ORGN 527 |
Strategies for synthesis of nucleoside cyclic boranophosphates and boranophosphorothioates
| Ping Li, Kaizhang He, and Barbara R. Shaw. Paul M. Gross Chemical Laboratory, Department of Chemistry, Duke University, Durham, NC 27708-0346 |
Nucleoside 3’,5’-cyclic monophosphates are key regulators of various biochemical processes. Likewise, nucleoside 2’,3’-cyclic monophosphates are important intermediates in the ribonuclease-catalyzed hydrolysis of RNA. Introduction of modifications at the phosphorus center of natural products may be valuable in elucidating mechanisms of enzyme reactions. Such knowledge is of prime importance for the development of new enzyme inhibitors with potential medical use and for the design of new analogues. Here we report general syntheses of analogues of natural nucleoside cyclic monophosphates with mono- and double-modifications, specifically, nucleoside 3’,5’-cyclic boranophosphate (1a) and boranophosphorothioate (1b) and the corresponding nucleoside 2’,3’-cyclic compounds (2a, 2b). |
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Bioorganic, Molecular Recognition, Asymmetric Reactions and Syntheses
11:00 AM-1:00 PM, Wednesday, September 10, 2003 Javits Convention Center -- Hall 1B/1C, Poster
Division of Organic Chemistry
The 226th ACS National Meeting, New York, NY, September 7-11, 2003
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