5'-Guanylyl imidodiphosphate

From Wikipedia, the free encyclopedia
Jump to navigation Jump to search
5'-Guanylyl imidodiphosphate
5'-Guanylyl imidodiphosphate.svg
Names
Preferred 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
3D model (JSmol)
ChEBI
ChemSpider
  • 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
  • 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
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 checkY☒N ?)
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[edit]

  1. ^ Guanosine 5′-β,γ-imidotriphosphate trisodium salt hydrate at Sigma-Aldrich
  2. ^ a b 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. Novartis Foundation Symposia. 176: 147–163. doi:10.1002/9780470514450.ch10. ISBN 9780470514450. 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. Bibcode:1991Sci...252.1171C. doi:10.1126/science.252.5009.1171. PMID 1851576.