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You are at: All > Nucleotides > Nucleotides by Structural Class > 5'-5' Dinucleoside Triphosphates (Cap Analogs)

N-7001
mCAP
m7G(5')ppp(5')G Cap Analog, N7-Methyl-Guanosine-5'-Triphosphate-5'-Guanosine

mCAP

Extinction Coefficient: 21,000 Lmol-1cm-1 at 254 nm
Molecular Weight: 803.4 g/mol (free acid)
Molecular Formula: C21H30N10O18P3 (free acid)
Salt Form: NH4+
Purity Specification: ≥90% by AX-HPLC

Shipped at 100 mM in H2O.
1 µmole: 10 µL
5 µmole: 50 µL
10 µmole: 100 µL
250 mg


Certificate(s) of Analysis
T1-BFK01A-5

 
Eukaryotic and viral messenger RNA (mRNA) has a monomethylated cap structure, m7G(5')ppp(5')G or mCAP, at the 5’-terminus. The cap analog plays an important role in cellular processes, most notably the initiation of mRNA translation. The cap interacts with different binding proteins, initiation factors and elements of ribosomes.
 
mCAP was the first cap analog to be introduced to the molecular biology toolbox. Half of the time, mCAP inserts in the correct orientation to enhance translation. The other 50% of molecules are not substrates for efficient translation, reducing the specific activity of the transcript. More recently, Anti Reverse Cap Analog (ARCA) was introduced. ARCA can only insert in the proper orientation, resulting in mRNAs that are translated twice as efficiently as those initiated with mCAP.
 
mCAP is incorporated in a transcription by including a mixture of the cap analog and GTP (usually at a 4:1 ratio). Approximately 80% of synthesized mRNA will possess a 5’ cap, while the remaining 20% will possess a 5’ triphosphate.



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Reference(s)
Probst J, et al. Characterization of the ribonuclease activity on the skin surface. (2006) Genetic Vaccines and Therapy. 4(4).
Kariko, K., Buckstein, M., Ni, H. & Weissman, D. Suppression of RNA Recognition by Toll-like Receptors: The Impact of Nucleoside Modifiation and the Evolutionary Origin of RNA (2005). Immunity, 23(2), 165-175.
Furuichi Y, Shatkin AJ. Viral and cellular mRNA capping: past and prospects. Adv Virus Res. 2000;55:135-84.
Matsuo H, Moriguchi T, Takagi T, Kusakabe T, Buratowski S, Sekine M, Kyogoku Y, Wagner G. Efficient Synthesis of 13C, 15N-Labeled RNA Containing the Cap Structure m7GpppA. J. Am. Chem. Soc., 2000;122(11):2417–2421.
Ro-Choi TS. Nuclear snRNA and nuclear function (discovery of 5' cap structures in RNA). Crit Rev Eukaryot Gene Expr. 1999;9(2):107-58.
Hodel AE, Gershon PD, Quiocho FA. Structural basis for sequence-nonspecific recognition of 5'-capped mRNA by a cap-modifying enzyme. Mol Cell. 1998 Feb;1(3):443-7.
Hodel AE, Gershon PD, Shi X, Wang SM, Quiocho FA. Specific protein recognition of an mRNA cap through its alkylated base. Nat Struct Biol. 1997 May;4(5):350-4.
Shuman S. Capping enzyme in eukaryotic mRNA synthesis. Prog Nucleic Acid Res Mol Biol. 1995;50:101-29.
Ahola T, Kaariainen L. Reaction in alphavirus mRNA capping: formation of a covalent complex of nonstructural protein nsP1 with 7-methyl-GMP. (1995) Proc Natl Acad Sci U S A, 92(2): 507-11.
Konarska MM, Padgett RA, Sharp PA. Recognition of cap structure in splicing in vitro of mRNA precursors. (1984) Cell. 38(3):731-6.
Miura K. The cap structure in eukaryotic messenger RNA as a mark of a strand carrying protein information. (1981) Adv Biophys. 14:205-38.
Banerjee AK. 5'-terminal cap structure in eucaryotic messenger ribonucleic acids. (1980) Microbiol Rev. 44(2):175-205.
Rosenberg M, Paterson BM. Efficient cap-dependent translation of polycistronic prokaryotic mRNAs is restricted to the first gene in the operon. (1979) Nature. 21;279(5715):696-701.
Filipowicz W. Functions of the 5,-terminal m7G cap in eukaryotic mRNA. (1978) FEBS Lett. 96(1):1-11.
Zan-Kowalczewska M, Bretner M, Sierakowska H, Szczesna E, Filipowicz W, Shatkin AJ. Removal of 5'-terminal m7G from eukaryotic mRNAs by potato nucleotide pyrophosphatase and its effect on translation. (1977) Nucleic Acids Res. 4(9):3065-81.
Furuichi Y, Miura K. A blocked structure at the 5' terminus of mRNA from cytoplasmic polyhedrosis virus. Nature. 1975 Jan 31;253(5490):374-5.


 

 


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