Ligand D-glucosamine

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Basic Ligand Information

Molecular Structure
Picture of D-glucosamine (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C6H13NO5
D-glucosamine
MSWZFWKMSRAUBD-IVMDWMLBSA-N
Synonyms:
2-amino-2-deoxy-D-glucopyranose, 2-amino-2-deoxy-D-glucose, D(+)-glucosamine, D-2-glucosamine, D-glucosaminate[side 1], D-glucosamine units, D-glucosamine[side 2], D-glucoseamine, glucosamine

Roles as Enzyme Ligand

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

EC NUMBER
LITERATURE
REACTION DIAGRAM
PROVEN IN VIVO REACTION
ENZYME 3D STRUCTURE
show the reaction diagram
acetyl-CoA + D-glucosamine = CoA + N-acetyl-D-glucosamine
-
show the reaction diagram
ADP + D-glucosamine = AMP + D-glucosamine 6-phosphate
-
show the reaction diagram
[protein]-Npi-phospho-L-histidine + D-glucosaminate[side 1] = [protein]-L-histidine + D-glucosaminate 6-phosphate[side 2]
-

In Vivo Product in Enzyme-catalyzed Reactions (7 results)

EC NUMBER
LITERATURE
REACTION DIAGRAM
PROVEN IN VIVO REACTION
ENZYME 3D STRUCTURE
-
show the reaction diagram
chitosan + H2O = D-glucosamine + ?
-
-
show the reaction diagram
N-acetyl-D-glucosamine + H2O = D-glucosamine + acetate
-
-
show the reaction diagram
N-acetyl-D-glucosamine + H2O = D-glucosamine + acetate
-
-
show the reaction diagram
ATP + H2O + D-glucosamine-[glucosamine-binding protein Avi_5305][side 1] = ADP + phosphate + D-glucosamine[side 2] + [glucosamine-binding protein Avi_5305][side 1]
-

Substrate in Enzyme-catalyzed Reactions (40 results)

EC NUMBER
LITERATURE
REACTION DIAGRAM
REACTION
ENZYME 3D STRUCTURE
show the reaction diagram
D-glucosamine + O2 = ?
-
show the reaction diagram
D-2-glucosamine + O2 = 2-amino-D-glucono-1,5-lactone + H2O2
-
show the reaction diagram
D-glucosamine + acceptor = 3-dehydro-D-glucosamine + reduced acceptor
-
show the reaction diagram
D-glucosamine + acceptor = ?
-
show the reaction diagram
acetyl-CoA + D-glucosamine = CoA + N-acetyl-D-glucosamine
-
show the reaction diagram
acetyl-CoA + D-glucosamine = CoA + N-acetyl-D-glucosamine
-
show the reaction diagram
acetyl-CoA + D-glucosamine = CoA + 6-O-acetyl-D-glucosamine
-
show the reaction diagram
starch + D-glucosamine = ?
-
show the reaction diagram
ADP + D-glucosamine = AMP + D-glucosamine 6-phosphate
-
show the reaction diagram
ATP + D-glucosamine = ADP + D-glucosamine 1-phosphate
-
show the reaction diagram
[protein]-Npi-phospho-L-histidine + D-glucosaminate[side 1] = [protein]-L-histidine + D-glucosaminate 6-phosphate[side 2]
-
show the reaction diagram
ATP + D-glucosamine = ADP + D-glucosamine 6-phosphate
-
show the reaction diagram
phosphoramidate + glucosamine = glucosamine 1-phosphate + NH3
-
show the reaction diagram
(phosphate)n + glucosamine = (phosphate)n-1 + D-glucosamine 6-phosphate
-
show the reaction diagram
ATP + D-glucosamine = ADP + D-glucosamine 6-phosphate
-

Product in Enzyme-catalyzed Reactions (66 results)

EC NUMBER
LITERATURE
REACTION DIAGRAM
REACTION
ENZYME 3D STRUCTURE
-
show the reaction diagram
D-glucosamino-1,5-lactone + reduced phenazine methosulfate = D-glucosamine + reduced phenazine methosulfate
-
-
show the reaction diagram
N-acetyl-D-glucosamine + 10-deacetylbaccatin III = D-glucosamine + baccatin III
-
-
show the reaction diagram
N-acetyl-D-glucosamine + tobramycin = D-glucosamine + N2'-acetyltobramycin
-
-
show the reaction diagram
glucosamine 6-phosphate + H2O = glucosamine + phosphate
-
-
show the reaction diagram
D-glucosamine 6-phosphate + H2O = D-glucosamine + phosphate
-
show the reaction diagram
D-glucosamine-6-phosphate + H2O = D-glucosamine + phosphate
-
-
show the reaction diagram
D-glucosamine 6-phosphate + H2O = D-glucosamine + phosphate
-
show the reaction diagram
glucosamine-N-sulfate + H2O = glucosamine + SO42-
-
show the reaction diagram
N2-sulfo-D-glucosamine 3-sulfate unit + H2O = D-glucosamine units + sulfate
-
-
show the reaction diagram
N-sulfo-D-glucosamine + H2O = D-glucosamine + sulfate
-
-
show the reaction diagram
4-methylumbelliferyl beta-D-glucosaminide + H2O = 4-methylumbelliferone + D-glucosamine
-
show the reaction diagram
p-nitrophenyl-2-amino-2-deoxy-D-glucoside + H2O = p-nitrophenol + 2-amino-2-deoxy-D-glucose
-
-
show the reaction diagram
4-methylumbelliferyl beta-D-glucosaminide + H2O = 4-methylumbelliferone + D-glucosamine
-
-
show the reaction diagram
N-acetyl-D-glucosamine + H2O = D-glucosamine + acetate
-
show the reaction diagram
N-acetylglucosamine + H2O = D-glucosamine + acetate
-
-
show the reaction diagram
L-aspartylglucosamine + H2O = L-aspartate + glucosamine
-
show the reaction diagram
N-acetyl-D-glucosamine + H2O = D-glucosamine + acetate
-
-
show the reaction diagram
ATP + H2O + D-glucosamine-[glucosamine-binding protein Avi_5305][side 1] = ADP + phosphate + D-glucosamine[side 2] + [glucosamine-binding protein Avi_5305][side 1]
-

