Stereoselective nucleoside deuteration for NMR studies of DNA.
A procedure has been elaborated for stereoselective deuterium substitution of one of the diastereotopic 5'-protons in 2'-deoxynucleotides. The synthetic scheme uses the reduction of the 5-oxosugar derivative with deuterated Alpine-Borane. The resulting deuterosugar is converted into pyrimidine nucleosides and incorporated into DNA using standard protocols. Comparison of two-dimensional NMR spectra of the fully protonated and partially deuterated duplexes allowed us to assign diastereotopic 5' protons, increasing the number of experimental restraints used for structure determination.
Lukin
Mark
M
Department of Pharmacological Sciences, Stony Brook University, Stony Brook, New York, USA.
de los Santos
Carlos
C
D004247:DNA / Q000737:chemistry*; D004249:DNA Damage; D003903:Deuterium / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D009705:Nucleosides / Q000737:chemistry*; D010084:Oxidation-Reduction; D011522:Protons; D011741:Pyrimidine Nucleosides / Q000737:chemistry; D013237:Stereoisomerism
D009705:Nucleosides; D011522:Protons; D011741:Pyrimidine Nucleosides; D004247:DNA; D003903:Deuterium