Ligand UDP-N-acetyl-D-galactosamine

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Basic Ligand Information

Molecular Structure
Picture of UDP-N-acetyl-D-galactosamine (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C17H27N3O17P2
UDP-N-acetyl-D-galactosamine
LFTYTUAZOPRMMI-NESSUJCYSA-N
Synonyms:
GalNAc alpha-UDP, UDP-2-deoxy-2-acetylamino-alpha-D-galactopyranose, UDP-alpha-GalNAc, UDP-alpha-N-acetyl-D-galactosamine, UDP-GalNAc, UDP-N-acetyl-2-deoxy-2-amino-alpha-D-galactopyranose, UDP-N-acetyl-alpha-D-galactosamine, UDP-N-acetyl-D-galactoseamine, UDP-N-acetyl-galactosamine, UDP-N-acetylgalactosamine, UDP-N-acetyl galactosamine, uridine diphosphoacetylgalactosamine


Show all pahtways known for Show all BRENDA pathways known for UDP-N-acetyl-D-galactosamine

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (56 results)

EC NUMBER
LITERATURE
REACTION DIAGRAM
PROVEN IN VIVO REACTION
ENZYME 3D STRUCTURE
show the reaction diagram
UDP-N-acetyl-alpha-D-galactosamine + N,N'-diacetyl-alpha-D-bacillosaminyl-diphospho-tritrans,heptacis-undecaprenol = UDP + N-acetyl-D-galactosaminyl-alpha-(1->3)-N,N'-diacetyl-alpha-D-bacillosaminyl-diphospho-tritrans,heptacis-undecaprenol
-
show the reaction diagram
UDP-N-acetyl-alpha-D-galactosamine + N-acetyl-D-galactosaminyl-alpha-(1->3)-N,N'-diacetyl-alpha-D-bacillosaminyl-diphospho-tritrans,heptacis-undecaprenol = UDP + N-acetyl-D-galactosaminyl-alpha-(1->4)-N-acetyl-D-galactosaminyl-alpha-(1->3)-N,N'-diacetyl-alpha-D-bacillosaminyl-diphospho-tritrans,heptacis-undecaprenol
-
show the reaction diagram
UDP-N-acetyl-alpha-D-galactosamine + N-acetyl-alpha-D-galactosaminyl-diphospho-ditrans,octacis-undecaprenol = UDP + alpha-D-GalNAc-(1->3)-alpha-D-GalNAc-diphospho-ditrans,octacis-undecaprenol
-
show the reaction diagram
UDP-N-acetyl-alpha-D-galactosamine + 3-O-[N-acetyl-beta-D-glucosaminyl-(1->4)-alpha-D-mannosyl]-L-threonyl-[protein] = UDP + 3-O-[N-acetyl-beta-D-galactosaminyl-(1->3)-N-acetyl-beta-D-glucosaminyl-(1->4)-alpha-D-mannosyl]-L-threonyl-[protein]
-
show the reaction diagram
UDP-N-acetyl-alpha-D-galactosamine + ditrans,octacis-undecaprenyl phosphate = UMP + N-acetyl-alpha-D-galactosaminyl-diphospho-ditrans,octacis-undecaprenol
-
show the reaction diagram
UDP-N-acetyl-alpha-D-galactosamine + H2O = N-acetyl-alpha-D-galactosaminyl-1-phosphate + UMP
-
show the reaction diagram
UDP-GalNAc = UDP-GlcNAc
-
show the reaction diagram
UDP-N-acetyl-2-deoxy-2-amino-alpha-D-galactopyranose = UDP-N-acetyl-2-deoxy-2-amino-alpha-D-galactofuranose
-

In Vivo Product in Enzyme-catalyzed Reactions (10 results)

EC NUMBER
LITERATURE
REACTION DIAGRAM
PROVEN IN VIVO REACTION
ENZYME 3D STRUCTURE
-
show the reaction diagram
UTP + N-acetyl-alpha-D-galactosamine 1-phosphate = diphosphate + UDP-N-acetyl-alpha-D-galactosamine
-
show the reaction diagram
UTP + N-acetyl-alpha-D-galactosamine 1-phosphate = diphosphate + UDP-N-acetyl-alpha-D-galactosamine
-

Substrate in Enzyme-catalyzed Reactions (718 results)

