5'-Guanylyl imidodiphosphate

5'-Guanylyl imidodiphosphate

Names
IUPAC name [[[[(2R,3S,4R,5R)-5-(2-amino-6-oxo-3H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl]amino]phosphonic acid
Other names GppNHp; GppNP; GMP-Pnp; GDP-NP Guanylyl imidodiphosphate 5-Guanylylimidodiphosphate 5'-Guanylyliminodiphosphonate
Identifiers
CAS Number	34273-04-6 148892-91-5 (trisodium salt)[1]
3D model (Jmol)	Interactive image
ChEBI	CHEBI:78408
PubChem	36735
SMILES C1=NC2=C(N1[C@H]3[C@@H]([C@@H]([C@H](O3)COP(=O)(O)OP(=O)(NP(=O)(O)O)O)O)O)NC(=NC2=O)N
Properties
Chemical formula	C10H17N6O13P3
Molar mass	522.20 g·mol^−1
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

5'-Guanylyl imidodiphosphate is a purine nucleotide. It is an analog of guanosine triphosphate in which one of the oxygen atoms is replaced with an amine, producing a non-hydrolyzable functional group. Guanylyl imidodiphosphate binds tightly to G-proteins in the presence of Mg²⁺.^[2] Guanylyl imidodiphosphate is a potent stimulator of adenylate cyclase.^[2] It is often used in studies of protein synthesis.^[3][4]

References

1. Guanosine 5′-β,γ-imidotriphosphate trisodium salt hydrate at Sigma-Aldrich
2. Guanylyl imidodiphosphate at PubChem
3. Miller, J.D. & Walter, P. (1993). "A GTPase cycle in initiation of protein translocation across the endoplasmic reticulum membrane". Ciba Found. Symp. 176: 147–163. PMID 8299417.
4. Connolly, T.; et al. (1991). "Requirement of GTP hydrolysis for dissociation of the signal recognition particle from its receptor". Science. 252 (5009): 1171–1173. doi:10.1126/science.252.5009.1171. PMID 1851576.