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Ligand N-acetyl-D-glucosamine

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Basic Ligand Information

Molecular Structure
Picture of N-acetyl-D-glucosamine (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
Molfile
C8H15NO6
N-acetyl-D-glucosamine
OVRNDRQMDRJTHS-RTRLPJTCSA-N
 Download
Synonyms:
2-acetamido-2-deoxy-D-glucose, 2-acetylamino-2-deoxy-D-glucose, acetyl-D-glucosamine, acetylglucosamine, D-GlcNAc, GlcNAc, N-acetyglucosamine, N-acetyl-D-glucosamine units, N-acetyl-D-glucosamine[side 1], N-acetyl-glucosamine, N-acetyl D-glucosamine, N-acetylD-glucosamine, N-acetylglucosamin, N-acetylglucosamine, N-acetyl glucosamine, N-acetylglucosamine[side 2]

Related pathways

Pathway Source
Pathways
KEGG
ABC transporters, Amino sugar and nucleotide sugar metabolism, Biosynthesis of nucleotide sugars, Phosphotransferase system (PTS)
MetaCyc
beta-1,4-D-mannosyl-N-acetyl-D-glucosamine degradation, chitin degradation I (archaea), chitin degradation II (Vibrio), chitin degradation III (Serratia), chitin derivatives degradation more

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (17 results)

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EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
N-acetyl-D-glucosamine + NAD+ = N-acetyl-D-glucosaminate + NADH
show the reaction diagram
-
N-acetyl-D-glucosamine + O2 = ? + H2O2
show the reaction diagram
-
N-acetyl-D-glucosamine + alpha-D-mannose 1-phosphate = 4-O-beta-D-mannosyl-N-acetyl-D-glucosamine + phosphate
show the reaction diagram
-
N-acetyl-D-glucosamine + glycoprotein bound to polysaccharide cell wall = ?
show the reaction diagram
-
ATP + N-acetyl-D-glucosamine = ADP + N-acetyl-alpha-D-glucosamine 1-phosphate
show the reaction diagram
-
[protein]-Npi-phospho-L-histidine + N-acetyl-D-glucosamine[side 1] = [protein]-L-histidine + N-acetyl-D-glucosamine 6-phosphate[side2]
show the reaction diagram
-
ATP + N-acetyl-D-glucosamine = ADP + N-acetyl-D-glucosamine 1-phosphate
show the reaction diagram
-
ATP + N-acetyl-D-glucosamine = ADP + N-acetyl-D-glucosamine 6-phosphate
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
-
N-acetyl-D-glucosamine = N-acetyl-D-mannosamine
show the reaction diagram
-

In Vivo Product in Enzyme-catalyzed Reactions (20 results)

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EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
acetyl-CoA + D-glucosamine = CoA + N-acetyl-D-glucosamine
show the reaction diagram
486751, -
-
N,N'-diacetylchitobiose + phosphate = N-acetyl-D-glucosamine + N-acetyl-alpha-D-glucosamine 1-phosphate
show the reaction diagram
-
-
N-acetyl-D-glucosamine 6-sulfate units + H2O = N-acetyl-D-glucosamine units + sulfate
show the reaction diagram
-
-
chitosan + H2O = N-acetyl-D-glucosamine + ?
show the reaction diagram
-
-
N-acetylglucosamine oligomers + H2O = N-acetylglucosamine
show the reaction diagram
-
-
4-O-beta-D-galactopyranosyl-D-N-acetylglucosamine + H2O = beta-D-galactose + N-acetylglucosamine
show the reaction diagram
-
GlcNAc-beta-(1->4)-Mur2Acoyl-L-Ala-gamma-D-Glu = N-acetyl-D-glucosamine + 1,6-anhydro-N-acetylmuramoyl-L-Ala-gamma-D-Glu
show the reaction diagram
-
-
N-acetyl-D-mannosamine = N-acetyl-D-glucosamine
show the reaction diagram
652504, -
-

Substrate in Enzyme-catalyzed Reactions (81 results)

