uridine monophosphate.pdf

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Uridine monophosphate

Identifiers

CAS

number

58-97-9

PubChem 6030

ChemSpider 5808

MeSH Uridine+monophosphate

Jmol-3D

images

Image 1

(http://chemapps.stolaf.edu

/jmol/jmol.php?model=c1cn%28c

%28%3DO

%29%5BnH%5Dc1%3DO

%29%5BC%40H%5D2%5BC

%40%40H%5D%28%5BC%40

%40H%5D%28%5BC%40H

%5D%28O2%29COP%28%3DO

%29%28O%29O%29O%29O)

Properties

Molecular

formula

C9H13N2O9P

Molar mass 324.181

Melting

point 202 C (dec.)[1]

Solubility in

water

good, also in methanol [1]

Acidity

(pKa)

1.0, 6.4, 9.5

Uridine monophosphateFrom Wikipedia, the free encyclopedia

Uridine monophosphate, also known as5'-uridylic acidand abbreviated UMP, isa nucleotide that is used as a monomer inRNA. It is an ester of phosphoric acid with

the nucleoside uridine. UMP consists of thephosphate group, the pentose sugar ribose,and the nucleobase uracil; hence, it is aribonucleoside monophosphate. Anothercommon shorthand for the molecule isuridylate- the deprotonated form of themolecule, which is predominant in aqueoussolution. As a substituent it takes the formof the prefix uridylyl-.

Contents

1 Biosynthesis2 Effects on animal intelligence3 Uridine Monophosphate in Foods4 References5 See also

Biosynthesis

Uridine monophosphate is formed fromOrotidine 5'-monophosphate (orotidylicacid) in a decarboxylation reactioncatalyzed by the enzyme orotidylatedecarboxylase. Uncatalyzed, thedecarboxylation reaction is extremely slow(estimated to occur on average one timeper 78 million years). Adequately catalyzed,

the reaction takes place once per second,an increase of 10

17-fold.

[2]

In humans, the orotidylate decarboxylasefunction is carried out by the protein UMP

synthase.[3]

Defective UMP synthase canresult in orotic aciduria, a metabolicdisorder.

SMILES

InChI

ine monophosphate - Wikipedia, the free encyclopedia https://en.wikipedia.org/wiki/Uridine_monopho

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Except where noted otherwise, data are given

for materials in their standard state (at 25 C,

100 kPa)

Infobox references

Effects on animalintelligence

In a study, gerbils fed a combination ofuridine monophosphate, choline, anddocosahexaenoic acid (DHA) were found tohave significantly improved performance in running mazes over those not fed the

supplements, implying an increase in cognitive function.[4][5]

Uridine Monophosphate in Foods

In brain research studies such as those mentioned in this article, uridinemonophosphate is used as a convenient delivery compound for uridine. Uridine is theactive ingredient of the compound. A common misconception is that uridine and itscompounds are not available in significant quantities from foods and must be obtainedfrom expensive supplements or prescription drugs. This is not so. Uridine

monophosphate is a major component of RNA. Any food rich in RNA, such as Brewer'syeast or some organ meats, will provide significant quantities of it. For moreinformation, consult the article on uridine.

References

^ abM. Lide, D. R. Lide: CRC Handbook of Chemistry and Physics.87. Auflage, S. 3-56,CRC Press, 1998, ISBN 978-0-8493-0594-8

1.

^Berg J, Tymoczko JL, Stryer L (2006).Biochemistry(6th ed. ed.). San Francisco: W. H.Freeman. ISBN 0-7167-8724-5.

2.

^Analysis of UMP synthase gene and mRNA structure in hereditary orotic aciduria

fibroblasts (http://www.pubmedcentral.nih.gov/articlerender.fcgi?artid=1715274)

3.

^Holguin, S.; Martinez, J.; Chow, C.; Wurtman, R. (2008). "Dietary uridine enhances theimprovement in learning and memory produced by administering DHA to gerbils"(//www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=2574024) . The

FASEB Journal22(11): 39383946. DOI:10.1096/fj.08-112425 (http://dx.doi.org/10.1096%2Ffj.08-112425) . PMC 2574024 (//www.ncbi.nlm.nih.gov/pmc/articles/PMC2574024/?tool=pmcentrez) . PMID 18606862 (//www.ncbi.nlm.nih.gov/pubmed/18606862) . //www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=2574024.

4.

^Get Smart About What You Eat And You Might Actually Improve Your Intelligence.ScienceDaily, July 3, 2008 (http://www.sciencedaily.com/releases/2008/07

/080702150706.htm)

5.

See also

NucleosideNucleotideDNARNAOligonucleotidePyrimidine biosynthesis


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Ribonucleoside monophosphate

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This page was last modified on 10 May 2012 at 01:51.Text is available under the Creative Commons Attribution-ShareAlike License;additional terms may apply. See Terms of use for details.Wikipedia is a registered trademark of the Wikimedia Foundation, Inc., anon-profit organization.


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