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M3509

β,γ-Methyleneguanosine 5′-triphosphate sodium salt

≥98% (HPLC), synthetic (organic), powder

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C11H18N5O13P3 · xNa+
CAS Number:
10470-57-2
Molecular Weight:
521.21 (free acid basis)
UNSPSC Code:
41106305
PubChem Substance ID:
24896847
NACRES:
NA.51
MDL number:
MFCD00070117
Assay:
≥98% (HPLC)
Biological source:
synthetic (organic)
Form:
powder
Solubility:
water: 50 mg/mL, clear, colorless
Storage temp.:
−20°C
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Product Name

β,γ-Methyleneguanosine 5′-triphosphate sodium salt, ≥98% (HPLC)

biological source

synthetic (organic)

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

General description

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

Application

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.
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.

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

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000495837
0000495837
SLCH4556
0000375577
0000324650

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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
View All Related Papers

Global Trade Item Number

SKUGTIN
M3509-25MG04061834050278