Uridine monophosphate
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| Names | |
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| IUPAC name
[(2R,3S,4R,5R)-5-(2,4-Dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl dihydrogen phosphate
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| Other names
Uridylic acid; Uridine 5'-monophosphate; 5'-Uridylic acid; Uridine 5'-phosphate; Uridine phosphate; 5'-UMP; Uridine 5'-phosphoric acid
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| Identifiers | |
58-97-9  |
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| ChemSpider | 5808  |
| 5125 | |
| Jmol 3D model | Interactive image |
| MeSH | Uridine+monophosphate |
| PubChem | 6030 |
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| Properties | |
| C9H13N2O9P | |
| Molar mass | 324.18 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 |
| Vapor pressure | {{{value}}} |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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 verify (what is ?) |
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| 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-. The deoxy form is abbreviated dUMP.
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]
In foods
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. However, uridine in RNA is not bioavailable, since it is almost entirely destroyed in the liver and gastrointestinal tract.[7] Thus no food, when consumed, has ever reliably been shown to raise blood uridine levels except mothers' milk or infant formulas which contain uridine in the form of uridine monophosphate instead of as RNA.[8]
See also
References
- ↑ 1.0 1.1 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
- ↑ Lua error in package.lua at line 80: module 'strict' not found.
- ↑ Analysis of UMP synthase gene and mRNA structure in hereditary orotic aciduria fibroblasts
- ↑ Lua error in package.lua at line 80: module 'strict' not found.
- ↑ Get Smart About What You Eat And You Might Actually Improve Your Intelligence. ScienceDaily, July 3, 2008
- ↑ Lua error in package.lua at line 80: module 'strict' not found.
- ↑ Lua error in package.lua at line 80: module 'strict' not found.
- ↑ Lua error in package.lua at line 80: module 'strict' not found.
