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M3509

Sigma-Aldrich

β,γ-Methyleneguanosine 5′-triphosphate sodium salt

≥98% (HPLC)

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Synonym(s):
GMPPCP, GppCp, Guanosine-5′-[(β,γ)-methyleno]triphosphate sodium salt
Empirical Formula (Hill Notation):
C11H18N5O13P3 · xNa+
CAS Number:
Molecular Weight:
521.21 (free acid basis)
MDL number:
PubChem Substance ID:

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

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This Item
G0635G6129G8634
assay

≥98% (HPLC)

assay

≥85% (HPLC)

assay

≥99% (HPLC)

assay

≥90% (contains < 10% GDP, HPLC)

form

powder

form

powder

form

powder

form

powder

solubility

water: 50 mg/mL, clear, colorless

solubility

H2O: 50 mg/mL

solubility

H2O: 50 mg/mL

solubility

H2O: ≥75 mg/mL (Solutions are very unstable; prepare immediately prior to use.)

storage temp.

−20°C

storage temp.

−70°C

storage temp.

−20°C

storage temp.

−20°C

Quality Level

200

Quality Level

200

Quality Level

200

Quality Level

200

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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


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Structural inhibition of dynamin-mediated membrane fission by endophilin
Hohendahl A, et al.
eLife, 6, e26856-e26856 (2017)
T Schweins et al.
Journal of molecular biology, 266(4), 847-856 (1997-03-07)
GTP and ATP hydrolysing proteins have an absolute requirement for a divalent cation, which is usually Mg2+, as a cofactor in the enzymatic reaction. Other phosphoryl transfer enzymes employ more than one divalent ion for the enzymatic reaction. It is
Gilles Labesse et al.
Nucleic acids research, 39(8), 3458-3472 (2010-12-15)
Nucleoside Monophosphate Kinases (NMPKs) family are key enzymes in nucleotide metabolism. Bacterial UMPKs depart from the main superfamily of NMPKs. Having no eukaryotic counterparts they represent attractive therapeutic targets. They are regulated by GTP and UTP, while showing different mechanisms
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

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