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G8877

Sigma-Aldrich

Guanosine 5′-triphosphate sodium salt hydrate

≥95% (HPLC), powder

Synonym(s):
GTP
Empirical Formula (Hill Notation):
C10H16N5O14P3 · xNa+
CAS Number:
Molecular Weight:
523.18 (free acid basis)
Beilstein:
3585677
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.77

Quality Level

assay

≥95% (HPLC)

form

powder

color

white

solubility

H2O: 50 mg/mL

shipped in

dry ice

storage temp.

−20°C

SMILES string

[Na+].[Na+].[Na+].NC1=Nc2c(ncn2[C@@H]3O[C@H](COP(O)(=O)OP([O-])(=O)OP([O-])([O-])=O)[C@@H](O)[C@H]3O)C(=O)N1

InChI

1S/C10H16N5O14P3.3Na/c11-10-13-7-4(8(18)14-10)12-2-15(7)9-6(17)5(16)3(27-9)1-26-31(22,23)29-32(24,25)28-30(19,20)21;;;/h2-3,5-6,9,16-17H,1H2,(H,22,23)(H,24,25)(H2,19,20,21)(H3,11,13,14,18);;;/q;3*+1/p-3/t3-,5-,6-,9-;;;/m1.../s1

InChI key

KZRMTEVIDYXWQW-CYCLDIHTSA-K

Gene Information

human ... HRAS(3265)

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Application

Guanosine 5′-triphosphate sodium salt hydrate has been used:
  • in the preparation of horseradish peroxidase (HRP)-modified platination reagents
  • in whole cell, voltage-clamp recordings
  • in in vitro inhibition of transglutaminase (tTG)

Packaging

10, 25, 100, 250 mg in poly bottle
1 g in poly bottle

Biochem/physiol Actions

GTP functions as a carrier of phosphates and pyrophosphates involved in channeling chemical energy into specific biosynthetic pathways. GTP activates the signal transducing G proteins which are involved in various cellular processes including proliferation, differentiation, and activation of several intracellular kinase cascades. Proliferation and apoptosis are regulated in part by the hydrolysis of GTP by small GTPases Ras and Rho. Another type of small GTPase, Rab, plays a role in the docking and fusion of vesicles and may also be involved in vesicle formation. In addition to its role in signal transduction, GTP also serves as an energy-rich precursor of mononucleotide units in the enzymatic biosynthesis of DNA and RNA.

Features and Benefits

This compound is a featured product for Cyclic Nucleotide research. Click here to discover more featured Cyclic Nucleotide products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

Preparation Note

Prepared by enzymatic phosphorylation of 5′-GMP.

Storage Class Code

11 - Combustible Solids

WGK Germany

WGK 3

Flash Point F

Not applicable

Flash Point C

Not applicable

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

Flufenamic acid affects multiple currents and causes intracellular Ca2+ release in Aplysia bag cell neurons
Gardam K E, et al.
Journal of Neurophysiology, 100(1), 38-49 (2008)
T cells from celiac disease lesions recognize gliadin epitopes deamidated in situ by endogenous tissue transglutaminase
Molberg O, et al.
European Journal of Immunology, 31(5), 1317-1323 (2001)
Feng Rao et al.
Analytical biochemistry, 389(2), 138-142 (2009-03-31)
The cyclic dinucleotide c-di-GMP is a widespread bacterial messenger molecule with potential application as a therapeutic agent for treating bacterial infection. Current enzymatic synthesis of c-di-GMP using mesophilic diguanylate cyclase (DGC) proteins suffers from low production yield due to protein...
Rob P M van Gijlswijk et al.
Clinical chemistry, 48(8), 1352-1359 (2002-07-27)
Microarray platforms will change immunochemical and nucleic acid-based analysis of cell homogenates and body fluids compared with classic analyses. Microarrays use labeled target and immobilized probes, rather than fixed targets and labeled probes. We describe a method for simultaneous labeling...
Benjamin Judkewitz et al.
Nature protocols, 4(6), 862-869 (2009-05-16)
In order to link our knowledge of single neurons with theories of network function, it has been a long-standing goal to manipulate the activity and gene expression of identified subsets of mammalian neurons within the intact brain in vivo. This...

Protocols

LC MS Analysis of Nucleotides Effect of pH

ZIC-cHILIC is a densely bonded zwitterionic stationary phase with phosphorylcholine functional groups covalently attached to silica.

HPLC Analysis of GMP, GDP and GTP on SeQuant ZIC-HILIC

HPLC Analysis of GMP, GDP and GTP on SeQuant ZIC-HILIC

LC/MS Analysis of Nucleotides on SeQuant ZIC-cHILIC

HILIC separation is an alternative that permits sensitive MS detection and without the use of ion-pair reagents.

Related Content

Discover Bioactive Small Molecules for Cyclic Nucleotides

Cyclic nucleotides, including cyclic AMP (cAMP), cyclic GMP (cGMP) and cyclic ADP-ribose, have been extensively studied as second messengers of intracellular events initiated by activation of GPCRs. cAMP modifies cell function in all eukaryotic cells, principally through the activation of cAMP-dependent protein kinase (PKA), but also through cAMP-gated ion channels and guanine nucleotide exchange factors directly activated by cAMP.

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