| 词条 | Uridine monophosphate |
| 释义 |
| Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 446304818 | ImageFile =Uridinmonophosphat protoniert.svg | ImageAlt = Skeletal formula of UMP | ImageFile1 = Uridine monophosphate anion 3D ball.png | ImageAlt1 = Ball-and-stick model of the UMP molecule as an anion | IUPACName =[(2R,3S,4R,5R)-5-(2,4-Dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl dihydrogen phosphate | OtherNames =Uridylic acid; Uridine 5'-monophosphate; 5'-Uridylic acid; Uridine 5'-phosphate; Uridine phosphate; 5'-UMP; Uridine 5'-phosphoric acid |Section1={{Chembox Identifiers | IUPHAR_ligand = 5125 | CASNo =58-97-9 | CASNo_Ref = {{cascite|correct|CAS}} | PubChem = 6030 | ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} | ChemSpiderID = 5808 | SMILES = c1cn(c(=O)[nH]c1=O)[C@H]2[C@@H]([C@@H]([C@H](O2)COP(=O)(O)O)O)O | InChI = 1/C9H13N2O9P/c12-5-1-2-11(9(15)10-5)8-7(14)6(13)4(20-8)3-19-21(16,17)18/h1-2,4,6-8,13-14H,3H2,(H,10,12,15)(H2,16,17,18)/t4-,6-,7-,8-/m1/s1 | InChIKey = DJJCXFVJDGTHFX-XVFCMESIBD | StdInChI_Ref = {{stdinchicite|changed|chemspider}} | StdInChI = 1S/C9H13N2O9P/c12-5-1-2-11(9(15)10-5)8-7(14)6(13)4(20-8)3-19-21(16,17)18/h1-2,4,6-8,13-14H,3H2,(H,10,12,15)(H2,16,17,18)/t4-,6-,7-,8-/m1/s1 | StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} | StdInChIKey = DJJCXFVJDGTHFX-XVFCMESISA-N | MeSHName =Uridine+monophosphate |Section2={{Chembox Properties | C=9 | H=13 | N=2 | O=9 | P=1 | Appearance = | pKa = 1.0, 6.4, 9.5 | Density = | MeltingPtC = 202 | MeltingPt_notes = (decomposes)[1] | BoilingPt = | Solubility = good, also in methanol [1] |Section3={{Chembox Hazards | MainHazards = | FlashPt = | AutoignitionPt = }}Uridine monophosphate (UMP), also known as 5′-uridylic acid (conjugate base uridylate), is a nucleotide that is used as a monomer in RNA. It is an ester of phosphoric acid with the nucleoside uridine. UMP consists of the phosphate group, the pentose sugar ribose, and the nucleobase uracil; hence, it is a ribonucleotide monophosphate. As a substituent or radical its name takes the form of the prefix uridylyl-. The deoxy form is abbreviated dUMP. Covalent attachment of UMP (e.g. to a protein such as adenylyltransferase) is called uridylylation (or sometimes uridylation).[2] BiosynthesisUridine monophosphate is formed from Orotidine 5'-monophosphate (orotidylic acid) in a decarboxylation reaction catalyzed by the enzyme orotidylate decarboxylase. Uncatalyzed, the decarboxylation reaction is extremely slow (estimated to occur on average one time per 78 million years). Adequately catalyzed, the reaction takes place once per second, an increase of 1017-fold.[3] In humans, the orotidylate decarboxylase function is carried out by the protein UMP synthase.[4] Defective UMP synthase can result in orotic aciduria, a metabolic disorder. Effects on animal intelligenceIn a study, gerbils fed a combination of uridine monophosphate, choline, and docosahexaenoic acid (DHA) were found to have significantly improved performance in running mazes over those not fed the supplements, implying an increase in cognitive function.[5] In foodsIn brain research studies, uridine monophosphate is used as a convenient delivery compound for uridine.[6] Uridine is the active component of this compound. Uridine is present in many foods, mainly in the form of RNA. Non-phosphorylated uridine is not bioavailable beyond first-pass metabolism, as it is almost entirely catabolised in the liver and gastrointestinal tract.[7] See also
References1. ^1 {{cite book | vauthors = Lide M, Lide DR | title = CRC Handbook of Chemistry and Physics | edition = 87 | pages = 3–56 | publisher = CRC Press | year = 1998 | isbn = 978-0-8493-0594-8 }} {{Nucleobases, nucleosides, and nucleotides}}{{Nucleotide metabolism intermediates}}{{Purinergics}}2. ^{{cite book | vauthors = Voet D, Voet JG, Pratt CW | year = 2008 | title = Fundamentals of Biochemistry | edition = 3rd | publisher = John Wiley & Sons }} 3. ^{{cite book | vauthors = Berg J, Tymoczko JL, Stryer L | title = Biochemistry | publisher = W. H. Freeman | edition = 6th | location = San Francisco | year = 2006 | isbn = 0-7167-8724-5 }} 4. ^{{cite journal | vauthors = Winkler JK, Suttle DP | title = Analysis of UMP synthase gene and mRNA structure in hereditary orotic aciduria fibroblasts | journal = American Journal of Human Genetics | volume = 43 | issue = 1 | pages = 86–94 | date = July 1988 | pmid = 2837086 | pmc = 1715274 }} 5. ^{{cite journal | vauthors = Holguin S, Martinez J, Chow C, Wurtman R | title = Dietary uridine enhances the improvement in learning and memory produced by administering DHA to gerbils | journal = FASEB Journal : Official Publication of the Federation of American Societies for Experimental Biology | volume = 22 | issue = 11 | pages = 3938–46 | date = November 2008 | pmid = 18606862 | pmc = 2574024 | doi = 10.1096/fj.08-112425 | laysummary = https://www.sciencedaily.com/releases/2008/07/080702150706.htm | laysource = ScienceDaily }} 6. ^{{cite journal | vauthors = Wurtman RJ, Cansev M, Sakamoto T, Ulus IH | title = Use of phosphatide precursors to promote synaptogenesis | journal = Annual Review of Nutrition | volume = 29 | pages = 59–87 | date = 2009 | pmid = 19400698 | doi = 10.1146/annurev-nutr-080508-141059 }} 7. ^{{cite journal | vauthors = Gasser T, Moyer JD, Handschumacher RE | title = Novel single-pass exchange of circulating uridine in rat liver | journal = Science | volume = 213 | issue = 4509 | pages = 777–8 | date = August 1981 | pmid = 7256279 | doi = 10.1126/science.7256279 }} 2 : Nucleotides|Pyrimidinediones |
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