Stereoselective synthesis 2-C-alkylglucosides, potential inhibitors of mycobacterial MshB and related enzymes

• Main Author: Muhunga, Denis Ngumbu
• Other Authors: Gammon, David W
• Format: Dissertation
• Language: English
• Published: University of Cape Town 2015
• Subjects: Chemistry
• Online Access: http://hdl.handle.net/11427/12396

Includes bibliographical references (leaves 69-72). === Tuberculosis (TB) is one of the world's most deadly diseases and kills approximately 1.7 million people each year. The developing resistance of TB to the two most common anti-TB drugs (isoniazid and rifampicin) proves the urgency of the current situation. The MshB reducing agent exclusively in the actinomycetes is used as a model for the development of new anti-TB drugs. It was shown that the stereoselectivity synthesis of C-2 alkyl glucoside gave a key intermediate for the suitable synthesis of glycosyl donors. In addition, we achieved the preparation of D-inositol derivative chirally pure and having the hydroxyl at the 1-position. However, the attempted glycosylation reaction failed to give the desired product.