Iminosugars, including mono- and bicyclic type that have found wide attraction both as synthetic targets and as potential therapeutic agents for the treatment of a variety of diseases such as diabetes, viral infection, and lysosomal storage disorders. Currently, this typed polyhydroxylated alkaloid has been applied to manipulate or inhibit biological functions of various sugar-processing enzymes like glycosidase and glycosyltransferases. In our previous reports, we have successfully prepared all possible stereoisomers (16 members) of monocyclic pyrrolidine-typed iminosugars bearing four chiral centers, three hydroxyl groups, and one amino group called an amino-DMDP (ADMDP) based library. Inspired by our previous work, well-established chemical transformation, and the scaffold of naturally occurring alkaloid, swainsonine, we develop a concise route toward the synthesis of bicyclic iminosugars with desired and varied ring sizes and chiral centers. With such unique scaffolds, further molecular libraries containing bicyclic ring system plus substituent and configuration diversity are preparing to build a diverse bicyclic iminosugar-based library. This diverse and versatile small molecule library will be applied to investigate the inhibitory activity against various disease associated sugar-processing enzymes including human α-Mannosidases.

Inspired from naturally occurring bicyclic iminosugars to develop new molecular scaffolds and libraries

254th National Meeting (2017)

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