Regioselective enzymatic acylation of ribavirin to give potential multifunctional derivatives
Tóm tắt
Lipase-catalyzed synthesis of potential multifunctional ribavirin derivatives was performed in acetone. Divinyl dicarboxylates with different chain lengths (C4, C6, C9, C10) were used as acyl donors and the reactions were catalyzed by lipase immobilized on acrylic resin from Candida antarctica (CAL-B). Ribavirin was regioselectivly acylated at the primary hydroxyl groups and the corresponding vinyl esters (C4, C6, C9, C10) were prepared in respective yields of 48%, 65%, 54%, 55%.
Tài liệu tham khảo
DA Bisceglie M Shindo TL Fong (1992) ArticleTitleA pilot study of ribavirin therapy for chronic hepatitis C Hepatology 16 649–654 Occurrence Handle1505907
G Distefano FP Colonna A Bongini C Busi A Mattioli L Fiume (1997) ArticleTitleRibavirin conjugated with lactosaminated poly-L-lysine Biochem. Pharmacol 54 357–363 Occurrence Handle10.1016/S0006-2952(97)00223-2 Occurrence Handle9278094
M Ferrero V Gotor (2000) ArticleTitleBiocatalytic selective modification of conventional nucleosides, carbocyclic nucleosides and C-nucleosides Chem. Rev 100 4319–4347 Occurrence Handle10.1021/cr000446y Occurrence Handle11749350
RL Hanson Z Shi DB Brzozowski A Banerjee TP Kissick J Singh (2000) ArticleTitleRegioselective enzymatic aminoacylation of lobucavir to give an intermediate for lobucavir prodrug Bioorgan. Med. Chem 8 2681–2687 Occurrence Handle10.1016/S0968-0896(00)00209-1
AB Jain B Eghtesad R Venkataramanan PA Fontes R Kashyap I Dvorchik AO Shakil L Kingery JJ Fung (2002) ArticleTitleRibavirin dose modification based on renal function is necessary to reduce hemolysis in liver transplant patients with hepatitis C virus infection Liver Transplant 8 1007–1013 Occurrence Handle10.1053/jlts.2002.36241
John EDM, Henry WS, Robert JP (1960) Technology of the synthesis divinyl esters of dicarboxylic acids. British Patent. 827718
S Riva J Chopineau APG Kieboom A Klibanov (1988) ArticleTitleProtease-catalyzed regioselective esterification of sugars and related compounds in anhydrous dimethylformamide J. Am. Chem. Soc 110 584–589 Occurrence Handle10.1021/ja00210a045
K Yoshimoto Y Itatani Y Tsuda (1980) ArticleTitle13C-Nuclear magnetic resonance spectra of O-acylglucose Additivity of shift parameters and its application to structure elucidations Chem. Pharm. Bull 28 2065–2074