Selective multiple labeling strategy to obtain accurate NMR parameters for nucleic acids. Conformational analysis around the glycosidic bond.
A systematic synthesis of pyrimidine nucleosides with 13C-labels only at specific atoms in both the base and sugar moieties has been developed in order to obtain conformational information about the glycosidic bond through measurement of the accurate vicinal coupling constants between H1' and C2/C6. For this purpose, 13C labels at three positions, namely C1', C2, and C6, are essential. We have synthesized selectively multiply labeled nucleosides, such as [2, 1'-13C2]-thymidine, [2, 1'-13C2]-2'-deoxycytidine, [6, 1'-13C2]-thymidine, and [6, 1'-13C2]-2'-deoxycytidine. These nucleosides will be useful to determine the relative orientation of the base and sugar moieties.
Ono
A
A
Department of Chemistry, Faculty of Science, Tokyo Metropolitan University, Japan.
Takaishi
N
N
Tatebe
M
M
Ono
A
A
Tate
S
S
Kainosho
M
M
D002247:Carbon Isotopes; D003841:Deoxycytidine; D006027:Glycosides; D007553:Isotope Labeling; D008968:Molecular Conformation; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular / Q000379:methods; D009690:Nucleic Acid Conformation; D011741:Pyrimidine Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry*; D015203:Reproducibility of Results; D013936:Thymidine
D002247:Carbon Isotopes; D006027:Glycosides; D011741:Pyrimidine Nucleosides; D003841:Deoxycytidine; D013936:Thymidine