P-chiral oligonucleotides. 2D Roesy NMR assignment of absolute configuration at phosphorus and conformational analysis of 5'-O-monomethoxytrityl-(2'-O-deoxyribonucleoside) 3'-O-[O-(4-nitrophenyl)]methanephosphonates.
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.
Jankowski
Stefan
S
Technical University of Lodz, Department of Chemistry, Poland.
Olejniczak
Agnieszka B
AB
Lesnikowski
Zbigniew J
ZJ
D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D009841:Oligonucleotides / Q000737:chemistry*; D063065:Organophosphonates / Q000737:chemistry*; D010758:Phosphorus / Q000737:chemistry
D009841:Oligonucleotides; D063065:Organophosphonates; D010758:Phosphorus