EC NUMBER
LITERATURE
REACTION DIAGRAM
REACTION
ENZYME 3D STRUCTURE
show the reaction diagram
(R)-3-hydroxydodecanoyl-[acyl-carrier protein] + UDP-N-acetyl-alpha-D-galactosamine = [acyl-carrier protein] + UDP-3-O-(3-hydroxydodecanoyl)-N-acetyl-alpha-D-galactosamine
-
show the reaction diagram
UDP-N-acetyl-alpha-D-galactosamine + D-fructose = UDP + beta-D-fructofuranosyl 2-(acetylamino)-2-deoxy-alpha-D-galactopyranoside
-
show the reaction diagram
UDP-N-acetyl-D-galactosamine + (N-acetyl-beta-D-glucosaminyl-1,2-alpha-D-mannosyl-1,3)-(N-acetyl-beta-D-glucosaminyl-1,2-alpha-D-mannosyl-1,6)-beta-D-mannosyl-1,4-N-acetyl-beta-D-glucosaminyl-R = UDP + N-acetyl-beta-D-glucosaminyl-1,2-alpha-D-mannosyl-1,3-(N-acetyl-beta-D-glucosaminyl-1,2-alpha-D-mannosyl-1,6)-(N-acetyl-beta-D-galactosaminyl-1,4)-beta-D-mannosyl-1,4-N-acetyl-beta-D-glucosaminyl-R
-
show the reaction diagram
UDP-GalNAc + 4-nitrophenyl-GlcAc = UDP + ?
show the reaction diagram
UDP-N-acetyl-alpha-D-galactosamine + N,N'-diacetyl-alpha-D-bacillosaminyl-diphospho-tritrans,heptacis-undecaprenol = UDP + N-acetyl-D-galactosaminyl-alpha-(1->3)-N,N'-diacetyl-alpha-D-bacillosaminyl-diphospho-tritrans,heptacis-undecaprenol
-
show the reaction diagram
UDP-N-acetyl-alpha-D-galactosamine + N-acetyl-D-galactosaminyl-alpha-(1->3)-N,N'-diacetyl-alpha-D-bacillosaminyl-diphospho-tritrans,heptacis-undecaprenol = UDP + N-acetyl-D-galactosaminyl-alpha-(1->4)-N-acetyl-D-galactosaminyl-alpha-(1->3)-N,N'-diacetyl-alpha-D-bacillosaminyl-diphospho-tritrans,heptacis-undecaprenol
-
show the reaction diagram
UDP-GalNAc + GlcNAc = ?
show the reaction diagram
UDP-N-acetyl-D-galactosamine + lipooligosacccharide = UDP + N-acetyl-D-galactosaminyllipooligosaccharide
-
show the reaction diagram
UDP-GalNAc + GlcNAc = ?
-
show the reaction diagram
diphosphate + UDP-N-acetyl-alpha-D-galactosamine = UTP + N-acetyl-alpha-D-galactosamine 1-phosphate
-
show the reaction diagram
UDP-galactose + UDP-N-acetyl-D-galactosamine = UMP + UDP-N-acetyl-6-(D-galactose-1-phospho)-D-galactosamine
-
show the reaction diagram
UDP-N-acetyl-alpha-D-galactosamine + ditrans,octacis-undecaprenyl phosphate = UMP + N-acetyl-alpha-D-galactosaminyl-diphospho-ditrans,octacis-undecaprenol
-
show the reaction diagram
UDP-N-acetyl-D-galactosamine + undecaprenyl phosphate = UMP + N-acetyl-D-galactosaminyl-diphosphoundecaprenol
-
show the reaction diagram
UDP-N-acetyl-D-galactosamine = UMP + N-acetyl-D-galactosamine 1-phosphate
-
show the reaction diagram
UDP-N-acetyl-D-galactosamine + H2O = ?
-
show the reaction diagram
UDP-N-acetyl-alpha-D-galactosamine + H2O = N-acetyl-alpha-D-galactosaminyl-1-phosphate + UMP
-
show the reaction diagram
UDP-N-acetylgalactosamine = ?
-
show the reaction diagram
UDP-N-acetyl-2-deoxy-2-amino-alpha-D-galactopyranose = UDP-N-acetyl-2-deoxy-2-amino-alpha-D-galactofuranose
-

Product in Enzyme-catalyzed Reactions (20 results)

EC NUMBER
LITERATURE
REACTION DIAGRAM
REACTION
ENZYME 3D STRUCTURE
-
show the reaction diagram
UDP-alpha-D-glucose + N-acetyl-alpha-D-galactosamine 1-phosphate = alpha-D-glucose 1-phosphate + UDP-N-acetyl-alpha-D-galactosamine
-
-
show the reaction diagram
UDP-N-acetylgalactosamine-4-sulfate + H2O = UDP-N-acetylgalactosamine + sulfate
-
-
show the reaction diagram
UDP-N-acetylgalactosamine 6-sulfate + H2O = sulfate + UDP-N-acetylgalactosamine
-

