5'-Guanylyl imidodiphosphate

5'-Guanylyl imidodiphosphate
Names
	IUPAC name Guanosine 5′-(tetrahydrogen 4-imidotriphosphate)
	Systematic IUPAC name O5-{[(2R,3S,4R,5R)-5-(2-Amino-6-oxo-1,6-dihydro-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl} tetrahydrogen 2-imidotriphosphate
	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) ;
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). verify (what is ?) 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
^ ^a ^b Guanylyl imidodiphosphate at PubChem
^ Miller, J.D. & Walter, P. (1993). "A GTPase Cycle in Initiation of Protein Translocation Across the Endoplasmic Reticulum Membrane". Ciba Foundation Symposium 176 - the GTPase Superfamily. Novartis Foundation Symposia. Vol. 176. pp. 147–163. doi:10.1002/9780470514450.ch10. ISBN 9780470514450. PMID 8299417. {{cite book}}: |journal= ignored (help)
^ Connolly, T.; et al. (1991). "Requirement of GTP hydrolysis for dissociation of the signal recognition particle from its receptor". Science. 252 (5009): 1171–1173. Bibcode:1991Sci...252.1171C. doi:10.1126/science.252.5009.1171. PMID 1851576. S2CID 42899156.

Names

IUPAC name Guanosine 5′-(tetrahydrogen 4-imidotriphosphate)
Systematic IUPAC name O⁵-{[(2R,3S,4R,5R)-5-(2-Amino-6-oxo-1,6-dihydro-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl} tetrahydrogen 2-imidotriphosphate
Other names GppNHp; GppNP; GMP-Pnp; GDP-NP Guanylyl imidodiphosphate 5-Guanylylimidodiphosphate 5′-Guanylyliminodiphosphonate
Identifiers
CAS Number	34273-04-6^Y 148892-91-5 (trisodium salt)^[1]^N
3D model (JSmol)	Interactive image
ChEBI	CHEBI:78408^N
ChemSpider	33738^N
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^N Key: UQABYHGXWYXDTK-UUOKFMHZSA-N^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). N verify (what is ^YN ?) Infobox references