title: On the stereochemistry of C3'-O-P-CH2-O-C4'' phosphonate internucleotide bond, a phosphate isostere.
abstract: The work deals with structural evaluation of the internucleotide phosphonate C3'-O-P-CH2-O-C4'' linkage which is an isosteric alternative to natural phosphodiester bond. A thorough description of its stereochemical features was made possible now by matching the results from additional NMR data obtained from the synthesised (13)C-labeled dimeric model compounds and the new findings provided by the extended MDS and ab initio studies. It completed the earlier assumptions. The obtained overall picture in terms of specifying the linkage conformational preferences shows explicitly why the respective phosphonate oligonucleotides differ in properties from those with related phospodiester chain.
authors.affiliation: Institute of Organic Chemistry and Biochemistry, Czech Academy of Sciences, Flemingovo 2, 16610 Prague 6, Czech Republic.
authors.forename: Zdenĕk
authors.initials: Z
authors.lastname: Tocík
authors.forename: Milos
authors.initials: M
authors.lastname: Budĕsínský
authors.forename: Ivan
authors.initials: I
authors.lastname: Barvík
authors.forename: Ivan
authors.initials: I
authors.lastname: Rosenberg
mesh_terms: D003198:Computer Simulation; D009690:Nucleic Acid Conformation; D063065:Organophosphonates / Q000737:chemistry*; D011740:Pyrimidine Dimers / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D063065:Organophosphonates; D011740:Pyrimidine Dimers