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{{Redirect2|dUMP|DUMP|other uses|Dump (disambiguation)}} |
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|ImageFile=DUMP chemical structure.png |
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| verifiedrevid = 413157820 |
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| ImageFile=DUMP chemical structure.png |
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|OtherNames=dUMP |
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|Section1= {{Chembox Identifiers |
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| ImageAlt=Skeletal formula of dUMP as an anion |
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| CASNo=964-26-1 |
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| ImageFile1=Deoxyuridine monophosphate anion 3D ball.png |
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| PubChem=688 |
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| ImageAlt1=Ball-and-stick model of the dUMP molecule as an anion |
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| IUPACName=2′-Deoxyuridylic acid |
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| MeSHName=2'-deoxyuridine-5'-monophosphate |
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| SystematicName=methyl dihydrogen phosphate |
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| OtherNames=dUMP |
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|Section1={{Chembox Identifiers |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo=964-26-1 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = N9J10KFG94 |
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| PubChem=688 |
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| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
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| ChemSpiderID = 58574 |
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| SMILES = O=P(O)(O)OC2O(N\1C(=O)NC(=O)/C=C/1)C2O |
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| InChI = 1/C9H13N2O8P/c12-5-3-8(11-2-1-7(13)10-9(11)14)19-6(5)4-18-20(15,16)17/h1-2,5-6,8,12H,3-4H2,(H,10,13,14)(H2,15,16,17)/t5-,6+,8+/m0/s1 |
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| InChIKey = JSRLJPSBLDHEIO-SHYZEUOFBW |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChI = 1S/C9H13N2O8P/c12-5-3-8(11-2-1-7(13)10-9(11)14)19-6(5)4-18-20(15,16)17/h1-2,5-6,8,12H,3-4H2,(H,10,13,14)(H2,15,16,17)/t5-,6+,8+/m0/s1 |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChIKey = JSRLJPSBLDHEIO-SHYZEUOFSA-N |
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| ChEMBL_Ref = {{ebicite|changed|EBI}} |
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| ChEMBL = 211312 |
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| MeSHName=uridine-4'-monophosphate |
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|Section2= {{Chembox Properties |
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|Section2={{Chembox Properties |
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| Formula=C<sub>9</sub>H<sub>13</sub>N<sub>2</sub>O<sub>8</sub>P |
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| Formula=C<sub>9</sub>H<sub>13</sub>N<sub>2</sub>O<sub>8</sub>P |
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| MolarMass=308.182 |
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| MolarMass=308.182 |
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'''Deoxyuridine monophosphate''' is a ]. |
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'''Deoxyuridine monophosphate''' ('''dUMP'''), also known as '''deoxyuridylic acid''' or '''deoxyuridylate''' in its ] and conjugate base forms, respectively, is a ]. |
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It is an intermediate in the metabolism of ]s. |
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It is an intermediate in the metabolism of ]s. |
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== Biosynthesis == |
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Deoxyuridine monophosphate (dUMP) is the deoxygenated form of ] (UMP), and is the precursor to deoxythymidine monophosphate (dTMP), a component of DNA ] biosynthesis.<ref>{{Cite book|title=Biochemistry|last=Berg|first=J. M.|last2=Tymoczko|first2=J. L.|last3=Stryer|first3=L.|publisher=W H Freeman|year=2002|isbn=978-1-4641-2610-9|edition=5th|location=New York}}</ref> By replacing the ] at the 2' carbon of ribose with a hydrogen, UMP becomes deoxygenated to dUMP. |
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The synthesis of deoxyuridine monophosphate (dUMP) is a multi-step process that begins with ] (UMP), the product of ] biosynthesis.<ref>{{Cite journal|last=Shambaugh|first=G. E.|date=June 1979|title=Pyrimidine biosynthesis|journal=The American Journal of Clinical Nutrition|volume=32|issue=6|pages=1290–1297|doi=10.1093/ajcn/32.6.1290|pmid=35970}}</ref> The enzyme ] converts UMP and ] to ] (UDP) and ]. |
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In the presence of excess ATP, the enzyme ] initiates a chain reaction with UDP, which catalyzes the formation of deoxyuridine diphosphate (dUDP), which is then converted to deoxyuridine triphosphate (dUTP), then deoxyuridine monophosphate (dUMP) via the addition or removal of phosphate groups.<ref name=":2">{{Cite book|title=Biochemistry|last=Garrett|first=Reginald H.|last2=Grisham|first2=Charles M.|publisher=Brooks/Cole, Cengage Learning|year=2013|isbn=9781133106296|edition=6th|location=Belmont, CA|pages=949}}</ref> |
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== Interactive pathway map == |
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{{FluoropyrimidineActivity WP1601|highlight=Deoxyuridine_monophosphate}} |
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==See also== |
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==See also== |
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* ] |
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* ] |
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* ] |
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* ] |
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== Notes == |
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{{reflist}} |
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{{Nucleobases, nucleosides, and nucleotides}} |
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{{Nucleobases, nucleosides, and nucleotides}} |
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{{biochem-stub}} |
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] |
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] |
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] |
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] |
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] |
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