Guanosine monophosphate

Guanosine monophosphate
Names
IUPAC name
5′-Guanylic acid
Systematic IUPAC name
[(2R,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
3D model (JSmol)
Abbreviations GMP
ChEMBL
ChemSpider
ECHA InfoCard 100.001.453
E number E626 (flavour enhancer)
MeSH Guanosine+monophosphate
UNII
  • Nc1nc2n(cnc2c(=O)[nH]1)[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1O
Properties
C10H14N5O8P
Molar mass 363.223 g·mol−1
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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Infobox references

Guanosine monophosphate (GMP), also known as 5′-guanidylic acid or 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.

As an acyl substituent, it takes the form of the prefix guanylyl-.

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