M5883

Sigma-Aldrich

7-Methylguanosine 5′-diphosphate sodium salt

≥92.5%

Synonym(s):
m7GDP
Empirical Formula (Hill Notation):
C11H17N5O11P2 · xNa+
CAS Number:
Molecular Weight:
457.23 (free acid basis)
MDL number:
PubChem Substance ID:
NACRES:
NA.51

Quality Level

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

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

Application

7-Methylguanosine 5′-diphosphate (m7GDP) may be used to study the structure, functions and metabolism of mRNA 5′-cap structures. M7GDP is used in the synthesis of mRNA cap analogues.

Packaging

10 mg in glass bottle
25 mg in poly bottle

storage_class_code

13 - Non 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

Magdalena Lewdorowicz et al.
RNA (New York, N.Y.), 10(9), 1469-1478 (2004-07-27)
Leishmania and other trypanosomatids are early eukaryotes that possess unusual molecular features, including polycistronic transcription and trans-splicing of pre-mRNAs. The spliced leader RNA (SL RNA) is joined to the 5' end of all mRNAs, thus donating a 5' cap that...
Laurent Volpon et al.
RNA (New York, N.Y.), 23(6), 927-937 (2017-03-23)
The eukaryotic translation initiation factor eIF4E acts in the nuclear export and translation of a subset of mRNAs. Both of these functions contribute to its oncogenic potential. While the biochemical mechanisms that underlie translation are relatively well understood, the molecular...
J Marcotrigiano et al.
Cell, 89(6), 951-961 (1997-06-13)
The X-ray structure of the eukaryotic translation initiation factor 4E (eIF4E), bound to 7-methyl-GDP, has been determined at 2.2 A resolution. eIF4E recognizes 5' 7-methyl-G(5')ppp(5')N mRNA caps during the rate-limiting initiation step of translation. The protein resembles a cupped hand...
A M McGuire et al.
Journal of biomolecular NMR, 12(1), 73-88 (1998-09-08)
The mRNA cap-binding protein eIF4E is the limiting factor in the eIF4F translation initiation complex, which mediates the binding of the 40S ribosome to the mRNA. 15N relaxation studies have been used to characterize the backbone dynamics of deuterated eIF4E...
Colin W Garvie
Analytical biochemistry, 434(1), 166-171 (2012-12-12)
The eukaryotic initiation factor 4E (eIF4E) is the key component of the translational initiation complex that recruits mRNA by binding to a unique "cap" structure located at the 5' end of the mRNA. Overexpression of eIF4E has been implicated in...

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