Synthesis of 1,5-Anhydro-D-mannitol Nucleosides with a Purine Base Moiety. -A facile synthesis of new arabinohexitol nucleosides as potent antiviral agents and building blocks for the synthesis of oligonucleotides is reported.
Synthesis and antiviral activity of 2-deoxy-1,5-anhydro-D-mannitol nucleosides containing a pyrimidine base moiety
✍ Scribed by María-Jesús Pérez-Pérez; Erik De Clercq; Piet Herdewijn
- Publisher
- Elsevier Science
- Year
- 1996
- Tongue
- English
- Weight
- 210 KB
- Volume
- 6
- Category
- Article
- ISSN
- 0960-894X
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✦ Synopsis
Nucleoside analogues containing a 2-deoxy-l,5-anhydro-D-mannitol and a pyrimidine base moiety were synthesized starting from D-glucose via a nucleophilie opening of an epoxide with the heterocyelic base and an inversion of configuration at the 3'-position. Study of the conformation of these molecules, that show some activity against herpesviruses fflSV, VZV, CMV) should increase our understanding of the structural requirements of hexitol nucleosides for antiviral activity.
📜 SIMILAR VOLUMES
Synthesis of the title compounds can be achwed by nucleophlhc ad&tton of lithmm salts of TMSacetylene and I-hexyne to 2'-ketoundme followed by ra&cal deoxygenatlon of the correspondmg methoxaryl ester