Lipase-catalyzed protection of the hydroxy groups of the nucleosides inosine and 2'-deoxyinosine: a new chemoenzymatic synthesis of the antiviral drug 2',3'-dideoxyinosine.
The selective acylation of the hydroxy groups of the nucleosides inosine 1a and 2'-deoxyinosine 1b has been achieved in the presence of Candida antarctica and Pseudomonas sp. lipases in organic solvents; starting from the 5'-acetyl derivative of 2'-deoxyinosine, compound 5a, an efficient chemoenzymatic synthesis of the antiviral drug 2',3'-dideoxyinosine 1c has been achieved.
Ciuffreda
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Dipartimento di Scienze Precliniche LITA Vialba-Via G.B. Grassi, Università degli Studi di Milano, Italy.
Casati
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Santaniello
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D000215:Acylation; D019380:Anti-HIV Agents / Q000138:chemical synthesis*; D002175:Candida / Q000201:enzymology; D016049:Didanosine / Q000138:chemical synthesis*; D007288:Inosine / Q000031:analogs & derivatives* / Q000737:chemistry*; D008049:Lipase / Q000378:metabolism*; D008956:Models, Chemical; D011549:Pseudomonas / Q000201:enzymology
D019380:Anti-HIV Agents; D007288:Inosine; D008049:Lipase; C012271:deoxyinosine; D016049:Didanosine