A new approach to the synthesis of branched and branched cyclic oligoribonucleotides.
The six-step synthesis of the di-triethylammonium salt of 5[prime]-O -trityl-6-N-pivaloyladenosine-2[prime]-(H -phosphonate)-3'-[(2-chlorophenyl) phosphate]9 from 3', 5'- O -(1,1,3,3-tetraisopropyldisiloxan-1,3-diyl)-6-N-pivaloyla denosine1in 68% overall yield is described. Compound9is converted into a branched pentaribonucleoside tetraphosphate 24 and a branched cyclic pentaribonucleotide ('lariat') 25 by solution phase triester chemistry involving both H-phosphonate and conventional phosphotriester coupling reactions. The monomeric building block 9 is proposed as a universal synthon for the preparation of branched and branched cyclic oligoribonucleotides derived from adenosine.
Reese
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CB
Department of Chemistry, King's College London, Strand, London WC2R 2LS, UK.
Song
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D000241:Adenosine; D002851:Chromatography, High Pressure Liquid; D009843:Oligoribonucleotides / Q000138:chemical synthesis* / Q000737:chemistry; D010710:Phosphates
D009843:Oligoribonucleotides; D010710:Phosphates; D000241:Adenosine