Synthesis and incorporation into DNA fragments of the artificial nucleobase, 2-amino-8-oxopurine

Claudio Cadena-Amaro; Muriel Delepierre; Sylvie Pochet

doi:10.1016/j.bmcl.2004.12.021

Synthesis and incorporation into DNA fragments of the artificial nucleobase, 2-amino-8-oxopurine

Bioorg Med Chem Lett. 2005 Feb 15;15(4):1069-73. doi: 10.1016/j.bmcl.2004.12.021.

Authors

Claudio Cadena-Amaro¹, Muriel Delepierre, Sylvie Pochet

Affiliation

¹ Unité de Chimie Organique, URA CNRS 2128, Institut Pasteur, 28, rue du Docteur Roux, 75724 Paris cedex 15, France.

PMID: 15686914
DOI: 10.1016/j.bmcl.2004.12.021

Abstract

The nucleoside 2-amino-9-(2-deoxy-beta-d-ribofuranosyl)-7,8-dihydro-8-oxo-purine (dJ) was obtained in eight steps from 2'-deoxyguanosine. The appropriate protected phosphoramidite was synthesized and incorporated into DNA oligonucleotides. The thermal stability of heteroduplexes containing 2-amino-8-oxopurine (J) was investigated by UV-thermal denaturation experiments. The results obtained can be interpreted by the base pairing schemes involving the two edges of dJ depending on the anti and syn orientations.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Base Pairing
Nucleic Acid Denaturation
Oligodeoxyribonucleotides / chemical synthesis*
Oligodeoxyribonucleotides / chemistry
Organophosphorus Compounds
Purinones / chemical synthesis*
Purinones / chemistry
Temperature

Substances

Oligodeoxyribonucleotides
Organophosphorus Compounds
Purinones
phosphoramidite