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EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
N-acetyl-D-glucosamine + NAD+ = N-acetyl-D-glucosaminate + NADH
show the reaction diagram
-
N-acetyl-D-glucosamine + O2 = N-acetyl-D-glucosaminate + H2O2
show the reaction diagram
-
N-acetyl-D-glucosamine + O2 = ? + H2O2
show the reaction diagram
-
N-acetyl-D-glucosamine + 10-deacetylbaccatin III = D-glucosamine + baccatin III
show the reaction diagram
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N-acetyl-D-glucosamine + tobramycin = D-glucosamine + N2'-acetyltobramycin
show the reaction diagram
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UDP-galactose + N-acetyl-D-glucosamine = UDP + beta-D-galactosyl-1,3-N-acetyl-D-glucosamine
show the reaction diagram
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UDP-GlcNAc + GlcNAc = UDP + N-acetyl-beta-D-glucosaminyl-1,3-N-acetyl-beta-D-galactosamine
show the reaction diagram
-
starch + 2-acetamido-2-deoxy-D-glucose = ?
show the reaction diagram
-
starch + N-acetyl-D-glucosamine = oligosaccharides terminated by 4-O-alpha-D-glucopyranosyl-N-acetyl-D-glucosamine
show the reaction diagram
-
N-acetyl-D-glucosamine + N-acetyl-alpha-D-glucosamine 1-phosphate = N,N'-diacetylchitobiose + phosphate
show the reaction diagram
-
N-acetyl-D-glucosamine + alpha-D-mannose 1-phosphate = 4-O-beta-D-mannopyranosyl-N-acetyl-D-glucosamine + phosphate
show the reaction diagram
-
N-acetyl-D-glucosamine + alpha-D-glucose 1-phosphate = 3-beta-D-glucosyl-N-acetyl-D-glucosamine + phosphate
show the reaction diagram
-
N-acetyl-D-glucosamine + glycoprotein bound to polysaccharide cell wall = ?
show the reaction diagram
-
phosphohistidinoprotein + N-acetyl-D-glucosamine = histidine-containing protein + N-acetyl-D-glucosamine phosphate
show the reaction diagram
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ADP + N-acetyl-D-glucosamine = AMP + N-acetyl-D-glucosamine 6-phosphate
show the reaction diagram
-
ATP + N-acetyl-D-glucosamine = ADP + N-acetyl-alpha-D-glucosamine 1-phosphate
show the reaction diagram
-
[protein]-Npi-phospho-L-histidine + N-acetyl-D-glucosamine[side 1] = [protein]-L-histidine + N-acetyl-D-glucosamine 6-phosphate[side2]
show the reaction diagram
-
ATP + N-acetyl-D-glucosamine = ADP + N-acetyl-D-glucosamine 1-phosphate
show the reaction diagram
-
ATP + N-acetyl-D-glucosamine = ADP + N-acetyl-D-glucosamine 6-phosphate
show the reaction diagram
-
N-acetylglucosamine + acetyl phosphate = ?
show the reaction diagram
-
N-acetylglucosamine + H2O = glucosamine + acetate
show the reaction diagram
-
N-acetyl glucosamine + H2O = ? + acetate
show the reaction diagram
-
D-glucosamine + N-acetyl-D-glucosamine = chitodimer
show the reaction diagram
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N-acetyl-D-glucosamine + melibiose = 6-O-alpha-D-galactosyl-N-acetyl-D-glucosamine + H2O
show the reaction diagram
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4-O-beta-D-mannopyranosyl-D-mannopyranose + N-acetyl-D-glucosamine = ?
show the reaction diagram
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N-acetyl-D-glucosamine + lactose = 4-O-beta-D-galactopyranosyl-N-acetyl-D-glucosamine + D-glucose
show the reaction diagram
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N-acetylglucosamine + H2O = ?
show the reaction diagram
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N-acetyl-D-glucosamine + H2O = D-glucosamine + acetate
show the reaction diagram
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N-acetylglucosamine + H2O = D-glucosamine + acetate
show the reaction diagram
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N-acetyl-D-glucosamine + H2O = D-glucosamine + acetate
show the reaction diagram
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N-Acetyl-D-glucosamine = ?
show the reaction diagram
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N-acetyl-D-glucosamine = N-acetyl-D-mannosamine
show the reaction diagram
-

Product in Enzyme-catalyzed Reactions (219 results)

