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Guanosine monophosphate (GMP), also known as 5′-guanidylic acid or guanylic acid (
As inhibitor of guanosine monophosphate synthesis in experimental models, the glutamine analogue DON can be used.''Ahluwalia GS et al
Metabolism and action of amino acid analog anti-cancer agents ”
''in Pharmac. Ther. (1990) 46: 243-271
conjugate base
A conjugate acid, within the Brønsted–Lowry acid–base theory, is a chemical compound formed when an acid donates a proton () to a base—in other words, it is a base with a hydrogen ion added to it, as in the reverse reaction it loses a ...
guanylate), is a nucleotide
Nucleotides are organic molecules consisting of a nucleoside and a phosphate. They serve as monomeric units of the nucleic acid polymers – deoxyribonucleic acid (DNA) and ribonucleic acid (RNA), both of which are essential biomolecu ...
that is used as a monomer
In chemistry, a monomer ( ; '' mono-'', "one" + '' -mer'', "part") is a molecule that can react together with other monomer molecules to form a larger polymer chain or three-dimensional network in a process called polymerization.
Classification
...
in RNA. It is an ester
In chemistry, an ester is a compound derived from an oxoacid (organic or inorganic) in which at least one hydroxyl group () is replaced by an alkoxy group (), as in the substitution reaction of a carboxylic acid and an alcohol. Glycerides ...
of phosphoric acid with the nucleoside guanosine. GMP consists of the phosphate
In chemistry, a phosphate is an anion, salt, functional group or ester derived from a phosphoric acid. It most commonly means orthophosphate, a derivative of orthophosphoric acid .
The phosphate or orthophosphate ion is derived from phosph ...
group, the pentose
In chemistry, a pentose is a monosaccharide (simple sugar) with five carbon atoms. The chemical formula of many pentoses is , and their molecular weight is 150.13 g/mol.sugar
Sugar is the generic name for sweet-tasting, soluble carbohydrates, many of which are used in food. Simple sugars, also called monosaccharides, include glucose, fructose, and galactose. Compound sugars, also called disaccharides or do ...
ribose
Ribose is a simple sugar and carbohydrate with molecular formula C5H10O5 and the linear-form composition H−(C=O)−(CHOH)4−H. The naturally-occurring form, , is a component of the ribonucleotides from which RNA is built, and so this com ...
, and the nucleobase
Nucleobases, also known as ''nitrogenous bases'' or often simply ''bases'', are nitrogen-containing biological compounds that form nucleosides, which, in turn, are components of nucleotides, with all of these monomers constituting the basi ...
guanine
Guanine () ( symbol G or Gua) is one of the four main nucleobases found in the nucleic acids DNA and RNA, the others being adenine, cytosine, and thymine ( uracil in RNA). In DNA, guanine is paired with cytosine. The guanine nucleoside is ...
; hence it is a ribonucleoside A ribonucleoside is a type of nucleoside including ribose as a component.
One example of a ribonucleoside is cytidine
Cytidine (symbol C or Cyd) is a nucleoside molecule that is formed when cytosine is attached to a ribose ring (also known as ...
monophosphate. Guanosine monophosphate is commercially produced by microbial fermentation.
As an acyl substituent
A substituent is one or a group of atoms that replaces (one or more) atoms, thereby becoming a moiety in the resultant (new) molecule. (In organic chemistry and biochemistry, the terms ''substituent'' and ''functional group'', as well as '' side ...
, it takes the form of the prefix guanylyl-.
''De novo'' synthesis
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 ringAs inhibitor of guanosine monophosphate synthesis in experimental models, the glutamine analogue DON can be used.''Ahluwalia GS et alMetabolism and action of amino acid analog anti-cancer agents ”
''in Pharmac. Ther. (1990) 46: 243-271
cGMP
GMP can also exist as a cyclic structure known ascyclic GMP
Cyclic guanosine monophosphate (cGMP) is a cyclic nucleotide derived from guanosine triphosphate (GTP). cGMP acts as a second messenger much like cyclic AMP. Its most likely mechanism of action is activation of intracellular protein kinases in ...
. Within certain cells the enzyme guanylyl cyclase makes cGMP from GTP.
cGMP plays an important role in mediating hormonal signaling.
Food additive
Guanosine monophosphate is known asE number
E numbers ("E" stands for "Europe") are codes for substances used as food additives, including those found naturally in many foods such as vitamin C, for use within the European Union (EU) and European Free Trade Association (EFTA). Commonly ...
reference E626. In the form of its salts, such as disodium guanylate
Disodium guanylate, also known as sodium 5'-guanylate and disodium 5'-guanylate, is a natural sodium salt of the flavor enhancing nucleotide guanosine monophosphate (GMP). Disodium guanylate is a food additive with the E number E627. It is commo ...
( E627), dipotassium guanylate
Dipotassium guanylate is a compound with formula K2(C10H12O4N5PO4). It is a potassium salt of guanylic acid.
As a food additive, it is used as a flavor enhancer and has the E number
E numbers ("E" stands for "Europe") are codes for substan ...
(E628) and calcium guanylate
Calcium guanylate is a compound with formula Ca(C10H12O4N5PO4). It is the calcium salt of guanylic acid. It is present in all living cells as part of RNA, and is commercially prepared from yeast extract or fish.
As a food additive, it is used a ...
(E629), are food additive
Food additives are substances added to food to preserve Taste, flavor or enhance taste, appearance, or other sensory qualities. Some additives have been used for centuries as part of an effort to preserve food, for example vinegar (pickling), sal ...
s 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
Glutamic acid (symbol Glu or E; the ionic form is known as glutamate) is an α-amino acid that is used by almost all living beings in the biosynthesis of proteins. It is a non-essential nutrient for humans, meaning that the human body can synt ...
or monosodium glutamate
Monosodium glutamate (MSG), also known as sodium glutamate, is the sodium salt of glutamic acid. MSG is found naturally in some foods including tomatoes and cheese in this glutamic acid form. MSG is used in cooking as a flavor enhancer ...
(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
Yeast extracts consist of the cell contents of yeast without the cell walls; they are used as food additives or flavorings, or as nutrients for bacterial culture media. They are often used to create savory flavors and umami taste sensations, an ...
, or soy sauce
Soy sauce (also called simply soy in American English and soya sauce in British English) is a liquid condiment of Chinese origin, traditionally made from a fermented paste of soybeans, roasted grain, brine, and ''Aspergillus oryzae'' or '' As ...
.See also
References