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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)

Quality Level

200

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

signalword

Warning

hcodes

H302

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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
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
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
Ricardo Soto-Rifo et al.
Nucleic acids research, 41(12), 6286-6299 (2013-05-01)
Here, we show a novel molecular mechanism promoted by the DEAD-box RNA helicase DDX3 for translation of the HIV-1 genomic RNA. This occurs through the adenosine triphosphate-dependent formation of a translation initiation complex that is assembled at the 5' m(7)GTP
La-related protein 1 (LARP1) binds the mRNA cap, blocking eIF4F assembly on TOP mRNAs
Lahr RM, et al.
eLife, 6, e24146-e24146 (2017)
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