Interplay of Monosaccharide Configurations on the Deacetylation with Lipase-B.

Configurational differences in monosaccharides determine the products and selectivity of the transesterification reaction with lipase-B (CAL-B). The β-anomers of peresterified pyranose monosaccharides tend to yield anomeric deprotection products, while the α-anomers preferentially react at the sixth or fourth position. CAL-B differentiates between enantiomers, either reacting more rapidly with d-enantiomers of monosaccharides or having a different selectivity based on the enantiomer.

Synthesis of 6'-galactosyllactose, a deviant human milk oligosaccharide, with the aid of lipase-B.

Research on human milk oligosaccharides (HMOs) has increased over the past decade showing great interest in their beneficial effects. Here we describe a method for the selective deacetylation using immobilised lipase-B, Novozyme N435 (N435), of pyranose saccharides in organic media with the aim of simplifying and improving the pathways for the synthesis of HMOs. By first studying in depth the deacetylation reaction of peracetylated D-glucose two reaction conditions were found, which were used on different HMO building blocks, peracetylated saccharides and thioglycosides.