UDP-Glucose (ECMDB04171) (M2MDB000651)
Record Information | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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Version | 2.0 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Creation Date | 2012-05-31 14:07:18 -0600 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Update Date | 2015-09-13 12:56:14 -0600 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Secondary Accession Numbers |
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Identification | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Name: | UDP-Glucose | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Description | UDP-glucose is key intermediate in carbohydrate metabolism. Serves as a precursor of glycogen, can be metabolized into UDPgalactose and UDPglucuronic acid which can then be incorporated into polysaccharides as galactose and glucuronic acid. Also serves as a precursor of lipopolysaccharides. | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Structure | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Synonyms: |
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Chemical Formula: | C15H24N2O17P2 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Weight: | Average: 566.3018 Monoisotopic: 566.055020376 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
InChI Key: | HSCJRCZFDFQWRP-LPTOLDDLSA-N | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
InChI: | InChI=1S/C15H24N2O17P2/c18-3-5-8(20)10(22)12(24)14(32-5)33-36(28,29)34-35(26,27)30-4-6-9(21)11(23)13(31-6)17-2-1-7(19)16-15(17)25/h1-2,5-6,8-14,18,20-24H,3-4H2,(H,26,27)(H,28,29)(H,16,19,25)/t5-,6-,8-,9-,10+,11-,12-,13-,14?/m0/s1 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
CAS number: | 133-89-1 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
IUPAC Name: | [({[(2R,3S,4R,5R)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})phosphinic acid | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Traditional IUPAC Name: | udp-α-D-glucose | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
SMILES: | OC[C@@H]1OC(OP(O)(=O)OP(O)(=O)OC[C@@H]2O[C@@H]([C@@H](O)[C@H]2O)N2C=CC(=O)NC2=O)[C@@H](O)[C@H](O)[C@H]1O | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Chemical Taxonomy | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Description | belongs to the class of organic compounds known as pyrimidine nucleotide sugars. These are pyrimidine nucleotides bound to a saccharide derivative through the terminal phosphate group. | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Kingdom | Organic compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Super Class | Nucleosides, nucleotides, and analogues | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Class | Pyrimidine nucleotides | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Sub Class | Pyrimidine nucleotide sugars | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Direct Parent | Pyrimidine nucleotide sugars | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Alternative Parents |
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Substituents |
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Molecular Framework | Aromatic heteromonocyclic compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
External Descriptors |
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Physical Properties | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
State: | Solid | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Charge: | -2 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Melting point: | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Experimental Properties: |
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Predicted Properties |
