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M3509 Sigma-Aldrich

β,γ-Methyleneguanosine 5′-triphosphate sodium salt

≥98% (HPLC)

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

  • CAS Number 10470-57-2

  • Empirical Formula (Hill Notation) C11H18N5O13P3 · xNa+

  • Molecular Weight 521.21 (free acid basis)

  •  MDL number MFCD00070117

  •  PubChem Substance ID 24896847

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Properties

Related Categories Biochemicals and Reagents, Nucleosides, Nucleotides, Oligonucleotides, Nucleotide Analogs More...
Quality Level   200
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

Description

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.

Packaging

25 mg in poly bottle

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.

Safety & Documentation

Safety Information

RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Protocols & Articles
Peer-Reviewed Papers
15

References

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