Preparation of 2'-deoxyribonucleosides with an identically 2H/13C-labeled sugar residue.
Thymidine with the stereoselectively 2H/13C-Labeled sugar moiety, (2'R)(5'S)-[1',2',3',4',5'-(13)C5;2',5'-(2)H2]-thymidine, was synthesized from uniformly 13C-labeled glucose, via the selectively deuterated ribose derivative prepared by the stereo-controlled deuteride transfer reactions. The labeled sugar moiety of the thymidine was then transferred to 2'-deoxyadenosine, 2'-deoxyguanosine, and 2'-deoxyuridine, by the enzymatic transglycosylation reactions by purine and pyrimidine nucleoside phosphorylases, in good yields. Labeled 2'-deoxyuridine was chemically converted to 2'-deoxycytidine. Consequently, all of the 2'-deoxynucleosides prepared by this method has the identically labeled sugar moiety. By using DNA oligomers containing the identically labeled sugar residue for NMR studies, any possible complexity in NMR data analyses expected to be observed for DNA oligomers containing variously labeled nucleosides can be minimized.
Oogo
Y
Y
Department of Chemistry, Faculty of Science, Tokyo Metropolitan University.
Nonaka
K
K
Ono
A M
AM
Ono
A
A
Kainosho
M
M
D002247:Carbon Isotopes; D003839:Deoxyadenosines / Q000138:chemical synthesis; D003841:Deoxycytidine / Q000138:chemical synthesis; D003849:Deoxyguanosine / Q000138:chemical synthesis; D003853:Deoxyribonucleosides / Q000138:chemical synthesis* / Q000737:chemistry; D003857:Deoxyuridine / Q000138:chemical synthesis; D003903:Deuterium; D005947:Glucose; D007553:Isotope Labeling / Q000379:methods; D019906:Nuclear Magnetic Resonance, Biomolecular; D009838:Oligodeoxyribonucleotides / Q000138:chemical synthesis / Q000737:chemistry; D012266:Ribose
D002247:Carbon Isotopes; D003839:Deoxyadenosines; D003853:Deoxyribonucleosides; D009838:Oligodeoxyribonucleotides; D003841:Deoxycytidine; D012266:Ribose; D003903:Deuterium; D003849:Deoxyguanosine; D005947:Glucose; D003857:Deoxyuridine