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Glycosidase inhibitors are important compounds that can interfere with several biosynthetic processes including N-linked glycosylation and the biosynthesis of several glycoproteins. Understanding the biogenesis of naturally occurring glycosidase inhibitors would be a crucial step towards the chemical synthesis of analogues of choice. This review focuses on the current knowledge regarding the biosynthesis of a series of polyhydroxylated saturated nitrogen heterocycles including nojirimycin and swainsonine among others, with a potent biological activity as inhibitors of glycosidases and transglycosidases.