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Biological Properties | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Cellular Locations: | Cytoplasm | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Reactions: | Water + UDP-Glucose > Glucose 1-phosphate +2 Hydrogen ion + Uridine 5'-monophosphate Galactose 1-phosphate + UDP-Glucose <> Glucose 1-phosphate + Uridine diphosphategalactose UDP-Glucose <> Uridine diphosphategalactose Glucose 1-phosphate + Hydrogen ion + Uridine triphosphate <> Pyrophosphate + UDP-Glucose Glucose 6-phosphate + UDP-Glucose > Hydrogen ion + Trehalose 6-phosphate + Uridine 5'-diphosphate Water + 2 NAD + UDP-Glucose <>3 Hydrogen ion +2 NADH + Uridine diphosphate glucuronic acid + UDP-Glucuronic acid O-Acetyl-rhamanosyl-N-acetylglucosamyl-undecaprenyl diphosphate + UDP-Glucose > Glucosyl-O-acetyl-rhamanosyl-N-acetylglucosamyl-undecaprenyl diphosphate + Hydrogen ion + Uridine 5'-diphosphate glucosyl-galactosyl-glucosyl-inner core oligosaccharide lipid A + UDP-Glucose > glucosyl-glucosyl-galactosyl-glucosyl-inner core oligosaccharide lipid A + Hydrogen ion + Uridine 5'-diphosphate galactosyl-glucosyl-inner core oligosaccharide lipid A + UDP-Glucose > glucosyl-galactosyl-glucosyl-inner core oligosaccharide lipid A + Hydrogen ion + Uridine 5'-diphosphate glucosyl-inner core oligosaccharide lipid A + UDP-Glucose > galactosyl-glucosyl-inner core oligosaccharide lipid A + Hydrogen ion + Uridine 5'-diphosphate inner core oligosaccharide lipid A (E coli) + UDP-Glucose > glucosyl-inner core oligosaccharide lipid A + Hydrogen ion + Uridine 5'-diphosphate UDP-Glucose + Water + 2 NAD <> Uridine diphosphate glucuronic acid +2 NADH +2 Hydrogen ion UDP-Glucose + Water <> Uridine 5'-monophosphate + Glucose 1-phosphate Uridine triphosphate + Glucose 1-phosphate <> Pyrophosphate + UDP-Glucose UDP-Glucose + LPS (1-O-antigen) <> Uridine 5'-diphosphate + D-Glucosyllipopolysaccharide UDP-Glucose + Glucose 6-phosphate <> Uridine 5'-diphosphate + Trehalose 6-phosphate UDP-Glucose + Cellulose <> Uridine 5'-diphosphate + Cellulose GDP-L-Fucose + UDP-Glucose + Uridine diphosphate glucuronic acid + Uridine diphosphategalactose colanic acid UDP-Glucose + a lipopolysaccharide D-glucosyl-lipopolysaccharide + Uridine 5'-diphosphate Hydrogen ion + Glucose 1-phosphate + Uridine triphosphate > UDP-Glucose + Pyrophosphate UDP-Glucose + Heptosyl2-KDO2-lipid A > Hydrogen ion + Glucosyl-heptosyl2-KDO2-lipid A + Uridine 5'-diphosphate UDP-Glucose + Galactosyl-glucosyl-heptosyl3-KDO2-lipid A-bisphosphate > Hydrogen ion + Galactosyl-glucosyl2-heptosyl3-KDO2-lipid A-bisphosphate + Uridine 5'-diphosphate UDP-Glucose + Galactosyl-glucosyl2-heptosyl3-KDO2-lipid A-bisphosphate > Hydrogen ion + Galactosyl-glucosyl3-heptosyl3-KDO2-lipid A-bisphosphate + Uridine 5'-diphosphate UDP-Glucose + α-D-glucose 6-phosphate > Hydrogen ion + Uridine 5'-diphosphate + Trehalose 6-phosphate UDP-Glucose + Water + NAD > Hydrogen ion + NADH + Uridine diphosphate glucuronic acid UDP-Glucose + (1,4-beta-D-glucosyl)(n) > Uridine 5'-diphosphate + (1,4-beta-D-glucosyl)(n+1) More...UDP-Glucose + Galactose 1-phosphate > Alpha-D-glucose 1-phosphate + Uridine diphosphategalactose UDP-Glucose > Uridine diphosphategalactose Uridine triphosphate + Alpha-D-glucose 1-phosphate > Pyrophosphate + UDP-Glucose UDP-Glucose + Glucose 6-phosphate > Uridine 5'-diphosphate + Trehalose 6-phosphate UDP-Glucose + LPS (1-O-antigen) > Uridine 5'-diphosphate + D-glucosyl-lipopolysaccharide UDP-Glucose + 2 NAD + Water > UDP-Glucuronic acid +2 NADH UDP-Glucose <> Uridine 5'-diphosphate UDP-Glucose + Di-trans,poly-cis-undecaprenyl phosphate <> Uridine 5'-monophosphate + alpha-D-Glucopyranosyl-diphospho-ditrans,octacis-undecaprenol Glucose 1-phosphate + Uridine triphosphate + Hydrogen ion + Uridine triphosphate > Pyrophosphate + UDP-Glucose β-D-glucose 1-phosphate + Uridine triphosphate + Hydrogen ion + Uridine triphosphate > UDP-Glucose + Pyrophosphate Alpha-D-glucose 1-phosphate + Uridine triphosphate + Hydrogen ion + Uridine triphosphate > Pyrophosphate + UDP-Glucose UDP-Glucose > Uridine diphosphategalactose + Uridine diphosphategalactose Galactose 1-phosphate + UDP-Glucose + Galactose 1-phosphate > Uridine diphosphategalactose + Glucose 1-phosphate + Uridine diphosphategalactose Alpha-D-glucose 1-phosphate + UDP-galactose > UDP-Glucose + Galactose 1-phosphate + Galactose 1-phosphate UDP-Glucose <> Uridine diphosphategalactose + Uridine diphosphategalactose (heptosyl)2-Kdo2-lipid A + UDP-Glucose > Uridine 5'-diphosphate + Hydrogen ion + glucosyl-(heptosyl)2-Kdo2-lipid A galactosyl-glucosyl-(heptosyl)3-Kdo2-lipid A-bisphosphate + UDP-Glucose > Uridine 5'-diphosphate + Hydrogen ion + galactosyl-(glucosyl)2-(heptosyl)3-Kdo2-lipid A-bisphosphate galactosyl-(glucosyl)2-(heptosyl)3-Kdo2-lipid A-bisphosphate + UDP-Glucose > Uridine 5'-diphosphate + Hydrogen ion + galactosyl-(glucosyl)3-(heptosyl)3-Kdo2-lipid A-bisphosphate UDP-Glucose + 2 NAD + Water > UDP-Glucuronic acid +2 NADH +3 Hydrogen ion UDP-Glucose + Alpha-D-glucose 6-phosphate > Uridine 5'-diphosphate + Trehalose 6-phosphate + Hydrogen ion + Uridine 5'-diphosphate UDP-Glucose + D-Fructose + D-Fructose <> Sucrose + Phosphate UDP-Glucose + Mannose 6-phosphate > alpha,alpha-Trehalose 6-phosphate + Uridine 5'-diphosphate + Hydrogen ion UDP-Glucose <> Uridine diphosphategalactose Glucose 1-phosphate + Hydrogen ion + Uridine triphosphate <> Pyrophosphate + UDP-Glucose Uridine triphosphate + Glucose 1-phosphate <> Pyrophosphate + UDP-Glucose UDP-Glucose <> Uridine diphosphategalactose | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
SMPDB Pathways: |
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KEGG Pathways: |
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EcoCyc Pathways: |
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Concentrations | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Find out more about how we convert literature concentrations. | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Spectra | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Spectra: | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
References | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
References: |
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Synthesis Reference: | Burma, D. P.; Mortimer, D. C. Biosynthesis of uridine diphosphate glucose and sucrose in sugar-beet leaf. Archives of Biochemistry and Biophysics (1956), 62 16-28. | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Material Safety Data Sheet (MSDS) | Download (PDF) | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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External Links: |
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Enzymes
- General function:
- Involved in hydrolase activity
- Specific function:
- Degradation of external UDP-glucose to uridine monophosphate and glucose-1-phosphate, which can then be used by the cell
- Gene Name:
- ushA
- Uniprot ID:
- P07024
- Molecular weight:
- 60824
Reactions
UDP-sugar + H(2)O = UMP + alpha-D-aldose 1-phosphate. |
A 5'-ribonucleotide + H(2)O = a ribonucleoside + phosphate. |
- General function:
- Involved in catalytic activity
- Specific function:
- UDP-glucose = UDP-galactose
- Gene Name:
- galE
- Uniprot ID:
- P09147
- Molecular weight:
- 37265
Reactions
UDP-glucose = UDP-galactose. |
- General function:
- Involved in UDP-glucose:hexose-1-phosphate uridylyltransferase activity
- Specific function:
- UDP-glucose + alpha-D-galactose 1-phosphate = alpha-D-glucose 1-phosphate + UDP-galactose
- Gene Name:
- galT
- Uniprot ID:
- P09148
- Molecular weight:
- 39645
Reactions
UDP-glucose + alpha-D-galactose 1-phosphate = alpha-D-glucose 1-phosphate + UDP-galactose. |
- General function:
- Involved in enzyme regulator activity
- Specific function:
- UTP + alpha-D-glucose 1-phosphate = diphosphate + UDP-glucose
- Gene Name:
- galF
- Uniprot ID:
- P0AAB6
- Molecular weight:
- 32829
Reactions
UTP + alpha-D-glucose 1-phosphate = diphosphate + UDP-glucose. |
- General function:
- Involved in UTP:glucose-1-phosphate uridylyltransferase activity
- Specific function:
- May play a role in stationary phase survival
- Gene Name:
- galU
- Uniprot ID:
- P0AEP3
- Molecular weight:
- 32942
Reactions
UTP + alpha-D-glucose 1-phosphate = diphosphate + UDP-glucose. |
- General function:
- Involved in nucleoside-triphosphate diphosphatase activity
- Specific function:
- Specific function unknown
- Gene Name:
- mazG
- Uniprot ID:
- P0AEY3
- Molecular weight:
- 30412
Reactions
