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- W2049857490 abstract "Convergent synthesis of cyclic branched tetraribonucleotide 9, modelling the lariat of pre-mRNA processing reaction (Splicing), is reported. The first key step in the present strategy involves the condensation of the appropriately protected 5′-O-levulinyl-G3′p5′ U3′ phosphodiester block 4 with the 3′, 5′-dihydroxy-6-N-benzoyl-2′-O-pixyl(9-phenylxanthen-9-yl) adenosine 5,in presence of an activating agent, to give 6a (53%). Chemospecific phosphorylation of 3′-OH of 6a afforded the intermediate 6b (88%) which was treated with mid acid to achieve a regiospecific removal of the 2′-O-pixyl group to give compound 6c (99%). The second key step involved the introduction of biscyanoethylphosphotriester moiety to the 2′-OH of the branch-point adenosine in 6c, in one single step using (biscyanoethoxy)-(diisopropylamino)phosphine to give the crucial branch-point building block 6d (68%), with two dissimilar vicinal phosphates at 2′- and 3′-of the branch-point, 6d was then condensed with N-4-benzoyl-2′,3′-di-O-acetylcytidine then specifically removed from 7a by hydrazine hydrate to give the intermediate 7b (83%) which was subsequently treated with a bulky tertiary amine to give the branch-point-2′-cyanoethylphosphodiester block 7c (74%). A unique intramolecular 5′ → 2′ cyclization was then brought about in 7c by treatment with an activating agent under a high dilution condition to afford the fully protected cyclic branched tetramer 8 (61%). This oligomer was then deprotected in the usual manner and purified to give the cyclic branched tetramer 9 in 30% isolated yield, the first synthetic lariat known to date. Detailed 500 MHz 1H-NMR and 202.4 MHz 31P-NMR studies on 9 have unequivocally established its purity. Detailed spectroscopic studies such as COSY, HOHAHA, ROESY & 31P-1H-NMR shift correlation spectroscopy have clearly established the structural integrity of the tetrameric lariat RNA." @default.
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- W2049857490 date "1991-11-01" @default.
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- W2049857490 title "Synthesis of tetrameric cyclic branched-RNA (lariat) modelling the introns of group II and nuclear pre-mRNA processing reaction (splicing)" @default.
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- W2049857490 doi "https://doi.org/10.1016/s0040-4020(01)91031-2" @default.
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