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Merck

M5883

7-Methylguanosine 5′-diphosphate sodium salt

≥92.5%, synthetic (organic), powder

Synonym(s):

7-Methyl-gdp, m7GDP

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About This Item

Empirical Formula (Hill Notation):
C11H17N5O11P2 · xNa+
CAS Number:
Molecular Weight:
457.23 (free acid basis)
UNSPSC Code:
41106305
PubChem Substance ID:
NACRES:
NA.51
MDL number:

Product Name

7-Methylguanosine 5′-diphosphate sodium salt, ≥92.5%

SMILES string

[Na+].[Na+].C[n+]1cn([C@@H]2O[C@H](COP([O-])(=O)OP(O)([O-])=O)[C@@H](O)[C@H]2O)c3nc(N)nc([O-])c13

InChI

1S/C11H17N5O11P2.2Na/c1-15-3-16(8-5(15)9(19)14-11(12)13-8)10-7(18)6(17)4(26-10)2-25-29(23,24)27-28(20,21)22;;/h3-4,6-7,10,17-18H,2H2,1H3,(H5-,12,13,14,19,20,21,22,23,24);;/q;2*+1/p-2/t4-,6-,7-,10-;;/m1../s1

InChI key

VSMXIKIFPKDZJA-IDIVVRGQSA-L

biological source

synthetic (organic)

assay

≥92.5%

form

powder

solubility

water: 50 mg/mL, clear to very slightly hazy, colorless to very faintly yellow

storage temp.

−20°C

Quality Level

Application

7-Methylguanosine 5′-diphosphate sodium salt has been used as a component of the elution buffer for the purification of 5’capped RNA.

General description

7-Methylguanosine 5′-diphosphate (m7GDP) is derived when the human decapping Dcp2 enzyme cleaves the cap of the deadenylated mRNAs during the 5′–3′ mRNA decay pathway.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


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DcpS can act in the 5??3? mRNA decay pathway in addition to the 3??5? pathway
Erwin VD, et al.
Proceedings of the National Academy of Sciences, 100(21) (2003)
H Matsuo et al.
Nature structural biology, 4(9), 717-724 (1997-09-26)
eIF4E, the mRNA cap binding protein, is a master switch that controls eukaryotic translation. To be active, it must bind eIF4G and form the eIF4F complex, which also contains eIF4A. Translation is downregulated by association of eIF4E with 4E-BP, which
7-methylguanosine diphosphate (m7GDP) is not hydrolyzed but strongly bound by Decapping Scavenger (DcpS) enzymes and potently inhibits their activity
Wypijewska A, et al.
Biochemistry, 51(40) (2012)
A B Sachs et al.
Nature structural biology, 7(5), 356-361 (2000-05-10)
The eukaryotic cap and poly(A) tail binding proteins, eIF4E and Pab1p, play important roles in the initiation of protein synthesis. The recent structures of the complex of eIF4E bound to the methylated guanosine (cap) found at the 5'end of messenger
Susan Parrish et al.
Journal of virology, 81(23), 12973-12978 (2007-09-21)
Vaccinia virus (VACV) encodes enzymes that cap the 5' end of viral mRNAs, which enhances their stability and translation. Nevertheless, recent studies demonstrated that the VACV D10 protein (VACV-WR_115) decaps mRNA, an enzymatic activity not previously shown to be encoded

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