Highly regioselective galactosylation of floxuridine catalyzed by beta-galactosidase from bovine liver.
5'-O-beta-D-Galactosyl-floxuridine, a potential novel prodrug, was synthesized with a yield of 75% through beta-galactosidase-catalyzed transgalactosylation. This enzyme displayed absolute regioselectivity toward the 5'-position of floxuridine. For the reaction, the optimal conditions were pH 6.5 at 45 degrees C for 60 h with floxuridine to o-nitrophenyl-beta-D-galactoside at 2:1 (mol/mol). Under these conditions, the initial reaction rate and the maximum yield were 0.28 mM h(-1) and 75%, respectively.
Zeng
Quan-Ming
QM
State Key Laboratory of Pulp and Paper Engineering, College of Light Industry and Food Sciences, South China University of Technology, Guangzhou 510640, China.
Li
Ning
N
Zong
Min-Hua
MH
D000818:Animals; D002417:Cattle; D004795:Enzyme Stability; D005467:Floxuridine / Q000737:chemistry / Q000378:metabolism*; D006863:Hydrogen-Ion Concentration; D007700:Kinetics; D008099:Liver / Q000201:enzymology*; D009598:Nitrophenylgalactosides / Q000378:metabolism; D011355:Prodrugs / Q000737:chemistry / Q000378:metabolism; D013379:Substrate Specificity; D013696:Temperature; D013997:Time Factors; D001616:beta-Galactosidase / Q000302:isolation & purification* / Q000378:metabolism*
D011355:Prodrugs; D005467:Floxuridine; C055012:2-nitrophenylgalactoside; D009598:Nitrophenylgalactosides; D001616:beta-Galactosidase