Abstract
A number of natural and synthetic analogues of homoazasugars, known in the literature, are promising glycosidase inhibitors. The methodologies used for the synthesis of piperidine homoazasugars are: (i) intramolecular reductive amination, (ii) intermolecular double reductive amination, (iii) amino/amido mercuration, (iv) intramolecular nucleophilic substitution, (v) synthesis from non-carbohydrate building block and aza-heterocycles and (vi) enzyme catalyzed intramolecular reductive amination. Homoazasugars showed higher selectivity and potency in the glycosidase inhibitory activity. In this report, natural occurrence, synthetic methodologies and potential application to glycosidase inhibitory activity of homoazasugars will be reviewed.
Highlights
The search for selective and effective inhibitors of oligosaccharide processing enzymes has promoted intense research over the last 20 years in the synthesis of stereochemically welldefined polyhydroxylated piperidines
The search for promising glycosidase inhibitors led to the discovery of homoazasugars
A brief review of natural occurrence, synthetic aspects and biological activity of piperidine homoazasugars is described in this article
Summary
The search for selective and effective inhibitors of oligosaccharide processing enzymes has promoted intense research over the last 20 years in the synthesis of stereochemically welldefined polyhydroxylated piperidines. This class of compounds, commonly called as azasugars or iminosugars, are known to be endowed with a remarkable therapeutic potential in the treatment of diabetes, viral infections (including HIV) and tumor metastasis1b due to their action as glycosidase inhibitors.[1] The polyhydroxylated piperidine namely nojirimycin (NJ 1, Figure 1) was first isolated from a fermentation broth of Streptomyces roseochromogenes R-468.2a The more stable form of NJ is the 1-deoxynojirimycin (DNJ, 2), called as moranoline, was first prepared2b by catalytic hydrogenation of NJ and later on isolated from different species of the plant Morus.2c. In other the type carbon homologation is present at C-6 of the piperidine (type II)
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