On the stereochemistry of C3'-O-P-CH2-O-C4'' phosphonate internucleotide bond, a phosphate isostere.
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.
Tocík
Zdenĕk
Z
Institute of Organic Chemistry and Biochemistry, Czech Academy of Sciences, Flemingovo 2, 16610 Prague 6, Czech Republic.
Budĕsínský
Milos
M
Barvík
Ivan
I
Rosenberg
Ivan
I
D003198:Computer Simulation; D009690:Nucleic Acid Conformation; D063065:Organophosphonates / Q000737:chemistry*; D011740:Pyrimidine Dimers / Q000737:chemistry*; D013237:Stereoisomerism
D063065:Organophosphonates; D011740:Pyrimidine Dimers