4395-48-6Relevant articles and documents
Chemical synthesis of a 5′-terminal TMG-capped triribonucleotide m32,2,7G5′ pppAmpUmpA of U1 RNA
Sekine, Mitsuo,Kadokura, Michinori,Satoh, Takahiko,Seio, Kohji,Wada, Takeshi,Fischer, Utz,Sumpter, Vicki,Lührmann, Reinhard
, p. 4412 - 4422 (2007/10/03)
The 5′-terminal TMG-capped triribonucleotide, m32,2,7G5′pppAmpUmpA, has been synthesized by condensation of an appropriately protected triribonucleotide derivative of ppAmpUmpA with a new TMG-capping reagent. During this total synthesis, it was found that the regioselective 2′-O-methylation of 3′,5′-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-N-(4- monomethoxytrityl)adenosine was achieved by use of MeI/Ag2O without affecting the base moiety. A new route to 2-N,2-N-dimethylguanosine from guanosine via a three-step reaction has also been developed by reductive methylation using paraformaldehyde and sodium cyanoborohydride. These key intermediates were used as starting materials for the construction of a fully protected derivative of pAmpUmpA and a TMG-capping reagent of Im-pm32,2,7G. The target TMG-capped tetramer, m32,2,7G5′ pppAmpUmpA, was synthesized by condensation of a partially protected triribonucleotide 5′-terminal diphosphate species, ppAMMTrmpUmpA, with Im-pm32,2,7G followed by treatment with 80% acetic acid. The structure of m32,2,7G5′ pppAmpUmpA was characterized by 1H and 31P NMR spectroscopy as well as enzymatic assay using snake venom phosphodiesterase, calf intestinal phosphatase, and nuclease P1.
