Stereospecific syntheses of 3'-deuterated pyrimidine nucleosides and their site-specific incorporation into DNA |
| |
Authors: | Chirakul Panadda Sigurdsson Snorri Th |
| |
Institution: | Department of Chemistry, University of Washington, Seattle, Washington 98195-1700, USA. |
| |
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. |
| |
Keywords: | |
本文献已被 PubMed 等数据库收录! |
|