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mCAP
m7G(5')ppp(5')G Cap Analog, used to forming Cap 0 structure

Catalog No.B8174
Size Price Stock Qty
10ul (100 mM)
$55.00
In stock
50ul (100 mM)
$255.00
In stock
100ul (100 mM)
$437.00
In stock

Tel: +1-832-696-8203

Email: [email protected]

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Sample solution is provided at 25 µL, 10mM.

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Chemical structure

mCAP

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Chemical Properties

Cas No. N/A SDF Download SDF
Synonyms m7G(5')ppp(5')G Cap Analog, N7-Methyl-Guanosine-5'-Triphosphate-5'-Guanosine
Chemical Name N/A
Canonical SMILES OC1C(COP([O-])(OP([O-])(OP([O-])(OCC2OC(N3C=[N+](C)C4=C3N=C(N)NC4=O)C(O)C2O)=O)=O)=O)OC(N5C=NC6=C5N=C(N)NC6=O)C1O
Formula C21H30N10O18P3 (free acid) M.Wt 803.4 g/mol (free acid)
Solubility N/A Storage Store at -20°C or below
Shipping Condition Evaluation sample solution : ship with blue ice.All other available size: ship with RT , or blue ice upon request
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.

Research Update

1.Probst J, et al. Characterization of the ribonuclease activity on the skin surface. (2006) Genetic Vaccines and Therapy. 4(4).
2.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.
3.Furuichi Y, Shatkin AJ. Viral and cellular mRNA capping: past and prospects. Adv Virus Res. 2000;55:135-84.
4.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.
5.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.
6.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.
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.
8.Shuman S. Capping enzyme in eukaryotic mRNA synthesis. Prog Nucleic Acid Res Mol Biol. 1995;50:101-29.
8.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.
9.Konarska MM, Padgett RA, Sharp PA. Recognition of cap structure in splicing in vitro of mRNA precursors. (1984) Cell. 38(3):731-6.
10.Miura K. The cap structure in eukaryotic messenger RNA as a mark of a strand carrying protein information. (1981) Adv Biophys. 14:205-38.
11.Banerjee AK. 5'-terminal cap structure in eucaryotic messenger ribonucleic acids. (1980) Microbiol Rev. 44(2):175-205.
12.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.
13.Filipowicz W. Functions of the 5,-terminal m7G cap in eukaryotic mRNA. (1978) FEBS Lett. 96(1):1-11.
14.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.
15.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.

Background

mRNA of eucaryon and virus has a monomethylated cap structure, m7G(5')ppp(5')G or called mCAP, at the 5’-initiating terminal. The cap analog plays an important role in cellular processes, the initiation of protein synthesis, protecting RNA from exonuclease cleavage, uniquely recognition for recruiting protein factors for pre-mRNA splicing, polyadenylation and nuclear export. The cap could interact with different binding proteins, initiation factors and elements of ribosomes.

mCAP is the first cap analog for the molecular biology toolbox. MCAP inserts in the correct orientation to enhance translation with a 50% chance. The other 50% of molecules can’t be a substrate for efficient translation, reducing the specific activity of the transcript.

mCAP can be 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.

References:
[1].Abbas YM1, Laudenbach BT2, et al, Structure of human IFIT1 with capped RNA reveals adaptable mRNA binding and mechanisms for sensing N1 and N2 ribose 2'-O methylations. Proc Natl Acad Sci U S A. 2017 Mar 14;114(11):E2106-E2115.
[2].Katibah GE1, Qin Y2, et al, Broad and adaptable RNA structure recognition by the human interferon-induced tetratricopeptide repeat protein IFIT5. Proc Natl Acad Sci U S A. 2014 Aug 19;111(33):12025-30.
[3]. Kuge H1, Brownlee GG, et al, Cap ribose methylation of c-mos mRNA stimulates translation and oocyte maturation in Xenopus laevis. Nucleic Acids Res. 1998 Jul 1;26(13):3208-14.
[4]. Ramanathan A1, Robb GB1, et al, mRNA capping: biological functions and applications. Nucleic Acids Res. 2016 Sep 19;44(16):7511-26.
[5]. Probst J1, Brechtel S, et al, Characterization of the ribonuclease activity on the skin surface. Genet Vaccines Ther. 2006 May 29;4:4.
[6]. Karikó K1, Buckstein M, et al, Suppression of RNA recognition by Toll-like receptors: the impact of nucleoside modification and the evolutionary origin of RNA. Immunity. 2005 Aug;23(2):165-75.