Ligand UDP-alpha-D-galactose

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Basic Ligand Information

Molecular Structure

C₁₅H₂₄N₂O₁₇P₂

UDP-alpha-D-galactose

HSCJRCZFDFQWRP-ABVWGUQPSA-N

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Synonyms:

alpha-UDP-D-galactose, alpha-UDP-galactose, UDP-alpha-D-galactopyranose, UDP-D-galactopyranose, UDP-D-galactose, UDP-D-galactose-hexodialose, UDP-Gal, UDP-galactopyranose, UDP-galactose, UDPgalactose, UDP galactose, Uridine 5'-(trihydrogen diphosphate) P'-alpha-D-galactopyranosyl ester

Related pathways

BRENDA

degradation of hexoses, lipid A biosynthesis, O-antigen biosynthesis, sulfated glycosaminoglycan metabolism

KEGG

Amino sugar and nucleotide sugar metabolism, Biosynthesis of nucleotide sugars, Galactose metabolism, O-Antigen nucleotide sugar biosynthesis, Teichoic acid biosynthesis

MetaCyc

A series fagopyritols biosynthesis, ABH and Lewis epitopes biosynthesis from type 1 precursor disaccharide, ABH and Lewis epitopes biosynthesis from type 2 precursor disaccharide, acylated cyanidin galactoside biosynthesis, alpha-solanine/alpha-chaconine biosynthesis, alpha-tomatine biosynthesis, B series fagopyritols biosynthesis, biosynthesis of Lewis epitopes (H. pylori), colanic acid (Escherichia coli K12) biosynthesis, colanic acid building blocks biosynthesis, complex N-linked glycan biosynthesis (plants), complex N-linked glycan biosynthesis (vertebrates), D-galactose degradation I (Leloir pathway), D-galactose detoxification, Escherichia coli serotype O:104 O antigen biosynthesis, Escherichia coli serotype O:107 O antigen biosynthesis, Escherichia coli serotype O:111/Salmonella enterica serotype O:35 O antigen biosynthesis, Escherichia coli serotype O:117 O antigen biosynthesis, Escherichia coli serotype O:127 O antigen biosynthesis, Escherichia coli serotype O:128 O antigen biosynthesis, Escherichia coli serotype O:15 O antigen biosynthesis, Escherichia coli serotype O:169 O antigen biosynthesis, Escherichia coli serotype O:183/Shigella boydii serotype O:10 O antigen biosynthesis, Escherichia coli serotype O:1B/Salmonella enterica serotype O:42 O antigen biosynthesis, Escherichia coli serotype O:21/Salmonella enterica serotype O:38 O antigen biosynthesis, Escherichia coli serotype O:55/Salmonella enterica serotype O:50 O antigen biosynthesis, Escherichia coli serotype O:56 O antigen biosynthesis, Escherichia coli serotype O:7 O antigen biosynthesis, Escherichia coli serotype O:71/Salmonella enterica serotype O:28ac O antigen biosynthesis, Escherichia coli serotype O:85/Salmonella enterica serotype O:17 O antigen biosynthesis, Escherichia coli serotype O:86 O antigen biosynthesis, gala-series glycosphingolipids biosynthesis, galactolipid biosynthesis I, galactolipid biosynthesis II, ganglio-series glycosphingolipids biosynthesis, globo-series glycosphingolipids biosynthesis, glycosaminoglycan-protein linkage region biosynthesis, H. pylori 26695 O-antigen biosynthesis, hygromycin B biosynthesis, i antigen and I antigen biosynthesis, indole-3-acetate inactivation IX, isovitexin glycosides biosynthesis, kaempferol diglycoside biosynthesis (pollen-specific), lacto-series glycosphingolipids biosynthesis, lipid A-core biosynthesis (E. coli K-12), lipid A-core biosynthesis (H. pylori), lipid A-core biosynthesis (Salmonella), lychnose and isolychnose biosynthesis, mucin core 1 and core 2 O-glycosylation, mycolyl-arabinogalactan-peptidoglycan complex biosynthesis, neolacto-series glycosphingolipids biosynthesis, O-antigen building blocks biosynthesis (E. coli), Porphyromonas gingivalis O-LPS antigen biosynthesis, procollagen hydroxylation and glycosylation, protein O-glycosylation (Neisseria), quercetin diglycoside biosynthesis (pollen-specific), Salmonella enterica serotype O:13 O antigen biosynthesis, Salmonella enterica serotype O:2 O antigen biosynthesis, Salmonella enterica serotype O:3,10 O antigen biosynthesis, Salmonella enterica serotype O:4 O antigen biosynthesis (group B1), Salmonella enterica serotype O:8 O antigen biosynthesis, Salmonella enterica serotype O:9 O antigen biosynthesis, Salmonella enterica serotype O:9,46 O antigen biosynthesis, Salmonella enterica serotype O:9,46,27 O antigen biosynthesis, saponin biosynthesis II, Shigella boydii serotype 6 O antigen biosynthesis, solasodine glycosylation, soybean saponin I biosynthesis, stachyose biosynthesis, stachyose degradation, stellariose and mediose biosynthesis, succinoglycan biosynthesis, superpathway of UDP-glucose-derived O-antigen building blocks biosynthesis, terminal O-glycans residues modification (via type 2 precursor disaccharide), UDP-alpha-D-galactofuranose biosynthesis, UDP-alpha-D-galactose biosynthesis, xyloglucan biosynthesis

