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Revision as of 19:52, 20 August 2011 editLuckas-bot (talk | contribs)929,662 editsm r2.7.1) (robot Adding: gl:Guanosín monofosfato← Previous edit		Latest revision as of 00:05, 29 April 2024 edit undo46.7.156.41 (talk) Changed nucleoside to nucleoside because GMP does include a phosphateTags: Mobile edit Mobile web edit
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			{{Distinguish|Cyclic guanosine monophosphate}}
	{{Chembox		{{Chembox
			| Verifiedfields = changed
	| verifiedrevid = 416488838
			| Watchedfields = changed
	|ImageFile=GMP chemical structure.png
			| verifiedrevid = 445871473
	|ImageSize=200px
			| ImageFile = Guanosinmonophosphat protoniert.svg
	|ImageFile1 = Guanosine-monophosphate-space-filling.png
	|ImageSize1 = 200px		| ImageSize = 200px
	|ImageName1 = Space-filling model of guanosine monophosphate		| ImageFile1 = Guanosine-monophosphate-3D-spacefill.png
			| ImageSize1 = 200px
	|IUPACName= <small>methyl dihydrogen phosphate</small> {{Citation needed|date=April 2010}}
			| ImageName1 = Space-filling model of guanosine monophosphate
	|OtherNames=5'-Guanidylic acid,<br>5'-Guanylic acid,<br>] E626
			| IUPACName = 5′-Guanylic acid
	|Section1= {{Chembox Identifiers
			| SystematicName = methyl dihydrogen phosphate
	| Abbreviations = GMP
			| OtherNames = {{Unbulleted list|5′-Guanidylic acid|] E626}}
	| CASNo_Ref = {{cascite|correct|CAS}}
			|Section1={{Chembox Identifiers
	| CASNo=85-32-5
			| IUPHAR_ligand = 5123
	| PubChem=6804
			| Abbreviations = GMP
	| SMILES=C1=NC2=C(N13(((O3)COP(=O)(O)O)O)O)NC(=NC2=O)N
			| CASNo_Ref = {{cascite|correct|CAS}}
	| MeSHName=Guanosine+monophosphate
			| CASNo = 85-32-5
			| UNII_Ref = {{fdacite|correct|FDA}}
			| UNII = 16597955EP
			| PubChem = 135398631
			| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
			| ChemSpiderID = 6545
			| ChEMBL_Ref = {{ebicite|changed|EBI}}
			| ChEMBL = 604603
			| SMILES = C1=NC2=C(N13(((O3)COP(=O)(O)O)O)O)NC(=NC2=O)N
			| MeSHName = Guanosine+monophosphate
	}}		}}
	|Section2= {{Chembox Properties		|Section2={{Chembox Properties
			| C=10|H=14|N=5|O=8|P=1
	| Formula=C<sub>10</sub>H<sub>14</sub>N<sub>5</sub>O<sub>8</sub>P
			| pKa= 0.7, 2.4, 6.1, 9.4
	| MolarMass=363.22 g/mol
			| Appearance=
	| pKa= 0.7, 2.4, 6.1, 9.4
	| Appearance=		| Density=
	| Density=		| MeltingPt=
	| MeltingPt=		| BoilingPt=
	| BoilingPt=		| Solubility=
	| Solubility=
	}}		}}
	|Section3= {{Chembox Hazards		|Section3={{Chembox Hazards
	| MainHazards=		| MainHazards=
	| FlashPt=		| FlashPt=
			| AutoignitionPt =
	| Autoignition=
	}}		}}
	}}		}}
			'''Guanosine monophosphate''' ('''GMP'''), also known as '''5′-guanidylic acid''' or '''guanylic acid''' (] '''guanylate'''), is a ] that is used as a ] in ]. It is an ] of ] with the ] ]. GMP consists of the ] ], the ] ] ], and the ] ]; hence it is a ] monophosphate. Guanosine monophosphate is commercially produced by microbial fermentation.<ref>{{cite web|url=http://www.vrg.org/blog/2011/03/21/disodium-inosinate-and-disodium-guanylate-are-all-vegetable-flavor-enhancers/|title=The Vegetarian Resource Group Blog|website=www.vrg.org|access-date=25 April 2018}}</ref>
	{{Refimprove|date=April 2010}}
	'''Guanosine monophosphate''', also known as '''5'-guanidylic acid''' or '''guanylic acid''' and abbreviated '''GMP''', is a ] that is found in ]. It is an ] of ] with the ] ]. GMP consists of the ] ], the ] ] ], and the ] ]; hence it is a ]. Guanosine monophosphate is produced from dried fish or dried seaweed.{{Citation needed|date=August 2007}}
			As an ] ], it takes the form of the prefix '''guanylyl-'''.
