Skip to Content
MilliporeSigma
All Photos(2)

Key Documents

View All Documentation

M3509

Sigma-Aldrich

β,γ-Methyleneguanosine 5′-triphosphate sodium salt

≥98% (HPLC)

Synonym(s):

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

Sign Into View Organizational & Contract Pricing

Select a Size

25 MG
$256.70

$256.70

List Price$302.00Save 15%
Web-Only Promotion

Available to ship onMay 01, 2025Details

All Photos(2)

Select a Size

Change View
25 MG
$256.70

About This Item

Empirical Formula (Hill Notation):
C11H18N5O13P3 · xNa+
CAS Number:
10470-57-2
Molecular Weight:
521.21 (free acid basis)
MDL number:
MFCD00070117
UNSPSC Code:
41106305
PubChem Substance ID:
24896847
NACRES:
NA.51

$256.70

List Price$302.00Save 15%
Web-Only Promotion

Available to ship onMay 01, 2025Details

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

Related Categories

General description

βγ-Methyleneguanosine 5′-triphosphate (GMPPCP, GppCp) is a non-hydrolyzable analog of GTP.[1]

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.[2] It has also been used to complex with Di-Ras1/Di-Ras2 and nucleotide exchange delivery studies.[3]

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

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
SLCH4556
SLCH4556
0000375577
0000375577
0000324650

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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
Joseph Gawronski-Salerno et al.
Journal of structural biology, 158(1), 122-128 (2006-12-23)
Ffh and FtsY are GTPase components of the signal recognition particle co-translational targeting complex that assemble during the SRP cycle to form a GTP-dependent and pseudo twofold symmetric heterodimer. Previously the SRP GTPase heterodimer has been stabilized and purified for
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)
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
View All Related Papers

Questions

Reviews

No rating value

Active Filters

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service