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Show all BRENDA pathways known for UDP-alpha-D-galactose

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Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (241 results)

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UDPgalactose + indol-3-ylacetyl-myo-inositol = UDP + 5-O-(indol-3-ylacetyl-myo-inositol) D-galactoside

488623

2.4.1.167

UDPgalactose + sucrose = UDP + 6F-alpha-galactosylsucrose

488686

2.4.1.179

UDP-galactose + D-galactosyl-1,4-beta-D-glucosyl-glycolipid = UDP + D-galactosyl-1,3-beta-D-galactosyl-1,4-beta-D-glucosyl-glycolipid

638379, 638380, 638381, 638376

2.4.1.205

UDPgalactose + galactogen = UDP + 1,6-beta-D-galactosylgalactogen

UDP-galactose + soyasapogenol B 3-O-beta-D-glucuronide = UDP + soyasaponin III

UDP-alpha-D-galactose + N-acetyl-beta-D-galactosaminyl-(1->3)-beta-D-galactosyl-(1->4)-beta-D-glucosyl-(1<->1)-ceramide = UDP + beta-D-galactosyl-(1->4)-N-acetyl-beta-D-galactosaminyl-(1->3)-beta-D-galactosyl-(1->4)-D-glucosyl-(1<->1)-ceramide

715438

2.4.1.294

UDP-alpha-D-galactose + cyanidin = UDP + cyanidin 3-O-beta-D-galactoside

720783

2.4.1.303

UDP-alpha-D-galactose + N-acetyl-alpha-D-glucosaminyl-diphospho-ditrans,octacis-undecaprenol = UDP + beta-D-Gal-beta-(1->3)-alpha-D-GlcNAc-diphospho-ditrans,octacis-undecaprenol

722373

2.4.1.304

UDP-alpha-D-galactose + N-acetyl-alpha-D-glucosaminyl-diphospho-ditrans,octacis-undecaprenol = UDP + beta-D-Gal-(1->4)-alpha-D-GlcNAc-diphospho-ditrans,octacis-undecaprenol

722531

2.4.1.309

UDP-alpha-D-galactose + alpha-L-Fuc-(1->2)-beta-D-Gal-(1->3)-alpha-D-GalNAc-(1->3)-alpha-D-GalNAc-diphospho-ditrans,octacis-undecaprenol = UDP + alpha-D-Gal-(1->3)-(alpha-L-Fuc-(1->2))-beta-D-Gal-(1->3)-alpha-D-GalNAc-(1->3)-alpha-D-GalNAc-diphospho-ditrans,octacis-undecaprenol

723245

2.4.1.343

UDP-alpha-D-galactose + N-acetyl-alpha-D-glucosaminyl-diphospho-ditrans,octacis-undecaprenol = UDP + alpha-D-Gal-(1->3)-alpha-D-GlcNAc-diphospho-ditrans,octacis-undecaprenol

UDP-alpha-D-galactose + [procollagen]-(5R)-5-O-(beta-D-galactosyl)-5-hydroxy-L-lysine = UDP + [procollagen]-(5R)-5-O-[alpha-D-galactosyl-(1->2)-beta-D-galactosyl]-5-hydroxy-L-lysine

