ABSTRACT
Fast and simple methodology for the assignment of the absolute configuration at the phosphorus atom in diastereomerically pure RP and SP 5′-O-monomethoxytrityl-2′-O-deoxynucleoside 3′-O-(O-4-nitrophenyl)methanephosphonate (3) was established. The method utilizes 2D ROESY NMR and can be used for the stereochemical analysis of other P-chiral mononucleotides. Configurational analysis shows that the major conformation of the sugar residue in 3 is of the S (South) type. This study will facilitate synthesis of stereoregular methylphosphonate oligonucleotide analogues via the transesterification method.
ACKNOWLEDGMENTS
Supported in part by the Polish Foundation for the Promotion of Science (FNP), Project Phare SCI-TECH II, grant number PL9611/98/03-02.9, Polish Committee for Scientific Research (KBN) grant number 6 PO5F 023 20p02 and Technical University of Lodz.