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Nucleic Acids Research, Vol 27, Issue 13 2672-2681, Copyright © 1999 by Oxford University Press

ARTICLES

A new approach to the synthesis of branched and branched cyclic oligoribonucleotides

CB Reese and Q Song
Department of Chemistry, King's College London, Strand, London WC2R 2LS, UK.

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.
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