Inhibitor in Enzyme-catalyzed Reactions (12 results)

COMMENTARY
EC NUMBER
LITERATURE
ENZYME 3D STRUCTURE
3 mM, reduces activity by 50%
-
weak
-
UMP and UDP-GalNAc are 100fold less potent than UDP, UTP, and UDP-GlcNAc
-
weak, competitive with respect to UDP-galactose
-
weak
-
91% inhibition of the recombinant enzyme at 0.2 mM
-
competitive, binding study
-

3D Structure of Enzyme-Ligand-Complex (PDB) (97 results)

EC NUMBER
ENZYME 3D STRUCTURE

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (29 results)

COMMENTARY
EC NUMBER
LITERATURE
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
kcat value not detected in 100 mM cacodylate buffer, pH 7.0 containing 10 mM MnCl2 and 0.2-6 microM purified fusion-beta1,4-GalT7
-999
-
pH 7.0, 25°C
355
-
-
0.005
-
wild-type enzyme
0.42
-
pH 7.0, 37°C, recombinant wild-type enzyme
5.1
-
pH 7.0, 37°C, recombinant mutant M214S
5
-
pH 7.0, 37°C, recombinant mutant M214G
4
-
mutant enzyme M214R
0.00016
-
mutant enzyme M214T
1.6
-
mutant enzyme M214V
0.37
-
-
0.0817
-
wild-type
0.292
-
G176R/P234S/S235G/M266L/A268G mutant
0.24
-
wild-type, pH 7.4, 37°C
0.813
-
pH 6.5, 37°C, wild-type enzyme
3.47
-
pH 6.5, 37°C, mutant enzyme W129R
2.79
-
pH 6.5, 37°C, mutant enzyme W129F
2.43
-
pH 6.5, 37°C, mutant enzyme W129A
0.8
-
pH 6.5, 37°C, mutant enzyme N126A
2.53
-
mutant SGG, lactose as acceptor, 37°C, MnCl2, 25 mM Tris-HCl, pH 7.0
0.4
-
mutant AGG, lactose as acceptor, 37°C, MnCl2, 25 mM Tris-HCl, pH 7.0
0.3
-
AGGL mutant, N-acetyllactosamine, pH 6, 30°C
0.045
-
AGGL mutant, lactose, pH 6, 30°C
0.095
-
pH 7.0, 80°C
38295
-
37°C
247.9
-
25°C, pH 8.0
0.12
-
MalE-Gne fusion protein
247.9
-
pH 7.0, 80°C
38295
-
recombinant enzyme, pH 7.0, 80°C
27671
-

KM Value (111 results)

