Guanosine monophosphate
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| Names | |
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| IUPAC name
[(2R,3S,4R,5R)-5-(2-Amino-6-oxo-3H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl dihydrogen phosphate
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| Other names | |
| Identifiers | |
3D model (JSmol)
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| Abbreviations | GMP |
| ECHA InfoCard | 100.001.453 |
| E number | E626 (flavour enhancer) |
| MeSH | Guanosine+monophosphate |
PubChem CID
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CompTox Dashboard (EPA)
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| Properties | |
| C10H14N5O8P | |
| Molar mass | 363.22 g/mol |
| Acidity (pKa) | 0.7, 2.4, 6.1, 9.4 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Guanosine monophosphate, also known as 5'-guanidylic acid or guanylic acid and abbreviated GMP, is a nucleotide that is found in RNA. It is an ester of phosphoric acid with the nucleoside guanosine. GMP consists of the phosphate group, the pentose sugar ribose, and the nucleobase guanine. Guanosine monophosphate is produced from dried fish or dried seaweed.[citation needed]
Guanosine monophosphate in the form of its salts, such as disodium guanylate (E627), dipotassium guanylate (E628) and calcium guanylate (E629), are food additives used as flavor enhancers to provide the umami taste. It is often used in synergy with disodium inosinate; the combination is known as disodium 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 of glutamic acid or monosodium 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, it is likely that glutamic acid is provided as part of another ingredient, such as a processed soy protein complex (hydrolyzed soy protein), autolyzed yeast or soy sauce.
As inhibitor for experimentell models the glutamine analogue DON can be used.[1]
See also
References
- ^ Ahluwalia GS et al. Metabolism and action of amino acid analog anti-cancer agents ”, in Pharmac. Ther. (1990) 46: 243-271