Stereospecific syntheses of 3'-deuterated pyrimidine nucleosides and their site-specific incorporation into DNA.
[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.
Chirakul
Panadda
P
Department of Chemistry, University of Washington, Seattle, Washington 98195-1700, USA.
Sigurdsson
Snorri Th
ST
D004247:DNA / Q000096:biosynthesis*; D003903:Deuterium; D009682:Magnetic Resonance Spectroscopy; D009841:Oligonucleotides / Q000138:chemical synthesis; D010084:Oxidation-Reduction; D011741:Pyrimidine Nucleosides / Q000138:chemical synthesis*; D021241:Spectrometry, Mass, Electrospray Ionization; D013237:Stereoisomerism
D009841:Oligonucleotides; D011741:Pyrimidine Nucleosides; D004247:DNA; D003903:Deuterium