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M6133

Sigma-Aldrich

7-Methylguanosine 5′-triphosphate sodium salt

≥85% (HPLC)

Synonym(s):

m7GTP

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About This Item

Empirical Formula (Hill Notation):
C11H18N5O14P3 · xNa+
CAS Number:
104809-18-9
Molecular Weight:
537.21 (free acid basis)
MDL number:
MFCD00063376
UNSPSC Code:
41106305
PubChem Substance ID:
24897079
NACRES:
NA.51

biological source

natural (inorganic)

Assay

≥85% (HPLC)

form

powder

storage temp.

−20°C

SMILES string

[Na+].C[n+]1cn([C@@H]2O[C@H](COP(O)(=O)OP(O)(=O)OP(O)([O-])=O)[C@@H](O)[C@H]2O)c3N=C(N)NC([O-])c13

InChI

1S/C11H20N5O14P3.Na/c1-15-3-16(8-5(15)9(19)14-11(12)13-8)10-7(18)6(17)4(28-10)2-27-32(23,24)30-33(25,26)29-31(20,21)22;/h3-4,6-7,9-10,17-18H,2H2,1H3,(H,23,24)(H,25,26)(H3,12,13,14)(H2,20,21,22);/q;+1/p-1/t4-,6-,7-,9?,10-;/m1./s1

InChI key

FSMRTZAMTMQMEF-OCMBMSOASA-M

Related Categories

General description

7-Methylguanosine 5′-triphosphate is a mRNA cap structural analog.

Application

7-Methylguanosine 5′-triphosphate (m7GTP) is use to study the structures and mechanisms of eukaryotic cellular mRNA caps in the context of mRNA involvement in protein synthesis. m7GTP may be used to create affinity media for capture and purification of molecules such as eukaryotic initiation factor eIF4E.
7-Methylguanosine 5′-triphosphate sodium salt has been used to test its affinity towards Poly(A)-specific ribonuclease (PARN) polypeptides using fluorescence titrations. It has also been used in crystallization along with gemin5 fragment (G5N) and DM15 region of human La-related 15 protein 1 ( LARP1).

Biochem/physiol Actions

7-Methylguanosine 5′-triphosphate (m7GTP) inhibits in vitro protein synthesis by binding to translation initiation complexes. m7GTP is useful to study the structures and mechanisms of eukaryotic cellular mRNA caps in the context of mRNA involvement in protein synthesis. m7GTP has a high affinity for eukaryotic initiation factor eIF4E and may be used to create affinity media for their capture and purification.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Regina Cencic et al.
Analytical biochemistry, 560, 24-29 (2018-09-09)
All cellular cytoplasmic mRNAs are capped at their 5' ends with an m7GpppN group. Several proteins that mediate cap function have been identified by cap affinity purification, enabling their characterization in a number of biological processes. Among these, eukaryotic initiation
Ya-Jun Wang et al.
PloS one, 7(9), e44079-e44079 (2012-09-08)
Influenza virus, which spreads around the world in seasonal epidemics and leads to large numbers of deaths every year, has several ribonucleoproteins in the central core of the viral particle. These viral ribonucleoproteins can specifically bind the conserved 3' and
Yih-Leh Huang et al.
The Journal of biological chemistry, 280(13), 13153-13162 (2005-01-29)
The S-adenosylmethionine-dependent guanylyltransferase of bamboo mosaic virus belongs to a novel class of mRNA capping enzymes distantly conserved in Alphavirus-like superfamily. The reaction sequence of the viral enzyme has been proposed comprising steps of 1) binding of GTP and S-adenosylmethionine
Thomas Monecke et al.
Nucleic acids research, 37(12), 3865-3877 (2009-04-24)
The 5'-cap of spliceosomal small nuclear RNAs, some small nucleolar RNAs and of telomerase RNA was found to be hypermethylated in vivo. The Trimethylguanosine Synthase 1 (TGS1) mediates this conversion of the 7-methylguanosine-cap to the 2,2,7-trimethylguanosine (m(3)G)-cap during maturation of
Susan Parrish et al.
Proceedings of the National Academy of Sciences of the United States of America, 104(7), 2139-2144 (2007-02-07)
Previous studies indicated that the vaccinia virus D10 protein, which is conserved in all sequenced poxviruses, participates in the rapid turnover of host and viral mRNAs. D10 contains a motif present in the family of Nudix/MutT enzymes, a subset of
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