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Highly efficient diastereoselective biocatalytic acylation of a diastereotopic furanose diol and synthesis of key intermediates for amino derivatized bicyclonucleosides |
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| Authors: | Ashok K PrasadSucharita Roy Rajesh Kumar Neerja KalraJesper Wengel Carl E OlsenAshok L Cholli Lynne A SamuelsonJayant Kumar Arthur C WattersonRichard A Gross Virinder S Parmar |
| Institution: | a Bioorganic Laboratory, Department of Chemistry, University of Delhi, Delhi 110 007, India b Department of Chemistry, Institute for Nano Science and Engineering Technology, University of Massachusetts, One University Avenue, Lowell, MA 01854, USA c NSF Center for Biocatalysis and Bioprocessing of Macromolecules, Department of Chemistry, Polytechnic University, Six Metrotech Center, Brooklyn, NY 11201, USA d Department of Chemistry, University of Southern Denmark, DK-5230 Odense M, Denmark e Department of Chemistry, Royal Veterinary and Agricultural University, DK-1871 Copenhagen, Denmark |
| Abstract: | The selectivity of Candida antarctica lipase has been demonstrated and employed in the manipulation of a diastereotopic furanose diol as the key step in the synthesis of a novel bicyclo 3-amino-3-deoxy furanose derivative, which is an important intermediate for the synthesis of bicyclic analogs of AZT. The asymmetrization of the diol has been achieved with preferred formation of a monoacylated product with 100% diastereoselectivity. An efficient synthesis of an intermediate in the synthesis of amino derivatized bicyclonucleosides is also described, two such novel compounds containing cycloamino residues have been prepared. |
| Keywords: | biocatalysis lipase acylation diastereoselectivity bicyclonucleoside |
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