An enzymatic glycosylation of nucleoside analogues using β-galactosidase from Escherichia coli

Abstract

A new enzymatic method for the synthesis of beta-galactosides of nucleosides and acyclic nucleoside analogues has been developed, using beta-galactosidase from Escherichia coli as a catalyst and lactose as a sugar donor. The method is very rapid, feasible and last but not least inexpensive.

Its applicability has been proven for a broad variety of possible substrates with respect to its scaling up for preparative use. Five new compounds from a series of nucleoside and acyclic nucleoside analogues have been prepared on a scale of several hundred milligrams, in all cases revealing very good results of the method concerning the reproducibility of the reaction yields and simplicity of the purification process.

Keywords

• glycosylation
• galactosylation
• beta-galactosidase
• prodrug
• enzymatic synthesis
• nucleoside
• acyclic nucleoside analogues