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Merck

M3509

Sigma-Aldrich

β,γ-Methyleneguanosine 5′-triphosphate sodium salt

≥98% (HPLC)

Sinónimos:

GMPPCP, GppCp, Guanosine-5′-[(β,γ)-methyleno]triphosphate sodium salt

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About This Item

Fórmula empírica (notación de Hill):
C11H18N5O13P3 · xNa+
Número de CAS:
Peso molecular:
521.21 (free acid basis)
MDL number:
UNSPSC Code:
41106305
PubChem Substance ID:
NACRES:
NA.51

biological source

synthetic (organic)

assay

≥98% (HPLC)

form

powder

solubility

water: 50 mg/mL, clear, colorless

storage temp.

−20°C

SMILES string

[Na].NC1=NC(=O)c2ncn(C3OC(COP(O)(=O)OP(O)(=O)CP(O)(O)=O)C(O)C3O)c2N1

InChI

1S/C11H18N5O13P3.Na.H/c12-11-14-8-5(9(19)15-11)13-2-16(8)10-7(18)6(17)4(28-10)1-27-32(25,26)29-31(23,24)3-30(20,21)22;;/h2,4,6-7,10,17-18H,1,3H2,(H,23,24)(H,25,26)(H2,20,21,22)(H3,12,14,15,19);;

InChI key

LJQPGKRRFLMZPX-UHFFFAOYSA-N

General description

βγ-Methyleneguanosine 5′-triphosphate (GMPPCP, GppCp) is a non-hydrolyzable analog of GTP.

Application

βγ-Methyleneguanosine 5′-triphosphate (GMPPCP, GppCp) is a non-hydrolyzable analog of GTP used in a variety of applications that involve GTP binding including GTP-activation, GTP-inhibition, GTP transport, GTP hydrolysis and GTP structure stabilization. GMPPCP (GuoPP[CH2MP) is used to modulate and study G proteins involved in cell signaling, protein synthesis and other metabolic processes.
β,γ-Methyleneguanosine 5′-triphosphate sodium salt has been used as a GTP analog to complex with dynamin for cryo-electron microscopy studies. It has also been used to complex with Di-Ras1/Di-Ras2 and nucleotide exchange delivery studies.

Biochem/physiol Actions

βγ-Methyleneguanosine 5′-triphosphate (GMPPCP) is used in a variety of applications that involve GTP binding including GTP-activation, GTP-inhibition, GTP transport, GTP hydrolysis and GTP structure stabilization. GMPPCP is used to modulate and study G proteins involved in cell signaling, protein synthesis and other metabolic processes.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable


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Sandro F Ataide et al.
Science (New York, N.Y.), 331(6019), 881-886 (2011-02-19)
Cotranslational targeting of membrane and secretory proteins is mediated by the universally conserved signal recognition particle (SRP). Together with its receptor (SR), SRP mediates the guanine triphosphate (GTP)-dependent delivery of translating ribosomes bearing signal sequences to translocons on the target
Ravi Kiran Koripella et al.
Nature communications, 11(1), 3830-3830 (2020-08-02)
The mammalian mitochondrial ribosome (mitoribosome) and its associated translational factors have evolved to accommodate greater participation of proteins in mitochondrial translation. Here we present the 2.68-3.96 Å cryo-EM structures of the human 55S mitoribosome in complex with the human mitochondrial elongation
Zhu Li et al.
The Journal of biological chemistry, 292(10), 3977-3987 (2017-01-29)
IcmF is a 5'-deoxyadenosylcobalamin (AdoCbl)-dependent enzyme that catalyzes the carbon skeleton rearrangement of isobutyryl-CoA to butyryl-CoA. It is a bifunctional protein resulting from the fusion of a G-protein chaperone with GTPase activity and the cofactor- and substrate-binding mutase domains with
GTPase activity regulates kinase activity and cellular phenotypes of Parkinson's disease-associated LRRK2
Biosa A, et al.
Human Molecular Genetics, 22(6), 1140-1156 (2012)
Identification of the binding surface on Cdc42Hs for p21-activated kinase.
Guo W, Sutcliffe MJ, et al.
Biochemistry, 37, 14030-14037 (1988)

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