Synthesis of substrates for the galactofuranosyl transferase GlfT2

Abstract

The galactan, a polymer of galactofuranose (Galf), is a key component of the hydrophobic cell wall of Mycobacterium tuberculosis, the bacterial species that is responsible for tuberculosis. Much remains unknown about the biosynthesis of the galactan, and there is a need for synthetic substrates that will allow study of the essential enzymes involved in galactan biosynthesis. In particular, the galactofuranosyl transferase GlfT2 exhibits interesting enzymatic activities including the ability to generate regioisomeric linkages and polymers of approximately 30 Galf residues. Recent developments in strategies for the chemical synthesis of oligosaccharides have been used to synthesize Galf-containing acceptor substrates. These substrates mimic key features of the structure of the putative endogenous acceptor for GlfT2. The availability of such substrates has been invaluable for the study of this important enzyme, and this work may assist in creating future drugs to treat bacterial diseases such as tuberculosis.