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Uridine monophosphate

January 01, 1970

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]

Uridine monophosphate
Names
IUPAC name
[(2R,3S,4R,5R)-5-(2,4-Dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl dihydrogen phosphate
Other names
Uridylic acid; Uridine 5'-monophosphate; 5'-Uridylic acid; Uridine 5'-phosphate; Uridine phosphate; 5'-UMP; Uridine 5'-phosphoric acid
Identifiers
  • 58-97-9 Y
3D model (JSmol)
  • Interactive image
ChemSpider
  • 5808 N
ECHA InfoCard 100.000.371
  • 5125
MeSH Uridine+monophosphate
  • 6030
UNII
  • E2OU15WN0N Y
  • DTXSID20883211
  • InChI=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 N
    Key: DJJCXFVJDGTHFX-XVFCMESISA-N N
  • 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
    Key: DJJCXFVJDGTHFX-XVFCMESIBD
  • c1cn(c(=O)[nH]c1=O)[C@H]2[C@@H]([C@@H]([C@H](O2)COP(=O)(O)O)O)O
Properties
C9H13N2O9P
Molar mass 324.182 g·mol−1
Melting point 202 °C (396 °F; 475 K) (decomposes)[1]
good, also in methanol [1]
Acidity (pKa) 1.0, 6.4, 9.5
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)

Biosynthesis edit

Uridine 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 intelligence edit

In 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 foods edit

In 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 edit

References edit

  1. ^ a b Lide M, Lide DR (1998). CRC Handbook of Chemistry and Physics (87 ed.). CRC Press. pp. 3–56. ISBN 978-0-8493-0594-8.
  2. ^ Voet D, Voet JG, Pratt CW (2008). Fundamentals of Biochemistry (3rd ed.). John Wiley & Sons.
  3. ^ Berg J, Tymoczko JL, Stryer L (2006). Biochemistry (6th ed.). San Francisco: W. H. Freeman. ISBN 0-7167-8724-5.
  4. ^ Winkler JK, Suttle DP (July 1988). "Analysis of UMP synthase gene and mRNA structure in hereditary orotic aciduria fibroblasts". American Journal of Human Genetics. 43 (1): 86–94. PMC 1715274. PMID 2837086.
  5. ^ Holguin S, Martinez J, Chow C, Wurtman R (November 2008). "Dietary uridine enhances the improvement in learning and memory produced by administering DHA to gerbils". FASEB Journal. 22 (11): 3938–46. doi:10.1096/fj.08-112425. PMC 2574024. PMID 18606862.
    • "Get Smart About What You Eat And You Might Actually Improve Your Intelligence". ScienceDaily (Press release). July 3, 2008.
  6. ^ Wurtman RJ, Cansev M, Sakamoto T, Ulus IH (2009). "Use of phosphatide precursors to promote synaptogenesis". Annual Review of Nutrition. 29: 59–87. doi:10.1146/annurev-nutr-080508-141059. PMID 19400698.
  7. ^ Gasser T, Moyer JD, Handschumacher RE (August 1981). "Novel single-pass exchange of circulating uridine in rat liver". Science. 213 (4509): 777–8. Bibcode:1981Sci...213..777G. doi:10.1126/science.7256279. PMID 7256279.

January 01, 1970
uridine, monophosphate, also, known, uridylic, acid, conjugate, base, uridylate, nucleotide, that, used, monomer, ester, phosphoric, acid, with, nucleoside, uridine, consists, phosphate, group, pentose, sugar, ribose, nucleobase, uracil, hence, ribonucleotide,. 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 Uridine monophosphate Names IUPAC name 2R 3S 4R 5R 5 2 4 Dioxopyrimidin 1 yl 3 4 dihydroxyoxolan 2 yl methyl dihydrogen phosphate Other names Uridylic acid Uridine 5 monophosphate 5 Uridylic acid Uridine 5 phosphate Uridine phosphate 5 UMP Uridine 5 phosphoric acid Identifiers CAS Number 58 97 9 Y 3D model JSmol Interactive image ChemSpider 5808 N ECHA InfoCard 100 000 371 IUPHAR BPS 5125 MeSH Uridine monophosphate PubChem CID 6030 UNII E2OU15WN0N Y CompTox Dashboard EPA DTXSID20883211 InChI InChI 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 NKey DJJCXFVJDGTHFX XVFCMESISA N NInChI 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 s1Key DJJCXFVJDGTHFX XVFCMESIBD SMILES c1cn c O nH c1 O C H 2 C H C H C H O2 COP O O O O O Properties Chemical formula C 9H 13N 2O 9P Molar mass 324 182 g mol 1 Melting point 202 C 396 F 475 K decomposes 1 Solubility in water good also in methanol 1 Acidity pKa 1 0 6 4 9 5 Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa N verify what is Y N Infobox references Contents 1 Biosynthesis 2 Effects on animal intelligence 3 In foods 4 See also 5 ReferencesBiosynthesis editUridine 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 intelligence editIn 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 foods editIn 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 editNucleoside Nucleotide DNA RNA Oligonucleotide Pyrimidine biosynthesisReferences edit a b Lide M Lide DR 1998 CRC Handbook of Chemistry and Physics 87 ed CRC Press pp 3 56 ISBN 978 0 8493 0594 8 Voet D Voet JG Pratt CW 2008 Fundamentals of Biochemistry 3rd ed John Wiley amp Sons Berg J Tymoczko JL Stryer L 2006 Biochemistry 6th ed San Francisco W H Freeman ISBN 0 7167 8724 5 Winkler JK Suttle DP July 1988 Analysis of UMP synthase gene and mRNA structure in hereditary orotic aciduria fibroblasts American Journal of Human Genetics 43 1 86 94 PMC 1715274 PMID 2837086 Holguin S Martinez J Chow C Wurtman R November 2008 Dietary uridine enhances the improvement in learning and memory produced by administering DHA to gerbils FASEB Journal 22 11 3938 46 doi 10 1096 fj 08 112425 PMC 2574024 PMID 18606862 Get Smart About What You Eat And You Might Actually Improve Your Intelligence ScienceDaily Press release July 3 2008 Wurtman RJ Cansev M Sakamoto T Ulus IH 2009 Use of phosphatide precursors to promote synaptogenesis Annual Review of Nutrition 29 59 87 doi 10 1146 annurev nutr 080508 141059 PMID 19400698 Gasser T Moyer JD Handschumacher RE August 1981 Novel single pass exchange of circulating uridine in rat liver Science 213 4509 777 8 Bibcode 1981Sci 213 777G doi 10 1126 science 7256279 PMID 7256279 Retrieved from https en wikipedia org w index php title Uridine monophosphate amp oldid 1211559160, wikipedia, wiki, book, books, library,

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