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

Abstract : 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.
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https://hal-pasteur.archives-ouvertes.fr/pasteur-00166585
Contributor : Sylvie Pochet <>
Submitted on : Tuesday, August 7, 2007 - 2:37:24 PM
Last modification on : Monday, January 13, 2020 - 5:08:05 PM

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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, Elsevier, 2005, 61 (21), pp.5081-5087. ⟨10.1016/j.tet.2005.03.040⟩. ⟨pasteur-00166585⟩

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