Efficient incorporation of 1-(2-deoxy-beta-D-ribofuranosyl)-2-oxo-imidazole-4-carboxamide into DNA via a suitable convertible phosphoramidite derivative

Claudio Cadena-Amaro (1) , Sylvie Pochet (1)

1 Chimie Organique

The synthetic scheme of 1-(2-deoxy-beta-D-ribofuranosyl)-2-oxo-imidazole-4-carboxamide (3) is based on the ring contraction of pyrimidine (5-BrdU) into imidazolin-2-one. The rearrangement leads to the unexpected Mixture of the deoxynucleoside 4 beta and its alpha anomer. The mechanism of the anomerisation under basic conditions is proposed. Further conversion of 4-carboxylic acid into amide affords the title compound 3. The conversion of 4-carboxylic acid into ethyl ester is preferred for the preparation of the phosphoramidite derivative 11 suitable for chemical incorporation of the modified nucleobase into DNA. Thermal denaturation studies show that 2-oxoY within the sequence used pairs more favorably with the purines than the pyrimidines.

Domains: Life Sciences [q-bio]; Microbiology and Parasitology

Claudio Cadena-Amaro, Sylvie Pochet. Efficient incorporation of 1-(2-deoxy-beta-D-ribofuranosyl)-2-oxo-imidazole-4-carboxamide into DNA via a suitable convertible phosphoramidite derivative. Tetrahedron, 2005, 61 (21), pp.5081-5087. ⟨10.1016/j.tet.2005.03.040⟩. ⟨pasteur-00166585⟩