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  • Title: Stereospecific syntheses of 3'-deuterated pyrimidine nucleosides and their site-specific incorporation into DNA.
    Author: Chirakul P, Sigurdsson ST.
    Journal: Org Lett; 2003 Mar 20; 5(6):917-9. PubMed ID: 12633105.
    Abstract:
    [reaction: see text] 2'-Deoxy-3'-deutero pyrimidines have been synthesized in high yields and incorporated into deoxyoligonucleotides using standard phosphoramidite chemistry. A key synthetic step is a stereospecific reduction of 3'-keto nucleosides using sodium triacetoxyborodeuteride to give 3'-deuterated thymidine and 2'-deoxy uridine nucleosides. Conversion of the corresponding phorphoramidites 7a and 7b to 4-triazolo derivatives has, for the first time, enabled incorporation of 2'-deoxy-3'-deutero cytidine and 2'-deoxy-3'-deutero-5-methyl cytidine into oligonucleotides.
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