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| Names | |
|---|---|
| IUPAC name 5′-Guanylic acid | |
| Systematic IUPAC name [(2R,3S,4R,5R)-5-(2-Amino-6-oxo-1,6-dihydro-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl dihydrogen phosphate | |
Other names
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| Identifiers | |
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3D model (JSmol) | |
| Abbreviations | GMP |
| ChEBI | |
| ChEMBL | |
| ChemSpider |
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| DrugBank | |
| ECHA InfoCard | 100.001.453 |
| E number | E626(flavour enhancer) |
| KEGG | |
| MeSH | Guanosine+monophosphate |
| UNII | |
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| Properties | |
| C10H14N5O8P | |
| Molar mass | 363.223 g·mol−1 |
| Acidity (pKa) | 0.7, 2.4, 6.1, 9.4 |
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |
Guanosine monophosphate (GMP), also known as5′-guanidylic acid orguanylic acid (conjugate baseguanylate), is anucleotide that is used as amonomer inRNA. It is anester ofphosphoric acid with thenucleosideguanosine. GMP consists of thephosphategroup, thepentosesugarribose, and thenucleobaseguanine; hence it is aribonucleotide monophosphate. Guanosine monophosphate is commercially produced by microbial fermentation.[1]
As anacylsubstituent, it takes the form of the prefixguanylyl-.
GMP synthesis starts withD-ribose 5′-phosphate, a product of the pentose phosphate pathway. The synthesis proceeds by the gradual formation of the purine ring on carbon-1 of ribose, with CO2, glutamine, glycine, aspartate and one-carbon derivatives of tetrahydrofolate donating various elements towards the building of the ring.[2]
As inhibitor of guanosine monophosphate synthesis in experimental models, theglutamine analogueDON can be used.[3]
GMP can also exist as a cyclic structure known ascyclic GMP. Within certain cells the enzyme guanylyl cyclase makes cGMP from GTP.
cGMP plays an important role in mediating hormonal signaling.[2]
GMP was originally identified as the umami substance in driedshiitake mushroom. The drying process significantly increases GMP content with the breakdown of RNA. It can be found in a number of other mushrooms.[4]
Industrial production is based on fermentation: a bacterium converts sugars intoAICA ribonucleotide, which is then converted chemically to GMP.[5]Tapioca starch is a possible sugar source.[6]
Guanosine monophosphate is known asE number reference E626.[7] In the form of itssalts, such asdisodium guanylate (E627),dipotassium guanylate (E628) andcalcium guanylate (E629), arefood additives used asflavor enhancers to provide theumami taste.[7] It is often used in synergy withdisodium inosinate; the combination is known asdisodium 5′-ribonucleotides. Disodium guanylate is often found in instant noodles, potato chips and snacks, savoury rice, tinned vegetables, cured meats, and packet soup.
As it is a fairly expensive additive, it is usually not used independently ofglutamic acid ormonosodium glutamate (MSG), which also contribute umami. If inosinate and guanylate salts are present in a list of ingredients but MSG does not appear to be, the glutamic acid is likely provided as part of another ingredient, such as a processed soy protein complex (hydrolyzed soy protein),autolyzed yeast, orsoy sauce.
