Synthesis of nucleosides containing a photolabile 2-(2-nitrophenyl)propoxycarbonyl group

Abstract

At present, DNA biochips are widely used in medicine as diagnostic systems [1, 2]. Oligonucleotide biochips are often obtained with the aid of photolabile protecting groups [3–7]. The latter should be stable under the conditions of oligonucleotide synthesis but should be readily removed by photolysis without involving the protected moiety. A widely used photolabile protecting group is the o-nitrobenzyl group [3, 8–10]. The goal of the present work was to extend the series of nucleosides protected by the photolabile 2-(2-nitrophenyl)propoxycarbonyl group and containing readily removable protecting groups in the aromatic heteroring, which can subsequently be used in the design of oligonucleotide biochips. We have synthesized previously unknown nucleosides 4–7. Compounds 4 and 5 were obtained by acylation of 2′-deoxyguanosine and 2′-deoxyadenosine with phenoxyacetyl chlorides 1 and 2, respectively. Nucleosides 6 and 7 protected by photolabile 2-(2-nitrophenyl)propoxycarbonyl groups were synthesized by treatment of compounds 4 and 5, respectively, with 2-(2-nitrophenyl)propyl chloroformate (3) which was prepared as described in [10]. Compounds 6 and 7 were isolated as mixtures of diastereoisomers. ISSN 1070-4280, Russian Journal of Organic Chemistry, 2015, Vol. 51, No. 1, pp. 141–144. © Pleiades Publishing, Ltd., 2015. Original Russian Text © E.B. Nikolaenkova, I.A. Os’kina, V.A. Savel’ev, A.Ya. Tikhonov, V.A. Ryabinin, A.N. Sinyakov, 2015, published in Zhurnal Organicheskoi Khimii, 2015, Vol. 51, No. 1, pp. 142–144.