Date of Award:


Document Type:


Degree Name:

Master of Science (MS)


Chemistry and Biochemistry


Tom Chang


In this study, we investigated the potential applications of carbohydrates in the development of new antibiotics. To tackle the problem of multidrug-resistant variants of M. tuberculosis (MDR-TB), we investigated the biosynthesis pathways of trehalose, which has contributed to significant drug resistance. Some new methods were

developed for the synthesis of potential inhibitors (6-azido-trehalose and 6,6'-diazido-trehalose) that have been designed to imitate the intermediate molecule (trehalose 6-phosphate, TPP) of OtsA-OtsB pathway. At the same time, some new antibacterial agents based on trehalose have been synthesized. Members of the 1,2,3-triazole family have shown interesting biological properties.

Steroid derivatives have been developed in antibiotics area. Therefore click reaction was utilized to build a 1,2,3-triazole ring and combine cholesterol with different carbohydrate moieties. A series of new compounds has been synthesized and their bioactivities have been tested.