具有特定S/R比例的立体选择性5'-单氘代核苷的合成。在DNA寡聚物5'-亚甲基信号归属中的应用。

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

作者信息

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

机构信息

Department of Chemistry, Faculty of Science, Tokyo Metropolitan University, Japan.

出版信息

Nucleic Acids Symp Ser. 1997(37):35-6.

PMID:9585986

Abstract

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'.

摘要

描述了一种制备具有不同S/R比的5'-单氘代核苷的方法。由葡萄糖合成的5-氧代戊糖衍生物在各种配体存在下通过LiAID4转化为5-单氘代戊糖衍生物。在各种条件下研究了氘代反应的立体选择性，5-单氘代戊糖的S/R比在4:1至1:7.4之间变化。通过混合这些5-单氘代戊糖衍生物，我们成功地合成了在C5'处具有确定S/R比的胸苷。