| Revision as of 12:57, 15 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 472799192 of page Uridine_diphosphate_galactose for the Chem/Drugbox validation project (updated: 'ChEMBL', 'CASNo'). |
Latest revision as of 05:27, 16 December 2024 edit OAbot (talk | contribs)Bots440,440 editsm Open access bot: pmc updated in citation with #oabot. |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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{{chembox |
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{{chembox |
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| verifiedrevid = 470620352 |
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| verifiedrevid = 476997454 |
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|ImageFile=UDP-Galactose.svg |
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| ImageFile=UDP-Galactose.svg |
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|IUPACName= |
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| IUPACName=Uridine 5′-(α-<small>D</small>-galactopyranosyl dihydrogen diphosphate) |
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| SystematicName=''O''<sup>1</sup>-<nowiki/>{methyl} ''O''<sup>3</sup>- dihydrogen diphosphate |
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|Section1= {{Chembox Identifiers |
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| InChI = 1/C9H12N2O6.C6H14O12P2/c12-3-4-6(14)7(15)8(17-4)11-2-1-5(13)10-9(11)16;7-1-3(9)5(10)6(18-20(14,15)16)4(2-8)17-19(11,12)13/h1-2,4,6-8,12,14-15H,3H2,(H,10,13,16);2-7,9-10H,1H2,(H2,11,12,13)(H2,14,15,16)/p-4/t4-,6-,7-,8-;3-,4+,5+,6-/m11/s1 |
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|Section1={{Chembox Identifiers |
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| InChI = 1/C9H12N2O6.C6H14O12P2/c12-3-4-6(14)7(15)8(17-4)11-2-1-5(13)10-9(11)16;7-1-3(9)5(10)6(18-20(14,15)16)4(2-8)17-19(11,12)13/h1-2,4,6-8,12,14-15H,3H2,(H,10,13,16);2-7,9-10H,1H2,(H2,11,12,13)(H2,14,15,16)/p-4/t4-,6-,7-,8-;3-,4+,5+,6-/m11/s1 |
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| InChIKey = UYLAOKYVSPTOGT-HUYLZDLQBS |
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| InChIKey = UYLAOKYVSPTOGT-HUYLZDLQBS |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = UYLAOKYVSPTOGT-UESRDHDISA-J |
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| StdInChIKey = UYLAOKYVSPTOGT-UESRDHDISA-J |
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| CASNo_Ref = {{cascite|changed|??}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = <!-- blanked - oldvalue: 2956-16-3 --> |
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| CASNo=2956-16-3 |
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| PubChem=1166 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = O2HY4WY2W1 |
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| PubChem=1166 |
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| ChEMBL_Ref = {{ebicite|changed|EBI}} |
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| ChEMBL_Ref = {{ebicite|changed|EBI}} |
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| ChEMBL = <!-- blanked - oldvalue: 1743884 --> |
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| ChEMBL = 1743884 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID=19951534 |
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| ChemSpiderID=19951534 |
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| SMILES = OC(O)(O)(OP()()=O)(C=O)OP()()=O.O=C\1NC(=O)N(/C=C/1)2O(CO)(O)2O |
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| SMILES = OC()()1()O()(O(=O)(O)O(=O)(O)OC()()2()O()(N3C()=C()C(=O)N()C3=O)()(O)2()O)()(O)()(O)1()O |
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| MeSHName=Uridine+diphosphate+galactose |
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| MeSHName=Uridine+diphosphate+galactose |
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|Section2= {{Chembox Properties |
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|Section2={{Chembox Properties |
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| Formula=C<sub>15</sub>H<sub>24</sub>N<sub>2</sub>O<sub>17</sub>P<sub>2</sub> |
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| Formula=C<sub>15</sub>H<sub>24</sub>N<sub>2</sub>O<sub>17</sub>P<sub>2</sub> |
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| MolarMass=566.302 g/mol |
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| MolarMass=566.302 g/mol |
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|Section3= {{Chembox Hazards |
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'''Uridine diphosphate galactose''' (''']-]''') is an intermediate in the production of ]s.<ref>{{Cite book|chapter-url=https://www.ncbi.nlm.nih.gov/books/NBK441957/|title = StatPearls|chapter = Galactose 1 Phosphate Uridyltransferase Deficiency|year = 2022|publisher = StatPearls| pmid=28722986 | last1=Los | first1=E. | last2=Ford | first2=G. A. }}</ref> It is important in ], and is the substrate for the transferase ]. |
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== Sugar metabolism == |
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Uridine diphosphate (UDP)-galactose is relevant in glycolysis. UDP-galactose is the activated form of Gal, a crucial monosaccharide building block for human milk oligosaccharide (HMO).<ref>{{cite journal | author = Mahour, R., Lee, J. W., Grimpe, P., Boecker, S., Grote, V., Klamt, S., Seidel‐Morgenstern, A., Rexer, T. F. T., & Reichl, U. | date = 2022 | title = Cell‐Free Multi‐Enzyme Synthesis and Purification of Uridine Diphosphate Galactose | journal = ChemBioChem | volume = 23 | issue = 2 | pages = e202100361-n/a | doi = 10.1002/cbic.202100361 | pmc = 9299652 }}</ref> The activated form of galactose (Gal) serves as a donor molecule involved in catalyzing the conversion of UDP-galactose to UDP-glucose. The conversion is a rate-limiting step essential to the pace of UDP-glucose production that determines the completion of glycosylation reactions.<ref>{{cite journal | author = Hou, J., Tian, S., Yang, L., Zhang, Z., & Liu, Y. | date = 2021 | title = A systematic review of the Uridine diphosphate-Galactose/Glucose-4-epimerase (UGE) in plants | journal = Plant Growth Regulation | volume = 93 | issue = 3 | pages = 267–278 | doi = 10.1007/s10725-020-00686-1 }}</ref> |
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To further explain, UDP-galactose is derived from a galactose molecule which is an epimer of glucose, and via the ], it is used be used as a precursor for the metabolism of glucose into pyruvate.<ref>{{Cite book |last1=Garrett |first1=Reginald H. |title=Biochemistry |last2=Grisham |first2=Charles M. |date=2017 |publisher=Cengage Learning |isbn=978-1-305-57720-6 |edition=6th |location=Boston, MA, USA}}</ref> When lactose is hydrolyzed, D-Galactose enters the liver via the bloodstream. There, galactokinase phosphorylates it to galactose-1-phosphate using ATP. This compound then engages in a "ping-pong" reaction with UDP-glucose, catalyzed by uridylyltransferase, yielding glucose-1-phosphate and UDP-galactose. This glucose-1-phosphate feeds into glycolysis, while UDP-galactose undergoes epimerization to regenerate UDP-glucose.<ref>{{Cite book |last1=Nelson |first1=David L. |title=Lehninger principles of biochemistry |last2=Cox |first2=Michael M. |last3=Nelson |first3=David L. |date=2013 |publisher=Macmillan Higher Education |isbn=978-1-4292-3414-6 |editor-last=Lehninger |editor-first=Albert L. |edition=6th |location=Basingstoke}}</ref> |
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==See also== |
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* ] |
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* ] |
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* ] |
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==References== |
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{{Reflist|2}} |
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{{Fructose and galactose metabolic intermediates}} |
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{{Purinergics}} |
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] |
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] |