ATP + H(2)O = AMP + diphosphate. |
- General function:
- Involved in transferase activity, transferring glycosyl groups
- Specific function:
- UDP-glucose + lipopolysaccharide = UDP + D- glucosyl-lipopolysaccharide
- Gene Name:
- rfaJ
- Uniprot ID:
- P27129
- Molecular weight:
- 39040
Reactions
UDP-glucose + lipopolysaccharide = UDP + D-glucosyl-lipopolysaccharide. |
- General function:
- Involved in catalytic activity
- Specific function:
- Catalyzes the transfer of glucose from UDP-glucose to glucose-6-phosphate to form alpha,alpha-1,1 trehalose-6-phosphate. Acts with retention of the anomeric configuration of the UDP-sugar donor. Essential for viability of the cells at low temperatures and at elevated osmotic strength
- Gene Name:
- otsA
- Uniprot ID:
- P31677
- Molecular weight:
- 53611
Reactions
UDP-glucose + D-glucose 6-phosphate = UDP + alpha,alpha-trehalose 6-phosphate. |
- General function:
- Involved in cellulose synthase activity
- Specific function:
- Catalytic subunit of cellulose synthase. It polymerizes uridine 5'-diphosphate glucose to cellulose, which is produced as an extracellular component for mechanical and chemical protection at the onset of the stationary phase, when the cells exhibit multicellular behavior (rdar morphotype). Coexpression of cellulose and thin aggregative fimbriae leads to a hydrophobic network with tightly packed cells embedded in a highly inert matrix
- Gene Name:
- bcsA
- Uniprot ID:
- P37653
- Molecular weight:
- 99784
Reactions
UDP-glucose + (1,4-beta-D-glucosyl)(n) = UDP + (1,4-beta-D-glucosyl)(n+1). |
- General function:
- Involved in catalytic activity
- Specific function:
- Sucrose + phosphate = D-fructose + alpha-D- glucose 1-phosphate
- Gene Name:
- ycjM
- Uniprot ID:
- P76041
- Molecular weight:
- 64185
Reactions
Sucrose + phosphate = D-fructose + alpha-D-glucose 1-phosphate. |
- General function:
- Involved in oxidation-reduction process
- Specific function:
- UDP-glucose + 2 NAD(+) + H(2)O = UDP- glucuronate + 2 NADH
- Gene Name:
- ugd
- Uniprot ID:
- P76373
- Molecular weight:
- 43656
Reactions
UDP-glucose + 2 NAD(+) + H(2)O = UDP-glucuronate + 2 NADH. |
- General function:
- Involved in biosynthetic process
- Specific function:
- Involved in the addition of the first glucose residue to the lipopolysaccharide core
- Gene Name:
- rfaG
- Uniprot ID:
- P25740
- Molecular weight:
- 42284
- General function:
- Involved in biosynthetic process
- Specific function:
- Adds a galactose goup to a glucose group of LPS
- Gene Name:
- rfaB
- Uniprot ID:
- P27127
- Molecular weight:
- 40826
- General function:
- Involved in biosynthetic process
- Specific function:
- May be a glycosyltransferase involved in the transfer of UDP-GalF and UDP-glucose
- Gene Name:
- yefI
- Uniprot ID:
- P37751
- Molecular weight:
- 43188
- General function:
- Involved in transferase activity, transferring glycosyl groups
- Specific function:
- UDP-galactose + lipopolysaccharide = UDP + 3- alpha-D-galactosyl-[lipopolysaccharide glucose]
- Gene Name:
- rfaI
- Uniprot ID:
- P27128
- Molecular weight:
- 39423
Reactions
UDP-galactose + lipopolysaccharide = UDP + 3-alpha-D-galactosyl-[lipopolysaccharide glucose]. |
Transporters
- General function:
- Involved in transporter activity
- Specific function:
- Non-specific porin
- Gene Name:
- ompN
- Uniprot ID:
- P77747
- Molecular weight:
- 41220
- General function:
- Involved in transporter activity
- Specific function:
- Uptake of inorganic phosphate, phosphorylated compounds, and some other negatively charged solutes
- Gene Name:
- phoE
- Uniprot ID:
- P02932
- Molecular weight:
- 38922
- General function:
- Involved in transporter activity
- Specific function:
- OmpF is a porin that forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane. It is also a receptor for the bacteriophage T2
- Gene Name:
- ompF
- Uniprot ID:
- P02931
- Molecular weight:
- 39333
- General function:
- Involved in transporter activity
- Specific function:
- Forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane
- Gene Name:
- ompC
- Uniprot ID:
- P06996
- Molecular weight:
- 40368