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A novel class of glycosidase inhibitors : ammonium, selenonium, and sulfonium sulfates
| Content Provider | Semantic Scholar |
|---|---|
| Author | Ghavami, Ahmad |
| Copyright Year | 2003 |
| Abstract | This thesis focuses on the design and synthesis of a novel class of compounds, namely ammonium, selenonium, and sulfonium sulfates, as glycosidase inhibitors, and also the investigation of their enzyme inhibitory activities. A sulfonium ion, salacinol, is one of the active principles in the aqueous extracts of the plant Salacia reticulata that are traditionally used in Sri Lanka and India for the treatment of type II diabetes. In order to establish the absolute configuration of salacinol and to further investigate the potential of this novel class of inhibitors, a general synthetic route has been designed that afforded salacinol, its different stereoisomers, and the hitherto unknown nitrogen and selenium congeners. The inhibitory activities of the candidate glycosidase inhibitors have been examined with different amylases and glucoamylase G2. Enzyme inhibition assays showed that the type of heteroatom and stereochemistry at the different stereogenic centres of the candidate inhibitors play significant roles in discriminating between different glycosidase enzymes. It follows that alterations of these centres, based on an understanding of the atomic interactions between the compounds and their target enzymes, could be a powerful approach to the design of the next generation, high affinity inhibitors. These inhibitors have potential for inhibition of pancreatic a-amylase and intestinal glucosidases, and hence the treatment of type II diabetes. Inhibition of glycosidase enzymes involved in carbohydrate processing of glycoproteins has also been effective in the treatment of some other disorders such as metastatic cancer. Accordingly, the salacinol-related family of compounds was examined as |
| File Format | PDF HTM / HTML |
| Alternate Webpage(s) | http://summit.sfu.ca/system/files/iritems1/8485/b30940357.pdf |
| Language | English |
| Access Restriction | Open |
| Content Type | Text |
| Resource Type | Article |
