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Synthesis of stereoselectively 5'-monodeuterated nucleoside with defined S/R-ratios. An application to the assignment of 5'-methylene signals of DNA oligomers

Oogo, Y.; Ono, A.; Tate, S.; Ono, A.; Kainosho, M.

Nucleic Acids Symposium Series 37: 35-36

1997

ISSN/ISBN: 0261-3166
PMID: 9585986
Document Number: 471903
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'.

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