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EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
acetyl-CoA + D-glucosamine = CoA + N-acetyl-D-glucosamine
show the reaction diagram
-
-
UDP-GlcNAc + H2O = UDP + GlcNAc
show the reaction diagram
-
-
N,N'-diacetylchitobiose + phosphate = N-acetyl-D-glucosamine + N-acetyl-alpha-D-glucosamine 1-phosphate
show the reaction diagram
-
-
N-acetyl-D-glucosamine 6-phosphate + H2O = N-acetyl-D-glucosamine + phosphate
show the reaction diagram
-
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N-acetylglucosamine 1-phosphate + H2O = N-acetylglucosamine + phosphate
show the reaction diagram
-
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N-acetylglucosamine 6-phosphate + H2O = N-acetylglucosamine + phosphate
show the reaction diagram
-
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N-acetylglucosamine 4-sulfate + H2O = N-acetylglucosamine + sulfate
show the reaction diagram
-
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N-acetyl-D-glucosamine 6-sulfate + H2O = N-acetyl-D-glucosamine + sulfate
show the reaction diagram
-
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Fuc-alpha-(1-4)-GlcNAc + H2O = alpha-L-fucose + N-acetyl-D-glucosamine
show the reaction diagram
-
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chitosan + H2O = N-acetyl-D-glucosamine + ?
show the reaction diagram
-
-
4-nitrophenyl 2-acetamido-2-deoxy-1-thio-beta-D-glucopyranoside + H2O = 4-nitrobenzenethiol + N-acetyl-D-glucosamine
show the reaction diagram
-
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GlcNbeta(1-4)GlcNAc + H2O = D-glucosamine + N-acetylglucosamine
show the reaction diagram
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N,N'-diacetyl-beta-chitobiose + H2O = N-acetyl-D-glucosamine
show the reaction diagram
-
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Galbeta1-3GlcNAc + H2O = beta-D-galactose + N-acetyl glucosamine
show the reaction diagram
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Man-(beta1-4)GlcNAc + H2O = mannose + GlcNAc
show the reaction diagram
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hyaluronan + H2O = N-acetylglucosamine + D-glucuronate + ?
show the reaction diagram
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N,N',N''-triacetyl-chitotriose + H2O = N,N'-diacetyl-chitobiose + N-acetyl-D-glucosamine
show the reaction diagram
-
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4-O-beta-D-galactopyranosyl-D-N-acetylglucosamine + H2O = beta-D-galactose + N-acetylglucosamine
show the reaction diagram
-
fucosyl-alpha-1,6-N-acetylglucosamine + H2O = fucose + N-acetylglucosamine
show the reaction diagram
-
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chitosan + H2O = N-acetyl-D-glucosamine + ?
show the reaction diagram
-
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1-beta-aspartyl-2-acetamido-1,2-dideoxy-D-glucosylamine + H2O = N-acetylglucosamine + asparagine
show the reaction diagram
171766, -
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GlcNAc-D-glucuronic acid-GlcNAc-D-glucuronic acid = DELTA-4,5-uronic acid-GlcNAc + N-acetyl-D-glucosamine + DELTA-4,5-glucuronic acid
show the reaction diagram
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GlcNAc-beta-(1->4)-Mur2Acoyl-L-Ala-gamma-D-Glu = N-acetyl-D-glucosamine + 1,6-anhydro-N-acetylmuramoyl-L-Ala-gamma-D-Glu
show the reaction diagram
-
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N-acetyl-D-mannosamine = N-acetyl-D-glucosamine
show the reaction diagram
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ATP + H2O + N-acetylglucosamine-[alpha-glucoside-binding protein][side 1] = ADP + phosphate + N-acetylglucosamine[side 2] + [alpha-glucoside-binding protein][side 1]
show the reaction diagram
-
-

Activator in Enzyme-catalyzed Reactions (20 results)

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EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
slight stimulation
-
slight activation
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stimulates neuraminidase synthesis and activity about 8fold after 24 h
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Inhibitor in Enzyme-catalyzed Reactions (61 results)

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EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
1.3 mM, 50% inhibition
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weak, 0.125 M
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inhibited by GlcNAc, but not by GalNAc
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weak
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39% inhibition at 25 mM
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5 mM, 17% inhibition
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binding energy -5.6 kcal/mol
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Enzyme Kinetic Parameters

kcat Value (Turnover Number) (72 results)

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EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
655
-
-
6.54
-
mutant enzyme Y648V, at pH 6.0 and 37°C
15.8
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apparent value, pH 6.5, 37°C, synthetic reaction, cosubstrate alpha-D-mannose 1-phosphate
6.64
-
pH not specified in the publication, temperature not specified in the publication

KM Value (161 results)

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EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
5.3
-
-
0.24
-
-
0.25
-
-
3.1
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reaction with UDP-N-acetyl-D-glucosamine
17.4
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mutant enzyme Y648V, at pH 6.0 and 37°C
1
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pH 7.0, 30°C, reverse phosphorolysis reaction
107
-
apparent value, pH 6.5, 37°C, synthetic reaction, cosubstrate alpha-D-mannose 1-phosphate
0.177
-
pH not specified in the publication, temperature not specified in the publication

Ki Value (11 results)

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EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.0009
-
for reaction with glucose, 30°C, pH 7.4
0.0657
-
pH not specified in the publication, temperature not specified in the publication

IC50 Value (1 result)

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EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
COMMENTARY
LITERATURE

References & Links

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Links to other databases for N-acetyl-D-glucosamine

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EXTERNAL LINKS
ChEBI
PubChem
UniChem