Synthesis of a series of novel heteroglycoclusters and homoglycoclusters and the study of their anti-adhesion activities

•A new series of homoglycoclusters and heteroglycoclusters were synthesized.•The anti-adhesion activities of these compounds were assessed by SPR and a static state cell-based assay.•These results did not show significant difference of anti-adhesion activities between flexible scaffold and rigid scaffold.

A new series of mixed-type heteroglycoclusters containing mannose and lactose were synthesized. In the synthesis of rigid scaffold of heteroglycocluster, we found that trans-isomer could be prepared stereoselectively by means of Grubbs olefin cross-metathesis reactions. Moreover, sequential acylation using cyclic anhydride as scaffold could give cis-isomer. These two methods may provide complementarity of stereochemistry in heteroglycocluster assembling. The anti-adhesion activities of these compounds were assessed by Surface Plasmon Resonance (SPR) and static state cell-based adhesion assay. These results indicated that the rigid scaffold might not affect the anti-adhesion activities.

Graphical abstractFigure optionsDownload full-size imageDownload as PowerPoint slide