Activator in Enzyme-catalyzed Reactions (9 results)

COMMENTARY
EC NUMBER
LITERATURE
ENZYME 3D STRUCTURE

Inhibitor in Enzyme-catalyzed Reactions (36 results)

COMMENTARY
EC NUMBER
LITERATURE
ENZYME 3D STRUCTURE
competitive inhibitor
-
the TGase 2 inhibitor, might be an attractive novel target for treatment of malignant cancers
-
high concentrations during cultivation
-
substrate inhibition
-
competitive with glucose
-
25-30% inhibition at 20 mM
-
complete inhibition at 1% versus 1% sucrose
-
20 mM, 67% inhibition
-
65% inhibition at 10 mM
-
competitive
-
inhibits activity at 10 mM, 60.7% relative activity compared with activity without any addition of effector
-
competitive inhibition, Ki = 2.8 mM
-
68% inhibition, recombinant enzyme
-
non-competitive inhibition
-
inhibition of CM-cellulase activity of enzyme E1, E3a, E3b and E4
-
with 30 mM 72.2-76.3% of liver enzyme type A and 65.7-73.3% of liver enzyme type B remains
-
1 mM, 22% inhibition
-
with 10 mM 29.3% of activity remains
-
inhibits N-acetylhexosaminidase
-
competitive inhibitor, more potent than galactosamine
-
competitive with UDP-N-acetylglucosamine
-

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (15 results)

COMMENTARY
EC NUMBER
LITERATURE
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
-
0.6217
-
pH 7.4, 50°C
0.62
-
pH 7.5, 70°C, mutant enzyme Y156A
104
-
pH 7.5, 70°C, mutant enzyme Y156K
117
-
pH 7.5, 70°C, wild-type enzyme
197
-
mutant enzyme C485A, at pH 6.0 and 37°C
35.4
-
pH 6.0, 37°C
9.56
-
wild type enzyme, at pH 6.0 and 37°C
9.56
-
pH 8.0, 37°C
237
-
at pH 7.5 and 80°C
120
-
pH 7.5, 70°C
120
-
pH 9.5, 30°C
293.5
-

KM Value (40 results)

COMMENTARY
EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
LITERATURE
-
139
-
pH 7.4, 50°C
139
-
pH 6.5
35
-
-
40
-
pH 7.5, 70°C, wild-type enzyme
0.00002
-
pH 7.5, 70°C, mutant enzyme Y156K
0.00002
-
pH 7.5, 70°C, mutant enzyme Y156A
0.00002
-
0.1 M ethanolamine buffer at pH 9.4
0.74
-
pH 7.3, 25°C
0.21
-
membrane-bound enzyme
0.24
-
CHAPS-solubilized enzyme
0.26
-
wild type enzyme, at pH 6.0 and 37°C
13.3
-
pH 6.0, 37°C
13.3
-
mutant enzyme C485A, at pH 6.0 and 37°C
58.1
-
pH 8.0, 37°C
15.6
-
pH 7.5, 50°C, ATP as phosphoryl donor
0.23
-
erythrocyte enzyme
2
-
hexokinase I, at 37°C, pH 8.1
0.6
-
hexokinase Ia
0.85
-
hexokinase Ia, at 37°C, pH 7.2
1.5
-
hexokinase III, at 30°C, pH 8.1
0.2
-
hexokinase Ib
1.3
-
90°C, pH 6.2
0.06
-
at 30°C, pH 7.5
0.06
-
at 30°C, pH 8.1
0.116
-
at 37°C, pH 8.1
0.4
-
hexokinases Ib and Ic, at 37°C, pH 7.2
0.5
-
at pH 7.5 and 80°C
0.33
-
pH 7.5, 70°C
0.33
-
pH 9.5, 30°C
1.1
-
pH 7.5, 25°C
5
-
pH 7.0, 25°C
0.48
-
pH and temperature not specified in the publication

Ki Value (11 results)

COMMENTARY
EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
LITERATURE
pH 6.5, 37°C
0.26
-
substrate 1-[4,4-difluoro-5,7-dimethyl-4-bora-3a,4a-diaza-s-indacene-3-propionyl-glycylamino]-beta-D-glucosamine, pH 6.5, 37°C
0.26
-
substrate 4-methylumbelliferyl-beta-D-glucosaminide, pH 6.5, 37°C
0.28
-
30°C, pH 6.6
46
-
fructose as substrate
at pH 7.5 and 80°C
60
-
pH 7.5, 70°C
60
-
pH 7.4, 22°C
0.1864
-
37°C, pH 7.8
0.01
-
-
2.8
-

IC50 Value (1 result)

COMMENTARY
EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
LITERATURE
-
30
-

References & Links

Links to other databases for D-glucosamine

ChEBI
PubChem
-
PubChem