777774

2.4.1.74

UDPgalactose + glycosaminoglycan = UDP + D-galactosylglycosaminoglycan

489374

2.4.1.86

UDPgalactose + N-acetyl-D-glucosaminyl-1,3-beta-D-galactosyl-1,4-D-glucosylceramide = UDP + 1,4-beta-D-galactosyl-N-acetyl-D-glucosaminyl-1,3-beta-D-galactosyl-1,4-D-glucosylceramide

639628, 639630, 639633

UDP-galactose + UDP-N-acetyl-D-glucosamine = UMP + UDP-N-acetyl-6-(D-galactose-1-phospho)-D-glucosamine

643759

3.6.1.9

UDP-alpha-D-galactose + H2O = UMP + alpha-D-galactose-1-phosphate

246823, 246827, 208391, 246806

In Vivo Product in Enzyme-catalyzed Reactions (25 results)

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2.7.7.10

UTP + alpha-D-galactose 1-phosphate = diphosphate + UDP-galactose

642821, 642813, -

Substrate in Enzyme-catalyzed Reactions (1698 results)

UDP-alpha-D-galactose + D-fructose = UDP + sucrose

UDP-Gal + Galbeta(1-3)Gal = Galbeta(1-3)Galbeta(1-3)Gal + UDP

UDPgalactose + indol-3-ylacetyl-myo-inositol = UDP + 5-O-(indol-3-ylacetyl-myo-inositol) D-galactoside

488623

2.4.1.167

UDPgalactose + sucrose = UDP + 6F-alpha-galactosylsucrose

UDP-alpha-D-galactose + naringenin = UDP + naringenin 7-O-beta-D-galactoside

777863

2.4.1.186

UDP-galactose + glycogenin = UDP + galactosylated glycogenin

638247

2.4.1.189

UDPgalactose + luteolin = UDP + luteolin 7-O-galactoside

488822

2.4.1.191

UDP-galactose + luteolin 7-O-[beta-D-glucuronosyl-1,2-beta-D-glucuronide] = UDP + luteolin 7-O-[beta-D-glucuronosyl-1,2-beta-D-glucuronide]-4'-O-beta-D-galactoside

488822

2.4.1.203

UDP-galactose + trans-zeatin = UDP + O-galactosylzeatin

UDP-galactose + (1,4-alpha-glucosyl)n = UDP + ?

660292

2.4.1.262

UDP-galactose + soyasapogenol B = ?

UDP-D-galactose + 2-deoxystreptamine = ?

719134

2.4.1.288

UDP-alpha-D-galactopyranose + methyl alpha-D-mannopyrannoside = UDP + ?

UDP-alpha-D-galactose + 1,2-diacyl-3-O-(alpha-D-glucopyranosyl)-sn-glycerol = 1,2-diacyl-3-O-[alpha-D-galactopyranosyl-(1->6)-O-alpha-D-glucopyranosyl]-sn-glycerol + UDP

727886

2.4.1.343

UDP-alpha-D-galactose + N-acetyl-alpha-D-glucosaminyl-diphospho-ditrans,octacis-undecaprenol = UDP + alpha-D-Gal-(1->3)-alpha-D-GlcNAc-diphospho-ditrans,octacis-undecaprenol

740263

2.4.1.35

UDP-galactose + sinapic acid = UDP + sinapoyl 3-O-beta-D-galactoside

UDP-alpha-D-galactose + [procollagen]-(5R)-5-O-(beta-D-galactosyl)-5-hydroxy-L-lysine = UDP + [procollagen]-(5R)-5-O-[alpha-D-galactosyl-(1->2)-beta-D-galactosyl]-5-hydroxy-L-lysine

UDP-galactose + p-nitrophenyl-GlcNAc = UDP + Gal-beta(1-4)GlcNAc-p-nitrophenyl

UDP-galactose + sucrose = UDP + loliose

660226

2.4.1.B78

UDP-galactose + kaempferol 3-O-glucoside = UDP + kaempferol 3-O-beta-D-galactosyl-(1->6)-beta-D-glucoside

758023

2.7.7.10

diphosphate + UDP-alpha-D-galactose = UTP + alpha-D-galactose 1-phosphate

642819

1GUP, 3D-view

2.7.7.12

alpha-D-glucose 1-phosphate + UDP-alpha-D-galactose = UDP-alpha-D-glucose + alpha-D-galactose 1-phosphate

