Production of oligosaccharides by using cells with a view of constructing the functional nano-structure

Abstract

The efficiency of biocombinatorial synthesis of oligosaccharides using glycoside primers and cells was validated using various primers. Dodecyl b-lactoside primers with different functional groups (vinyl, azido, fluoroalkyl) at the aglycon unit were synthesized and introduced in B16 cells as substrates for sialylation. These primers are synthetically accessible and generally, were prepd. in two steps: glycosylation of a saccharide deriv. with a com. available acceptor in the presence of a Lewis acid, followed by deprotection. Inclusion of functional groups to the appropriate length (C12) of the aglycon unit scarcely affected cell viability and morphol. The presence of the fluorous tag and functional groups, such as vinyl and azido, at the aglycon unit allowed the cellular entry of primers and release after elongation. However, careful consideration of the hydrophilic and hydrophobic balance, generated by the saccharide and aglycon moieties, resp., is necessary to ensure assimilation of glycoside primers into cells. The aglycon unit does not affect sialylation but the saccharide unit does. Although sialyl transferases permit certain modifications in substrate structure, a terminal galactose is important for cellular enzyme-catalyzed sialylation. The sialyl transferases elongated the lactoside primers to yield GM3-type oligosaccharides. [on SciFinder (R)]