Uridine monophosphate
| Uridine monophosphate | |
|---|---|
 |
|
| Identifiers | |
| CAS number | 58-97-9  |
| PubChem | 6030 |
| ChemSpider | 5808  |
| MeSH | Uridine+monophosphate |
| Jmol-3D images | Image 1 |
|
|
|
|
| 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 |
 (verify) (what is:  / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
|
| Infobox references | |
Uridine monophosphate, also known as 5'-uridylic acid and abbreviated UMP, 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 ribonucleoside monophosphate. Another common shorthand for the molecule is uridylate - the deprotonated form of the molecule, which is predominant in aqueous solution. As a substituent it takes the form of the prefix uridylyl-.
Biosynthesis
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. [2]
In humans, the orotidylate decarboxylase function is carried out by the protein UMP synthase. [3] Defective UMP synthase can result in orotic aciduria, a metabolic disorder.
Effects on animal intelligence
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.[4][5]
Uridine Monophosphate in Foods
In brain research studies such as those mentioned in this article, uridine monophosphate is used as a convenient delivery compound for uridine. Uridine is the active ingredient of the compound. A common misconception is that uridine and its compounds are not available in significant quantities from foods and must be obtained from 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's yeast or some organ meats, will provide significant quantities of it. For more information, consult the article on uridine.
References
- ^ a b M. Lide, D. R. Lide: CRC Handbook of Chemistry and Physics. 87. Auflage, S. 3-56, CRC Press, 1998, ISBN 978-0-8493-0594-8
- ^ Berg J, Tymoczko JL, Stryer L (2006). Biochemistry (6th ed. ed.). San Francisco: W. H. Freeman. ISBN 0-7167-8724-5.
- ^ Analysis of UMP synthase gene and mRNA structure in hereditary orotic aciduria fibroblasts
- ^ Holguin, S.; Martinez, J.; Chow, C.; Wurtman, R. (2008). "Dietary uridine enhances the improvement in learning and memory produced by administering DHA to gerbils". The FASEB Journal 22 (11): 3938–3946. doi:10.1096/fj.08-112425. PMC 2574024. PMID 18606862.
- ^ Get Smart About What You Eat And You Might Actually Improve Your Intelligence. ScienceDaily, July 3, 2008
See also
- Nucleoside
- Nucleotide
- DNA
- RNA
- Oligonucleotide
- Pyrimidine biosynthesis
- Ribonucleoside monophosphate
|
|||||||||||||||||||||||||||||||||
|
|||||||||||||||||||||||
 |
This biochemistry article is a stub. You can help Wikipedia by expanding it. |
