This document proposes labeling trehalose glycolipids in the cell wall of Mycobacterium tuberculosis with trehalose analogues containing azide groups. The azide-modified trehalose would bind to the glycolipids, and then bioorthogonal ligation would occur. Experiments are proposed to determine if the analogues label the glycolipids via the Ag85 pathway or recycling pathways by comparing labeling when the SugABCLpqY trehalose transporter is present or absent. The goal is to better understand the metabolism, reactions and biosynthesis of M. tuberculosis' complex cell wall.