COMMENTARY
EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
LITERATURE
KM value is not detected in 100 mM cacodylate buffer, pH 7.0 containing 10 mM MnCl2 and 0.2-6 microM purified fusion-beta1,4-GalT7
-999
-
recombinant enzyme
3.6
-
pH 6.2, 37°C
0.11
-
-
0.221
-
pH 7.0, 25°C
9.275
-
-
0.285
-
deletion construct with amino acids 68-354, pH 7.0, temperature not specified in the publication
0.045
-
mutant C80S/C196S, pH 7.0, temperature not specified in the publication
0.023
-
mutant C89S/C196S/C209S, pH 7.0, temperature not specified in the publication
0.78
-
with L-fucosyl-alpha-1,2-alpha-D-galactosyl-O(CH2)7CH3 as acceptor
0.3
-
with L-fucosyl-alpha-1,2-beta-D-galactosyl-O(CH2)7CH3 as acceptor
0.34
-
G176R/P234S/S235G/M266L/A268G mutant
3.74
-
mutant D302C, pH 7.0, 37°C
0.022
-
mutant E303A, pH 7.0, 37°C
0.03
-
mutant E303C, pH 7.0, 37°C
0.051
-
mutant E303D, pH 7.0, 37°C
0.086
-
mutant E303Q, pH 7.0, 37°C
0.05
-
pancreatic cancer cell line, distal colon
0.048
-
wild-type, pH 7.0, 37°C
0.0087
-
+/-0.001 mM, mutant GalNAc-T2-D458H, pH7.4
0.03
-
+/-0.001 mM, mutant GalNAc-T2-D541A, pH7.4
0.013
-
+/-0.002 mM, pH7.4
0.011
-
+/-0.1 mM, mutant W316Y, 1.8 times higher than wild-type
9
-
+/-0.1 mM, mutant Y302L
5.2
-
+/-0.3 mM, mutant Y309L, 3.2 times higher than wild-type
16
-
+/-0.6 mM, mutant F325L, 1.2 times higher than wild-type
6.2
-
+/-0.7 mM, mutant W316F, 1.8 times higher than wild-type
9.1
-
+/-0.8 mM, truncated wild-type P-T1/delta42
5.1
-
+/-1.1 mM, mutant F303L, 2.8 times higher than wild-type
14.2
-
determination of Km for UDP-GalNAc is performed with saturating concentration of CPPTPSATTPAPPSSSAPPETTAA as substrate. No incorporation is found with UDP-Gal or UDP-GlcNAc
0.16
-
GalNAc-T1
0.062
-
GalNac-T1 mutant F457A
5.4
-
GalNac-T1 mutant G455Q
4
-
GalNac-T1 mutant N465A
3.6
-
GalNac-T1 mutant Q466A
6.1
-
GalNac-T1 mutants D444A and P-deltaN42
5.1
-
GalNac-T1 triple mutant D444A/D484A/D525A
4.4
-
GalNAc-T2
0.01
-
GalNAc-T3
0.029
-
ovine apomucin
0.006
-
pH 6.5, 37°C, mutant enzyme N126A
0.044
-
pH 6.5, 37°C, mutant enzyme W129A
0.029
-
pH 6.5, 37°C, mutant enzyme W129F
0.014
-
pH 6.5, 37°C, mutant enzyme W129R
0.017
-
pH 6.5, 37°C, wild-type enzyme
0.008
-
pH 7.0, 37°C
pH 7.2, 25°C
0.0107
-
pH 7.4, 37°C, enzyme form pp-GalNAc-T15
0.016
-
pH 7.4, 37°C, enzyme form pp-GalNAc-T2
0.081
-
pH 7.5, 23°C
0.052
-
wild-type, pH 7.4, 37°C
0.03
-
with polypeptide Muc2 as cosubstrate, at pH 6.0 and 37°C
0.046
-
AGGL mutant, lactose, pH 6, 30°C
0.25
-
AGGL mutant, N-acetyllactosamine, pH 6, 30°C
0.64
-
mutant AGG ka, lactose as acceptor, 37°C, MnCl2, 25 mM Tris-HCl, pH 7.0
0.5
-
mutant AGG kia, lactose as acceptor, 37°C, MnCl2, 25 mM Tris-HCl, pH 7.0
0.068
-
mutant AGG kib, lactose as acceptor, 37°C, MnCl2, 25 mM Tris-HCl, pH 7.0
36.1
-
mutant SGG ka, lactose as acceptor, 37°C, MnCl2, 25 mM Tris-HCl, pH 7.0
0.74
-
mutant SGG kia, lactose as acceptor, 37°C, MnCl2, 25 mM Tris-HCl, pH 7.0
0.101
-
mutant SGG kib, lactose as acceptor, 37°C, MnCl2, 25 mM Tris-HCl, pH 7.0
45.8
-
cosubstrate GM3
0.026
-
cosubstrate SM3
0.082
-
pH 7.0, 37°C
1.64
-
pH 7.3, 37°C, membrane-bound complete enzyme
0.19
-
pH 7.3, 37°C, soluble domain
0.097
-
pH 7.6, 37°C
pH 8.5, 37°C, 5 mM diphosphate
2.2
-
wild type protein, pH 8.0, 30°C
-
0.067
-
in the presence of B4 lectin from Vicia villosa
0.002
0.05
37°C
1.07
-
pH 7.0, 80°C
1.06
-
pH 8.0, 25°C
0.16
-
-
0.0114
-
MalE-Gne fusion protein
1.07
-
pH 7.0, 80°C
1.06
-
pH 8.0, 37°C
0.131
-
recombinant enzyme, pH 7.0, 80°C
2.4
-
Vmax 1.02 mM/min
0.85
-

Ki Value (1 result)

COMMENTARY
EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
LITERATURE
Ki value is above 9 mM, UDP-galactose 0.1-16 mM, 0-10 mM UDP-N-acetyl galactosamine
-999
-

IC50 Value (4 results)

COMMENTARY
EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
LITERATURE
-
0.016
-
GalNAc-MUC1 binding to biotinylated GalNAc-T2
65
-
GalNAc-MUC1 binding to biotinylated GalNAc-T4
30
-
GalNAc-MUC1 binding to biotinylated GalNAc-T4 lectin domain
50
-

References & Links