723038, 737739

2.7.7.37

UDP-galactose + phosphate = UDP + D-galactose 1-phosphate

643249

2.7.7.69

UDP-alpha-D-galactose + phosphate = alpha-D-galactose 1-phosphate + UDP

676531

2.7.7.9

diphosphate + UDP-galactose = UTP + alpha-D-galactose 1-phosphate

UDP-alpha-D-galactose + undecaprenyl phosphate = UMP + alpha-D-galactosyl-diphosphoundecaprenol

UDP-galactose + H2O = UDP + D-galactose

135464

3.6.1.13

UDP-galactose + H2O = UDP + galactose

209946

3.6.1.45

UDP-galactose = UMP + galactose 1-phosphate

209944

3.6.1.9

UDP-alpha-D-galactose + H2O = UMP + alpha-D-galactose-1-phosphate

246823, 246827, 208391, 246806

5.1.3.16

UDP-galactose = UDP-glucose

UDP-alpha-D-galactose = UDP-alpha-D-glucose

746915

5.4.99.9

36 entries

Product in Enzyme-catalyzed Reactions (62 results)

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2.4.1.234

UDP + kaempferol 3-O-beta-D-galactoside = UDP-alpha-D-galactose + kaempferol

2.7.7.10

UTP + alpha-D-galactose 1-phosphate = diphosphate + UDP-galactose

642821, 642816, 642813, 637084, 642819, 642817, 642818, -

UTP + alpha-D-galactose 1-phosphate = diphosphate + UDP-alpha-D-galactose

Activator in Enzyme-catalyzed Reactions (1 result)

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4.1.1.35

0.2 mM, activates to 117% of control

663764

Inhibitor in Enzyme-catalyzed Reactions (35 results)

2 mM, less than 15% inhibition

42% inhibition

inhibition or chenodeoxycholic acid and testosterone glucuronidation

competitive

much lower affinity for OGT compared with UDP-GlcNAc

above 0.2 mM

weak

competitive inhibition, Ki: 29 mM

246827

4.2.1.135

51% inhibition of the recombinant enzyme at 0.2 mM

3D Structure of Enzyme-Ligand-Complex (PDB) (512 results)

Enzyme Kinetic Parameters

k_cat Value (Turnover Number) (165 results)

26.19

with quercetin as cosubstrate, at pH 7.5 and 30°C

0.000333

0.05

using fusion construct CgtBOH4384DELTA30-MalE (mutant with deletion of 30 amino acids from carboxy terminus + C-terminal MalE fusion)

K_M Value (365 results)

0.4

1.05

pH 6, 37°C, + pyridine 3-O-beta-galactoside

2.7

0.2

0.5

0.36

0.25

1.2

pH 7.0, 37°C

722340

2.4.1.304

0.25

pH 7, 37°C

0.02619

with quercetin as cosubstrate, at pH 7.5 and 30°C

0.074

0.006

0.01

0.00055

in 50 mM Tris-HCl (pH 8.5), 25 mM MgCl2, 1% (w/v) CHAPS, at 37°C

0.05

K_i Value (5 results)

80°C, pH 5.0

competitive inhibition

246827

IC₅₀ Value (1 result)

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2.4.1.255

0.013

much lower affinity for OGT compared with UDP-GlcNAc

705266

References & Links

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Show Reference (755 entries)

Links to other databases for UDP-alpha-D-galactose

Ligand UDP-alpha-D-galactose

Basic Ligand Information

Related pathways

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (241 results)

In Vivo Product in Enzyme-catalyzed Reactions (25 results)

Substrate in Enzyme-catalyzed Reactions (1698 results)

Product in Enzyme-catalyzed Reactions (62 results)

Activator in Enzyme-catalyzed Reactions (1 result)

Inhibitor in Enzyme-catalyzed Reactions (35 results)

3D Structure of Enzyme-Ligand-Complex (PDB) (512 results)

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (165 results)

KM Value (365 results)

Ki Value (5 results)

IC50 Value (1 result)

References & Links

Literature References (755)

Links to other databases for UDP-alpha-D-galactose

k_cat Value (Turnover Number) (165 results)

K_M Value (365 results)

K_i Value (5 results)

IC₅₀ Value (1 result)