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( R e d i r e c t e d f r o m G u a n y l i c a c i d )
Guanosine monophosphate
Names
IUPAC name
5 ′-Guanylic acid
Systematic IUPAC name
[(2 R ,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
Identifiers
CAS Number
3D model (JSmol )
Abbreviations
GMP
ChEMBL
ChemSpider
ECHA InfoCard
100.001.453
E number
E626 (flavour enhancer)
IUPHAR/BPS
MeSH
Guanosine+monophosphate
PubChem CID
UNII
CompTox Dashboard (EPA )
C1=NC2=C(N1[C@H]3[C@@H]([C@@H]([C@H](O3)COP(=O)(O )O)O)O)NC(=NC2=O)N
Properties
Chemical formula
C 10 H 14 N 5 O 8 P
Molar mass
363.223 g·mol−1
Acidity (p K a )
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).
Infobox references
Chemical compound
Guanosine monophosphate (GMP ), also known as 5 ′-guanidylic acidor guanylic acid (conjugate base guanylate ), is a nucleotide that is used as a monomer 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 ; hence it is a ribonucleotide monophosphate. Guanosine monophosphate is commercially produced by microbial fermentation.[1]
As an acyl substituent , it takes the form of the prefix guanylyl- .
De novo synthesis[ edit ]
GMP synthesis starts with D -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, the glutamine analogue DON can be used.[3]
GMP can also exist as a cyclic structure known as cyclic GMP . Within certain cells the enzyme guanylyl cyclase makes cGMP from GTP.
cGMP plays an important role in mediating hormonal signaling.[2]
Sources [ edit ]
GMP was originally identified as the umami substance in dried shiitake 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 into AICA ribonucleotide , which is then converted chemically to GMP.[5] Tapioca starch is a possible sugar source.[6]
Food additive [ edit ]
Guanosine monophosphate is known as E number reference E626.[7] 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.[7] 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, the glutamic acid is likely provided as part of another ingredient, such as a processed soy protein complex (hydrolyzed soy protein), autolyzed yeast , or soy sauce .
See also [ edit ]
Disodium guanylate
Disodium inosinate
Inosinic acid
Glutamate flavoring
Kikunae Ikeda
Umami
Ajinomoto
Tien Chu Ve-Tsin
Glutamic acid
Disodium glutamate
Monopotassium glutamate
Adenosine monophosphate
Hypoxanthine-guanine phosphoribosyltransferase
Ribonucleoside
References [ edit ]
^ a b Voet, Donald; Voet, Judith G. (2012). Biochemistry . USA: John Wiley & Sons Inc. pp. 1107–1109. ISBN 978-0-470-57095-1 .
^ Ahluwalia GS et al. Metabolism and action of amino acid analog anti-cancer agents ” , in Pharmac. Ther. (1990) 46: 243-271
^ Kurihara, K (2015). "Umami the Fifth Basic Taste: History of Studies on Receptor Mechanisms and Role as a Food Flavor" . BioMed Research International . 2015 : 189402. doi :10.1155/2015/189402 . PMC 4515277 . PMID 26247011 .
^ Kinoshita, Kazumoto; Shiro, Teruo; Yamazaki, Akihiro; Kumashiro, Izumi; Takenishi, Tadao; Tsunoda, Toshinao (July 1967). "Industrial production of disodium 5?-guanylate". Biotechnology and Bioengineering . 9 (3 ): 329–342. doi :10.1002/bit.260090306 . S2CID 84216811 .
^ Conn, Helen (1 February 1992). " "Umami": The Fifth Basic Taste". Nutrition & Food Science . 92 (2 ): 21–23. doi :10.1108/EUM0000000000953 .
^ a b "Additive categories | CEFF" . www.ceff.info . Retrieved 2021-11-30 .
R e t r i e v e d f r o m " https://en.wikipedia.org/w/index.php?title=Guanosine_monophosphate&oldid=1221282367 "
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