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 (JSmol)	Interactive image;
ChEBI	CHEBI:78408 ;
ChemSpider	33738 ;
PubChem CID	36735;
CompTox Dashboard (EPA)	DTXSID20187842 ;
	InChI InChI=1S/C10H17N6O13P3/c11-10-13-7-4(8(19)14-10)12-2-16(7)9-6(18)5(17)3(28-9)1-27-32(25,26)29-31(23,24)15-30(20,21)22/h2-3,5-6,9,17-18H,1H2,(H,25,26)(H3,11,13,14,19)(H4,15,20,21,22,23,24)/t3-,5-,6-,9-/m1/s1 Key: UQABYHGXWYXDTK-UUOKFMHZSA-N ;
	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	522.196 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 (GDPNP) 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

Guanosine 5′-β,γ-imidotriphosphate trisodium salt hydrate at Sigma-Aldrich
Guanylyl imidodiphosphate at PubChem
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.
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.

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[1] Guanosine 5′-β,γ-imidotriphosphate trisodium salt hydrate at Sigma-Aldrich

[PubChem-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.