Regioselective enzymatic acylation of ribavirin to give potential multifunctional derivatives.
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%.
Liu
Bo-Kai
BK
Department of Chemistry, Zhejiang University, 310027, Hangzhou, P.R. China.
Wang
Na
N
Wu
Qi
Q
Xie
Chuan-Ying
CY
Lin
Xian-Fu
XF
D000096:Acetone / Q000737:chemistry; D000215:Acylation; D000475:Alkenes / Q000737:chemistry / Q000378:metabolism; D002070:Butadienes / Q000737:chemistry / Q000378:metabolism; D002175:Candida / Q000201:enzymology*; D002855:Chromatography, Thin Layer; D003998:Dicarboxylic Acids / Q000737:chemistry / Q000378:metabolism; D004800:Enzymes, Immobilized / Q000737:chemistry / Q000378:metabolism; D008049:Lipase / Q000737:chemistry / Q000378:metabolism*; D012254:Ribavirin / Q000737:chemistry / Q000378:metabolism*; D013379:Substrate Specificity
D000475:Alkenes; D002070:Butadienes; D003998:Dicarboxylic Acids; D004800:Enzymes, Immobilized; D000096:Acetone; D012254:Ribavirin; D008049:Lipase; C031763:1,3-butadiene