Chemistry:5'-Guanylyl imidodiphosphate

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5'-Guanylyl imidodiphosphate
5'-Guanylyl imidodiphosphate.svg
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
3D model (JSmol)
ChEBI
ChemSpider
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).
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Infobox references
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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

  1. Guanosine 5′-β,γ-imidotriphosphate trisodium salt hydrate at Sigma-Aldrich
  2. 2.0 2.1 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 Foundation Symposium 176 - the GTPase Superfamily. Novartis Foundation Symposia. 176. 147–163. doi:10.1002/9780470514450.ch10. ISBN 9780470514450. 
  4. Connolly, T. (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. Bibcode1991Sci...252.1171C.