Stereospecific syntheses of 3′-deuterated pyrimidine nucleosides and their site-specific incorporation into DNA
Organic Letters, ISSN: 1523-7060, Vol: 5, Issue: 6, Page: 917-919
2003
- 12Citations
- 19Captures
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Metrics Details
- Citations12
- Citation Indexes12
- 12
- CrossRef10
- Captures19
- Readers19
- 19
Article Description
(Matrix presented) 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.
Bibliographic Details
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