura, T.; Sasaki, T.; Inaoka, M.

J. Ferment. Technol.

65

593-596

393715

18192

Studies on the glycosidases of semen. Purification and properties of beta-N-acetylglucosaminidase from bull sperm

1977

Khar, A.; Anand, S.R.

Biochim. Biophys. Acta

483

141-151

486750

12980946

The acetylation of D-glucosamine by pigeon liver extracts

1957

Chou, T.C.; Soodak, M.

J. Biol. Chem.

196

105-109

641709

-

Galactokinase from pig liver

1975

Ballard, F.J.

Methods Enzymol.

42C

43-47

641711

6617655

Galactokinase of Vicia faba seeds

1983

Dey, P.M.

Eur. J. Biochem.

136

155-159

641716

7104394

Purification and properties of galactokinase from Tetrahymena thermophila

1982

Lavine, J.E.; Cantlay, E.; Roberts, C.T.; Morse, D.E.

Biochim. Biophys. Acta

717

76-85

641723

12816414

Studies on the substrate specificity of Escherichia coli galactokinase

2003

Yang, J.; Fu, X.; Jia, Q.; Shen, J.; Biggins, J.B.; Jiang, J.; Zhao, J.; Schmidt, J.J.; Wang, P.G.; Thorson, J.S.

Org. Lett.

5

2223-2226

643748

-

Uridine diphosphoryl glucose pyrophosphorylase

1973

Turnquist, R.L.; Hansen, R.G.

The Enzymes, 3rd. Ed. (Boyer, P. D. , ed. )

8

51-71

661485

15239057

Mechanistic implications of Escherichia coli galactokinase structure-based engineering

2004

Hoffmeister, D.; Thorson, J.S.

ChemBioChem

5

989-992

688483

17401531

Hydrogen peroxide derived from amine oxidation mediates the interaction between aminosugars and semicarbazide-sensitive amine oxidase

2007

O'Sullivan, J.; Davey, G.; OSullivan, M.; Tipton, K.F.

J. Neural Transm.

114

751-756

697263

18926808

Biochemical and structural characterization of a short-chain dehydrogenase/reductase of Thermus thermophilus HB8: a hyperthermostable aldose-1-dehydrogenase with broad substrate specificity

2009

Asada, Y.; Endo, S.; Inoue, Y.; Mamiya, H.; Hara, A.; Kunishima, N.; Matsunaga, T.

Chem. Biol. Interact.

178

117-126

704761

19433218

Functional studies of rat galactokinase

2009

Chu, X.; Li, N.; Liu, X.; Li, D.

J. Biotechnol.

141

142-146

706624

19472413

Direct and indirect roles of His-418 in metal binding and in the activity of beta-galactosidase (E. coli)

2009

Juers, D.H.; Rob, B.; Dugdale, M.L.; Rahimzadeh, N.; Giang, C.; Lee, M.; Matthews, B.W.; Huber, R.E.

Protein Sci.

18

1281-1292

721979

22633137

A highly efficient galactokinase from Bifidobacterium infantis with broad substrate specificity

2012

Li, L.; Liu, Y.; Wang, W.; Cheng, J.; Zhao, W.; Wang, P.

Carbohydr. Res.

355

35-39

735553

26016785

Comparison of inhibitory activity of bioactive molecules on the dextransucrase from Streptococcus mutans

2015

Lee, C.G.; Park, J.K.

Appl. Microbiol. Biotechnol.

99

7495-7503

735779

23754468

Thermodynamic signature of substrates and substrate analogs binding to human blood group B galactosyltransferase from isothermal titration calorimetry experiments

2013

Sindhuwinata, N.; Grimm, L.L.; Weissbach, S.; Zinn, S.; Munoz, E.; Palcic, M.M.; Peters, T.

Biopolymers

99

784-795

737343

24816108

Insights into the binding specificity and catalytic mechanism of N-acetylhexosamine 1-phosphate kinases through multiple reaction complexes

2014

Wang, K.C.; Lyu, S.Y.; Liu, Y.C.; Chang, C.Y.; Wu, C.J.; Li, T.L.

Acta Crystallogr. Sect. D

70

1401-1410

747502

18926808

Biochemical and structural characterization of a short-chain dehydrogenase/reductase of Thermus thermophilus HB8. A hyperthermostable aldose-1-dehydrogenase with broad substrate specificity

2009

Asada, Y.; Endo, S.; Inoue, Y.; Mamiya, H.; Hara, A.; Kunishima, N.; Matsunaga, T.

Chem. Biol. Interact.

178

117-126

758896

30253338

Modulation of the mobility of a key region in human galactokinase Impacts on catalysis and stability

2018

McAuley, M.; Huang, M.; Timson, D.J.

Bioorg. Chem.

81

649-657

759002

30593944

The characterisation of a galactokinase from Streptomyces coelicolor

2019

Keenan, T.; Mills, R.; Pocock, E.; Budhadev, D.; Parmeggiani, F.; Flitsch, S.; Fascione, M.

Carbohydr. Res.

472

132-137

759055

29505688

Improving the activity and stability of human galactokinase for therapeutic and biotechnological applications

2018

McAuley, M.; Mesa-Torres, N.; McFall, A.; Morris, S.; Huang, M.; Pey, A.L.; Timson, D.J.

ChemBioChem

19

1088-1095

759058

29193544

Characterisation of a bacterial galactokinase with high activity and broad substrate tolerance for chemoenzymatic synthesis of 6-aminogalactose-1-phosphate and analogues

2018

Huang, K.; Parmeggiani, F.; Pallister, E.; Huang, C.J.; Liu, F.F.; Li, Q.; Birmingham, W.R.; Both, P.; Thomas, B.; Liu, L.; Voglmeir, J.; Flitsch, S.L.

ChemBioChem

19

388-394

759133

32732027

Substrate specificity of the galactokinase from the human gut symbiont Akkermansia muciniphila ATCC BAA-835

2020

Zhang, X.; Sheng, W.; Li, K.; Rong, Y.; Wu, Q.; Meng, Q.; Kong, Y.; Chen, M.

Enzyme Microb. Technol.

139

109568

Links to other databases for D-galactosamine

top print hide

Show Links (1 entry)

ChEBI

PubChem

-