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Nucleic Acids Symposium Series 2006 50(1):53-54; doi:10.1093/nass/nrl027
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© 2006 Oxford University Press

Nucleotides and nucleic acids: A source of inspiration for the development of new, phosphorus-centered functional groups

Chrystel Lopin, Goulnara Garipova, Irina Kalinina, Pierre Raboisson, Tomohisa Osaki, Arnaud Gautier, Sébastien Balieu, Carmen Salcedo, Géraldine Gouhier and Serge R. Piettre

University of Rouen, Laboratoire des Fonctions Azotées et Oxygénées Complexes, UMR 6014 CNRS, IRCOF, rue Tesnières, F - 76821 - Mont Saint Aignan, France

Synthetic methodologies aiming at the creation of new phosphorus-centered functional groups are reported, as well as applications to the field of nucleotide chemistry. Thus, difluorophosphonothioate-based, ionic reagents 3b and 3d are shown to allow the stereocontrolled and efficient synthesis of phosphonodifluoromethyl analogues of nucleoside-3'-phosphates. An alternate, radical approach describes the use of hypophosphorous acid to stereoselectively link two furanosyl units in positions 3 and 5, and to provide an access to {alpha},{alpha}-difluoro-H-phosphinates. These intermediates are shown to be precursors to the corresponding fluorinated phosphonic acids, phosphonothioic acids and variously substituted phosphinates.


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