Synthesis of stereoselectively 5'-monodeuterated nucleoside with defined S/R-ratios. An application to the assignment of 5'-methylene signals of DNA oligomers.
A method to prepare 5'-monodeuterated nucleosides with various S/R-ratios is described. 5-Oxopentose derivatives synthesized from glucose were converted into 5-monodeuterated pentose derivatives by LiAID4 in the presence of various ligands. The stereoselectivities of the deuteration reactions were investigated under a variety of conditions, and the S/R-ratios of the 5-monodeuterated pentoses varied from 4 : 1 to 1 : 7.4. By mixing these 5-monodeuterated pentose derivatives, we have successfully synthesized thymidine with a defined S/R-ratio at C5'.
Oogo
Y
Y
Department of Chemistry, Faculty of Science, Tokyo Metropolitan University, Japan.
Ono
A
A
Tate
S
S
Ono
A
A
Kainosho
M
M
D002247:Carbon Isotopes; D004247:DNA / Q000138:chemical synthesis / Q000737:chemistry*; D003903:Deuterium; D005947:Glucose; D007553:Isotope Labeling / Q000379:methods; D008968:Molecular Conformation; D015394:Molecular Structure; D009705:Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry*; D009838:Oligodeoxyribonucleotides / Q000138:chemical synthesis / Q000737:chemistry*; D010429:Pentoses; D013237:Stereoisomerism
D002247:Carbon Isotopes; D009705:Nucleosides; D009838:Oligodeoxyribonucleotides; D010429:Pentoses; D004247:DNA; D003903:Deuterium; D005947:Glucose