	Guanosine monophosphate in the form of its ], such as ] (]), ] (E628) and ] (E629), are ]s used as ]s to provide the ] taste. It is often used in synergy with ]; the combination is known as ]. Disodium guanylate is often found in instant noodles, potato chips and snacks, savoury rice, tinned vegetables, cured meats, and packet soup.
			==''De novo'' synthesis==
	As it is a fairly expensive additive, it is usually not used independently of ] or ] (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), ] or ].
			GMP synthesis starts with <small>D</small>-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 CO<sub>2</sub>, glutamine, glycine, aspartate and one-carbon derivatives of tetrahydrofolate donating various elements towards the building of the ring.<ref name=":0">{{cite book |title=Biochemistry |last1=Voet |first1=Donald |last2=Voet |first2=Judith G. |publisher=John Wiley & Sons Inc. |year=2012 |isbn=978-0-470-57095-1 |location=USA |pages=1107–1109}}</ref>
	As inhibitor of guanosine monophosphate synthesis in experimentell models the ] analogue ] can be used.<ref name="Ahluwalia"> ''Ahluwalia GS et al. , ''in Pharmac. Ther. (1990) 46: 243-271 '' </ref>
			]As inhibitor of guanosine monophosphate synthesis in experimental models, the ] analogue ] can be used.<ref name="Ahluwalia">''Ahluwalia GS et al. , ''in Pharmac. Ther. (1990) 46: 243-271 </ref>
			==cGMP==
	As an ] ] it takes the form of the prefix '''guanylyl-'''.
			GMP can also exist as a cyclic structure known as ]. Within certain cells the enzyme guanylyl cyclase makes cGMP from GTP.
	==See also==
	* ]
			cGMP plays an important role in mediating hormonal signaling.<ref name=":0" />
	* ]
			== Sources ==
			GMP was originally identified as the umami substance in dried ] mushroom. The drying process significantly increases GMP content with the breakdown of RNA. It can be found in a number of other mushrooms.<ref name="pmid26247011">{{cite journal |last1=Kurihara |first1=K |title=Umami the Fifth Basic Taste: History of Studies on Receptor Mechanisms and Role as a Food Flavor. |journal=BioMed Research International |date=2015 |volume=2015 |pages=189402 |doi=10.1155/2015/189402 |pmid=26247011|pmc=4515277 |doi-access=free }}</ref><!-- ah well, where else can you fidn this kind of trivia, if not for hindawi? -->
			Industrial production is based on fermentation: a bacterium converts sugars into ], which is then converted chemically to GMP.<ref>{{cite journal |last1=Kinoshita |first1=Kazumoto |last2=Shiro |first2=Teruo |last3=Yamazaki |first3=Akihiro |last4=Kumashiro |first4=Izumi |last5=Takenishi |first5=Tadao |last6=Tsunoda |first6=Toshinao |title=Industrial production of disodium 5?-guanylate |journal=Biotechnology and Bioengineering |date=July 1967 |volume=9 |issue=3 |pages=329–342 |doi=10.1002/bit.260090306|s2cid=84216811 }}</ref> ] is a possible sugar source.<ref>{{cite journal |last1=Conn |first1=Helen |title="Umami": The Fifth Basic Taste |journal=Nutrition & Food Science |date=1 February 1992 |volume=92 |issue=2 |pages=21–23 |doi=10.1108/EUM0000000000953}}</ref>
			== Food additive ==
			Guanosine monophosphate is known as ] reference E626.<ref name=":1">{{Cite web|title=Additive categories {{!}} CEFF|url=https://www.ceff.info/en/additives/categories?category_id=15&do=categoryDetail|access-date=2021-11-30|website=www.ceff.info}}</ref> In the form of its ], such as ] (]), ] (E628) and ] (E629), are ]s used as ]s to provide the ] taste.<ref name=":1" /> It is often used in synergy with ]; the combination is known as ]. 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 ] or ] (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), ], or ].
			== See also ==
			{{Columns-list|colwidth=16em|
			* ]
			* ]
			* ]
			* ]
			* ]
			* ]
	* ]		* ]
			* ]
			* ]
			* ]
			* ]
			* ]
			* ]
			* ]
			* ]
			}}
	==References==		==References==
	<references/>		<references />
	{{Nucleobases, nucleosides, and nucleotides}}		{{Nucleobases, nucleosides, and nucleotides}}
			{{Purinergics}}
			{{DEFAULTSORT:Guanosine phosphate1}}
	{{DEFAULTSORT:Guanosine Monophosphate}}
	]		]
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