Guanosín monofosfato

Guanosín monofosfato
Modelo de esferas macizas da guanosina monofosfato
Nome IUPAC

[(2R,3S,4R,5R)-5-(2-Amino-6-oxo-3H-purin-9-il)-3,4-dihidroxioxolan-2-il]metil dihidróxeno fosfato

Outros nomes

Ácido 5'-guanidílico,
ácido 5'-guanílico,
número E E626

Identificadores
Abreviaturas GMP
Número CAS 85-32-5
PubChem 6804
MeSH Guanosine+monophosphate
ChEMBL CHEMBL604603
Imaxes 3D Jmol Image 1
Propiedades
Fórmula molecular C10H14N5O8P
Masa molecular 363,22 g/mol
Acidez (pKa) 0,7, 2,4, 6,1, 9,4

Se non se indica outra cousa, os datos están tomados en condicións estándar de 25 °C e 100 kPa.

O guanosín monofosfato, tamén chamado monofosfato de guanosina, ácido guanílico ou ácido 5'-guanílico, abreviado como GMP, é un nucleótido que forma parte do ARN. É un éster en posición 5' do ácido fosfórico co nucleósido guanosina. O GMP consta do azucre ribosa unido por enlace N-glicosídico á base nitroxenada guanina e un fosfato.

Como grupo substituínte desígnase co prefixo guanilil-. Os seus sales chámanse guanilatos

A súa función biolóxica principal é ser un dos catro nucleótidos que forman parte do ARN, xunto co CMP, UMP e AMP.

En modelos experimentais úsase o análogo da glutamina DON como inhibidor da síntese de GMP.[1]

Usos

O guanosín monofosfato en forma de sales que se utilizan como aditivo alimentario. Estes sales son o guanilato disódico (E627), guanilato dipotásico (E628) e guanilato cálcico (E629), que son potenciadores do sabor que dan sabor umami, un dos sabores básicos.[2]. Xeralmente úsanse xunto con inosinato disódico; a combinación de ambos chámase disodio 5'-ribonucleótido. O guanilato disódico atópase con frecuencia como aditivo en fideos instantáneos, patatas fritidas e outros aperitivos, arroz saborizado, vexetais en conserva, carnes curadas, e sobres de sopa.

Como é un aditivo bastante caro é raro que se use só ; normalmente úsase xunto con ácido glutámico ou glutamato monosódico (MSG), que tamén contribúen ao sabor umami. Se non aparece o ácido glutámico nunha lista de ingredientes dun alimento na que hai guanilatos ou inosinatos é probablemente porque o ácido glutámico xa forma parte doutro compoñente do alimento, como complexos de proteína de soia procesados (proteína de soia hidrolizada), lévedos autolisados ou prebe de soia.

Véxase tamén

Notas

  1. ↑ Ahluwalia GS et al. Metabolism and action of amino acid analog anti-cancer agents ”, in Pharmac. Ther. (1990) 46: 243-271
  2. ↑ Cairoli P, Pieraccini S, Sironi M, Morelli CF, Speranza G, Manitto P (2008). "Studies on umami taste. Synthesis of new guanosine 5'-phosphate derivatives and their synergistic effect with monosodium glutamate". J. Agric. Food Chem. 56 (3): 1043–50. ISSN 0021-8561. PMID 18181569. doi:10.1021/jf072803c. 

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