Substrate specificity of lipase from Burkholderia cepacia in the synthesis of 3′-arylaliphatic acid esters of floxuridine

Among the five vinyl esters bearing phenyl ring in acyl moiety, the lipase from Burkholderia cepacia was most specific toward vinyl 4-phenylbutyrate. Additionally, 3′-regioselectivity of the enzyme was enhanced with the increment of acyl chain length. The lipophilic 3′-arylaliphatic acid esters of floxuridine, its potential prodrugs, were synthesized with high conversions (>98%) and good to excellent regioselectivities (85–99%) via the enzymatic approach.