Uridine diphosphate galactose
{{chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 476997454
| ImageFile=UDP-Galactose.svg
| ImageClass = skin-invert-image
| ImageSize=
| IUPACName=Uridine 5′-(α-D-galactopyranosyl dihydrogen diphosphate)
| SystematicName=O1-
| OtherNames=
|Section1={{Chembox Identifiers
| 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
| InChIKey = UYLAOKYVSPTOGT-HUYLZDLQBS
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/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
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = UYLAOKYVSPTOGT-UESRDHDISA-J
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo=2956-16-3
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = O2HY4WY2W1
| PubChem=1166
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 1743884
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID=19951534
| SMILES = [H]OC([H])([H])[C@]1([H])O[C@]([H])(O[P@@](=O)(O[H])O[P@](=O)(O[H])OC([H])([H])[C@]2([H])O[C@@]([H])(N3C([H])=C([H])C(=O)N([H])C3=O)[C@]([H])(O[H])[C@@]2([H])O[H])[C@]([H])(O[H])[C@]([H])(O[H])[C@@]1([H])O[H]
| MeSHName=Uridine+diphosphate+galactose
}}
|Section2={{Chembox Properties
| Formula=C15H24N2O17P2
| MolarMass=566.302 g/mol
| Appearance=
| Density=
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| Solubility=
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|Section3={{Chembox Hazards
| MainHazards=
| FlashPt=
| AutoignitionPt =
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Uridine diphosphate galactose (UDP-galactose) is an intermediate in the production of polysaccharides.{{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. }} It is important in nucleotide sugars metabolism, and is the substrate for the transferase B4GALT5.
Sugar metabolism
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).{{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 }} 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.{{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 }}
To further explain, UDP-galactose is derived from a galactose molecule which is an epimer of glucose, and via the Leloir pathway, it is used be used as a precursor for the metabolism of glucose into pyruvate.{{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}} 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.{{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}}
See also
References
{{Reflist|2}}
{{Fructose and galactose metabolic intermediates}}
{{Purinergics}}