Collect. Czech. Chem. Commun. 1997, 62, 83-98

Conformational Studies on Diribonucleoside Monophosphate Analogs Containing a Nonisosteric, Isopolar, Phosphonate-Based Internucleotide Linkage

Jaroslav Zajíčeka, Ivan Rosenbergb, Radek Liboskab, Zdeněk Točíkb, G. Victor Fazakerleyc, Wilhelm Guschlbauerc and Antonín Holýb

a Department of Chemistry and Biochemistry, University of Notre Dame, Notre Dame, Indiana 46556, U.S.A.
b Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, 166 10 Prague 6, Czech Republic
c CEA/Saclay, Service de Biochimie et Génétique Moléculaire, F-91199 Gif-sur-Yvette Cedex, France


Two types of (2'-5') and (3'-5') isomers of phosphonate analogs of diribonucleotides derived from 2'-, 3'- or 5'-O-phosphonomethyl ribonucleosides, that differ in the position of methylene group in the phosphonate internucleotide linkage, have been studied in aqueous solution by NMR techniques in order to compare their basic structural features with those of the natural (3'-5') diribonucleotides. Despite the additional methylene group in the ribose-phosphate backbone, dinucleoside phosphonates are structurally and conformationally very similar to their natural counterparts.

Keywords: Conformation; Diribonucleotide analogs; Phosphonates.