DIPENTAFLUOROPHENYL CARBONATE - A REAGENT FOR THE SYNTHESIS OF OLIGONUCLEOTIDES AND THEIR CONJUGATES

Dipentafluorophenyl carbonate has been successfully used as condensing agent for the internucleotide bond formation in the synthesis of olig onucleotides via H-phosphonate approach. The mechanism of a nucleotide component activation with this reagent has been investigated with the help of P-31 NMR spectroscopy. It was shown that preactivation of deo xynucleoside H-phosphonate with dipentafluorophenyl carbonate has no i nfluence on the efficiency of the synthesis. This reagent is highly re active, nonhygroscopic and stable on storage at room temperature. The effectiveness of dipentafluorophenyl carbonate in the oligonucleotide chemistry has been demonstrated in the solid-phase synthesis of 10-50- mers on 0.2, 1 and 10 mumol scales. The use of this reagent for the de rivatisation of polymer supports as well as for the synthesis of oligo nucleotide conjugates with polyethylene glycol and a lipid is describe d.