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Revision as of 15:53, 20 October 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{chembox}} (changes to verified fields - updated 'DrugBank_Ref', 'UNII_Ref', 'KEGG_Ref', 'CASNo_Ref') per Chem/Drugbox validation (report errors or bugs)← Previous edit Latest revision as of 00:46, 8 May 2023 edit undoLegionMammal978 (talk | contribs)Extended confirmed users7,894 edits add semisystematic name 
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{{chembox {{chembox
⚫ | verifiedrevid = 470620377
| Verifiedfields = changed
⚫ | verifiedrevid = 442182436
| ImageFile = UDP-Glucose.svg | ImageFile = UDP-Glucose.svg
| ImageSize = 200px | ImageSize =
| IUPACName = Uridine 5′-(α-<small>D</small>-glucopyranosyl dihydrogen diphosphate)
| IUPACName = <nowiki>methoxy-hydroxyphosphoryl] hydrogen | SystematicName = ''O''<sup>1</sup>-<nowiki/>{methyl} ''O''<sup>3</sup>- dihydrogen diphosphate
phosphate
| OtherNames = UDP-glucose | OtherNames = UDP-glucose
| Section1 = {{Chembox Identifiers | Section1 = {{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 8308 | ChemSpiderID = 8308
| ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL_Ref = {{ebicite|correct|EBI}}
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| CASNo_Ref = {{cascite|correct|CAS}} | CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 133-89-1 | CASNo = 133-89-1
| UNII_Ref = {{fdacite|correct|FDA}}
⚫ | PubChem = 8629
| UNII = V50K1D7P4Y
⚫ | PubChem = 8629
| IUPHAR_ligand = 1783 | IUPHAR_ligand = 1783
| ChEBI_Ref = {{ebicite|changed|EBI}} | ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 52249 | ChEBI = 52249
| SMILES = O=P(O1O((O)(O)1O)CO)(O)OP(=O)(O)OC3O(N2/C=C\C(=O)NC2=O)(O)3O | SMILES = O=P(O1O((O)(O)1O)CO)(O)OP(=O)(O)OC3O(N2/C=C\C(=O)NC2=O)(O)3O
| MeSHName = Uridine+Diphosphate+Glucose | MeSHName = Uridine+Diphosphate+Glucose
}} }}
| Section2 = {{Chembox Properties | Section2 = {{Chembox Properties
| Formula = C<sub>15</sub>H<sub>24</sub>N<sub>2</sub>O<sub>17</sub>P<sub>2</sub> | Formula = C<sub>15</sub>H<sub>24</sub>N<sub>2</sub>O<sub>17</sub>P<sub>2</sub>
| MolarMass = 566.302 g/mol | MolarMass = 566.302 g/mol
| Appearance = | Appearance =
| Density = | Density =
| MeltingPt = | MeltingPt =
| BoilingPt = | BoilingPt =
}} }}
| Section3 = {{Chembox Hazards | Section3 = {{Chembox Hazards
| Solubility = | MainHazards =
| MainHazards = | FlashPt =
| FlashPt = | AutoignitionPt =
| Autoignition =
}} }}
}} }}
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==Functions== ==Functions==
It is used in ] as an activated form of glucose as a substrate for enzymes called ]s.<ref>{{cite journal |author=Rademacher T, Parekh R, Dwek R |title=Glycobiology |journal=Annu Rev Biochem |volume=57 |issue= |pages=785–838 |year=1988 |pmid=3052290 |doi=10.1146/annurev.bi.57.070188.004033}}</ref> UDP-glucose is used in ] as an activated form of glucose, a substrate for enzymes called ]s.<ref>{{cite journal |vauthors=Rademacher T, Parekh R, Dwek R |title=Glycobiology |journal=Annu Rev Biochem |volume=57 |pages=785–838 |year=1988 |pmid=3052290 |doi=10.1146/annurev.bi.57.070188.004033}}</ref>


It is a precursor of ] and can be converted into ] and ], which can then be used as substrates by the enzymes that make ]s containing ] and ]. UDP-glucose is a precursor of ] and can be converted into ] and ], which can then be used as substrates by the enzymes that make ]s containing ] and ].


UDP-glucose can also be used as a precursor of sucrose ]s, and ]s. UDP-glucose can also be used as a precursor of sucrose, ]s and ]s.


==Components== ==Components==
UDP-glucose consists of the ] ], the ] ] ], ], and the ] ]. UDP-glucose consists of the ] group, ], ], and ].

⚫ ==References==
⚫ {{reflist}}


== See also == == See also ==
* ]
* ] * ]
* ] * ]
* ] * ]
* ] * ]
* ] * ]
* ] * ]
* ] * ]
⚫ ==References==
* ]
⚫ {{reflist}}


{{Nucleotide sugars}} {{Nucleotide sugars}}
{{Fructose and galactose metabolic intermediates}} {{Fructose and galactose metabolic intermediates}}
{{Purinergics}}


] ]
] ]

]
]
]

Latest revision as of 00:46, 8 May 2023

Uridine diphosphate glucose
Names
IUPAC name Uridine 5′-(α-D-glucopyranosyl dihydrogen diphosphate)
Systematic IUPAC name O-{methyl} O- dihydrogen diphosphate
Other names UDP-glucose
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.004.657 Edit this at Wikidata
IUPHAR/BPS
MeSH Uridine+Diphosphate+Glucose
PubChem CID
UNII
CompTox Dashboard (EPA)
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-/m1/s1Key: HSCJRCZFDFQWRP-JZMIEXBBSA-N
  • InChI=1/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-/m1/s1Key: HSCJRCZFDFQWRP-JZMIEXBBBU
SMILES
  • O=P(O1O((O)(O)1O)CO)(O)OP(=O)(O)OC3O(N2/C=C\C(=O)NC2=O)(O)3O
Properties
Chemical formula C15H24N2O17P2
Molar mass 566.302 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

Uridine diphosphate glucose (uracil-diphosphate glucose, UDP-glucose) is a nucleotide sugar. It is involved in glycosyltransferase reactions in metabolism.

Functions

UDP-glucose is used in nucleotide sugar metabolism as an activated form of glucose, a substrate for enzymes called glucosyltransferases.

UDP-glucose is a precursor of glycogen and can be converted into UDP-galactose and UDP-glucuronic acid, which can then be used as substrates by the enzymes that make polysaccharides containing galactose and glucuronic acid.

UDP-glucose can also be used as a precursor of sucrose, lipopolysaccharides and glycosphingolipids.

Components

UDP-glucose consists of the pyrophosphate group, ribose, glucose, and uracil.

See also

References

  1. Rademacher T, Parekh R, Dwek R (1988). "Glycobiology". Annu Rev Biochem. 57: 785–838. doi:10.1146/annurev.bi.57.070188.004033. PMID 3052290.
Types of nucleotide sugars
Fructose and galactose metabolic intermediates
Fructose
Galactose
Mannose
Purine receptor modulators
Receptor
(ligands)
P0 (adenine)
P1
(adenosine)
P2
(nucleotide)
P2X
(ATPTooltip Adenosine triphosphate)
P2Y
Transporter
(blockers)
CNTsTooltip Concentrative nucleoside transporters
ENTsTooltip Equilibrative nucleoside transporters
PMATTooltip Plasma membrane monoamine transporter
Enzyme
(inhibitors)
XOTooltip Xanthine oxidase
Others
Others
See also: Receptor/signaling modulators
Categories: