Selective oxidation of glycosides
| PhD ceremony: | Mr M. Jäger |
| When: | June 26, 2015 |
| Start: | 09:00 |
| Supervisor: | prof. dr. ir. A.J. (Adriaan J) Minnaard |
| Where: | Academy building RUG / Student Information & Administration |
| Faculty: | Science and Engineering |
Carbohydrates are the most abundant class of natural products and can be found in all forms of life. The chemical synthesis of carbohydrates due to the similar reactivity of the hydroxyl groups, relies often on long and inefficient protection and deprotection strategies. For that reason we developed a method for the selective oxidation of carbohydrates, which enables selective modification and rapid access to derivatives of commercial carbohydrates.
As a first application we turned our attention to antibiotics. Multi-resistant bacteria form a major threat to mankind, therefore the development of novel antibiotics is highly desired. Aminoglycosides antibiotics are an important class of antibiotics, which are especially important in intensive care medication to treat a range of severe bacterial infections like e.g. endocarditis, sepsis or (resistant) mycobacterial infections and are used alone as well as in combination with other antibiotics.
We successfully applied the concept of the selective oxidation to aminoglycosides. The impressive selectivity of the oxidation was shown by the transformation of several antibiotics to the corresponding keto-aminoglycosides, which allow further functionalization in a minimum of synthetic steps. Therefore giving chemist a new tool for the development of novel antibiotics against resistant strains of bacteria.