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M3509

Sigma-Aldrich

β,γ-Methyleneguanosine 5′-triphosphate sodium salt

≥98% (HPLC)

Sinônimo(s):

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

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About This Item

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

fonte biológica

synthetic (organic)

Nível de qualidade

Ensaio

≥98% (HPLC)

Formulário

powder

solubilidade

water: 50 mg/mL, clear, colorless

temperatura de armazenamento

−20°C

cadeia de caracteres SMILES

[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);;

chave InChI

LJQPGKRRFLMZPX-UHFFFAOYSA-N

Descrição geral

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

Aplicação

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.

Ações bioquímicas/fisiológicas

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.

Código de classe de armazenamento

11 - Combustible Solids

Classe de risco de água (WGK)

WGK 3

Ponto de fulgor (°F)

Not applicable

Ponto de fulgor (°C)

Not applicable


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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)
Dielle E Whitecross et al.
Scientific reports, 7(1), 16194-16194 (2017-11-25)
Rab5 is a small monomeric GTPase that mediates protein trafficking during endocytosis. Inactivation of Rab5 by GTP hydrolysis causes a conformational change that masks binding sites on its "switch regions" from downstream effectors. The p85 subunit of phosphatidylinositol 3-kinase (PI3K)
Identification of the binding surface on Cdc42Hs for p21-activated kinase.
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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

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