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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
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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

Chirakul, Panadda; Sigurdsson, Snorri Th

American Chemical Society (ACS)

Biochemistry, Genetics and Molecular Biology; Chemistry

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