Deoxygenated cyclophellitol derivatives: synthesis and applications

Abstract

Cyclophellitol derivatives constitute the majority of existing activity-based probes (ABPs) for the family of retaining glycosidases and have been applied to track glycosidase activity in miscellaneous biological samples and models. Whereas the majority of cyclophellitol derivatives are designed to mimic their natural substrate counterparts, modification of the substitution pattern, in particular deoxygenation, is envisioned to be a useful tool to tune their reactivity and pharmacokinetic properties. This thesis describes the development of synthetic approaches towards 3-deoxy and 3,6-dideoxy cyclophellitol derivatives, their biochemical evaluation and incorporation in the drug design of the potential therapeutics.