Transglycosylation behavior of Mucor hiemalis endo-β-N-acetylglucosaminidase to β-cyclodextrin derivatives with multivalent glucose moieties for synthesizing cyclodextrin-based oligosaccharide clusters

Abstract

We investigated the transglycosylation reaction of two types of oligosaccharide acceptors, i.e., β-cyclodextrin (CD) derivatives 1 and 2 conjugated with multiple glucose (Glc) units, catalyzed by endo-β-N-acetyl-glucosaminidase from Mucor hiemalis (Endo-M) using the oligosaccharide donor sialoglycopeptide (SGP). The acceptor specificity of the enzyme transglycosylation of 1 and 2 having seven Glc moieties within small nanoscale spatial regions on the β-CDs was investigated on the basis of the effect of the molar ratios of SGP to acceptors 1 or 2 with different spatial configurations on the transglycosylation behavior. The formation of the corresponding CD-based oligosaccharide clusters from Endo-M was also evaluated.

Keywords: Endo-M; Oligosaccharide-cluster; Sialoglycopeptide; Transglycosylation; endo-β-N-Acetyl-glucosaminidase; β-cyclodextrin.