1093268-63-3
Chemical Structure
β-S-ARCA
Synonym(s): 3'-O-Me-m7G(5')ppp(5')G
- CAS No.: 1093268-63-3
- Formula:C22H31N10O17P3S
- Molecular Weight:832.52
IUPAC Name: pentanoic-2,2-d2 acid
InChIKey: DOOBEITVZIIXPE-XJGHKLLTSA-N
SMILES: O=P(O)(OC[C@@H]1[C@@H](O)[C@@H](O)[C@H](N2C=NC3=C2NC(N)=NC3=O)O1)OP(OP(OC[C@@H]4[C@@H](O)[C@@H](OC)[C@H](N5C(NC(N)=N6)=C([N+](C)=C5)C6=O)O4)([O-])=O)(S)=O
Biological Activity: β-S-ARCA (3'-O-Me-m7G(5')ppp(5')G) is a mRNA 7-methylguanosine (m7G) cap analog carrying a phosphorothioate (PS) moiety. β-S-ARCA binds eIF4E via electrostatic interactions between its β-sulfur atom and positively charged Arg and Lys residues in the protein binding site. β-S-ARCA prevents the decapping by Dcp2, increases the mRNA half-life, enhances cap-dependent translation, and increases protein expression in cells. β-S-ARCA has been applied in researching experimental mRNA-based anticancer vaccines[1][2].
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β-S-ARCA | β-S-ARCA (3'-O-Me-m7G(5')ppp(5')G) is a mRNA 7-methylguanosine (m7G) cap analog carrying a phosphorothioate (PS) moiety. β-S-ARCA binds eIF4E via electrostatic interactions between its β-sulfur atom and positively charged Arg and Lys residues in the protein binding site. β-S-ARCA prevents the decapping by Dcp2, increases the mRNA half-life, enhances cap-dependent translation, and increases protein expression in cells. β-S-ARCA has been applied in researching experimental mRNA-based anticancer vaccines. | |||||||||||||||||||||
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- [1]. Warminski M, et al. Chemical Modifications of mRNA Ends for Therapeutic Applications. Acc Chem Res. 2023;56(20):2814-2826. [Content Brief]
- [2]. Wojtczak BA, et al. 5'-Phosphorothiolate Dinucleotide Cap Analogues: Reagents for Messenger RNA Modification and Potent Small-Molecular Inhibitors of Decapping Enzymes. J Am Chem Soc. 2018;140(18):5987-5999. [Content Brief]
Keywords
