Molecules 2005, 10(9), 1048-1073; doi:10.3390/10091048
Article

The Preparation of New Phosphorus-Centered Functional Groups for Modified Oligonucleotides and Other Natural Phosphates

A. Gautier, C. Lopin, G. Garipova, O. Dubert, I. Kalinina, C. Salcedo, S. Balieu, S. Glatigny, J. Valnot, G. Gouhier and S. Piettre* email
Laboratoire des Fonctions Azotées et Oxygénées Complexes, IRCOF-Université de Rouen, France
* Author to whom correspondence should be addressed.
Received: 23 April 2005 / Accepted: 30 September 2005 / Published: 30 September 2005
(This article belongs to the Special Issue Selected Papers from the “2nd International Conference on Natural Products and Physiologically Active Substances” (ICNPAS-2004) and the 3rd EuroAsian Heterocyclic Meeting “Heterocycles in Organic and Combinatorial Chemistry”)
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Abstract: Efforts to develop synthetic methodologies allowing the preparation of α,α– difluorophosphonothioates, α,α–difluorophosphonodithioates, α,α–difluorophosphono- trithioates, and α,α–difluorophosphinates are reviewed in the light of applications in the field of modified oligonucleotides and cyclitol phosphates. Two successful approaches have been developed, based either on the addition of phosphorus-centered radicals onto gem–difluoroalkenes or on a process involving the addition of lithiodifluorophosphono- thioates 91 onto a ketone and the subsequent deoxygenation reaction of the adduct. The radical route successfully developed a practical route to α,α–difluoro–H–phosphinates which proved to be useful intermediates to a variety of phosphate isosters. The ionic route led to the first preparation of phosphonodifluoromethyl analogues of nucleoside– 3’–phosphates.
Keywords: Phosphate isoster; difluorophosphonates; difluoro-H-phosphinates; nucleotide analogue; cyclitol analogue.

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MDPI and ACS Style

Gautier, A.; Lopin, C.; Garipova, G.; Dubert, O.; Kalinina, I.; Salcedo, C.; Balieu, S.; Glatigny, S.; Valnot, J.; Gouhier, G.; Piettre, S. The Preparation of New Phosphorus-Centered Functional Groups for Modified Oligonucleotides and Other Natural Phosphates. Molecules 2005, 10, 1048-1073.

AMA Style

Gautier A, Lopin C, Garipova G, Dubert O, Kalinina I, Salcedo C, Balieu S, Glatigny S, Valnot J, Gouhier G, Piettre S. The Preparation of New Phosphorus-Centered Functional Groups for Modified Oligonucleotides and Other Natural Phosphates. Molecules. 2005; 10(9):1048-1073.

Chicago/Turabian Style

Gautier, A.; Lopin, C.; Garipova, G.; Dubert, O.; Kalinina, I.; Salcedo, C.; Balieu, S.; Glatigny, S.; Valnot, J.; Gouhier, G.; Piettre, S. 2005. "The Preparation of New Phosphorus-Centered Functional Groups for Modified Oligonucleotides and Other Natural Phosphates." Molecules 10, no. 9: 1048-1073.

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