An extensive review of studies on mycobacterium cell wall polysaccharide-related oligosaccharides – part I: Synthetic studies on arabinofuranosyl oligosaccharides

Abstract

Lipoarabinomannan (LAM), mannosyl LAM (ManLAM), and mycolyl-arabinogalactan (mAG) are unique and ubiquitous cell wall constituents of Mycobacterium tuberculosis (M. tb), the bacterium causing tuberculosis (TB), one of the deadliest diseases worldwide. It has been well documented that LAM, ManLAM, and mAG play an important role in mycobacterial infections and in the elicitation of specific immune responses against M. tb in the host. Therefore, LAM, ManLAM, mAG, and related molecules are attractive targets for the development of novel diagnostic and therapeutic strategies for TB. Accordingly, great research efforts have been spent on the chemical synthesis and biological studies of mycobacterium-related arabinofuranosyl oligosaccharides and their mimetics and conjugates. This article provides an extensive review about the progresses in this area. Due to the page limit of the journal, this review is published separately in three parts. Part I is focused on various glycosylation methods or strategies and protection tactics for stereoselective and stereospecific construction of α- and β-arabinofuranosyl linkages, as well as their applications to the synthesis of simple to highly complex mycobacterium-related arabinofuranosyl oligosaccharides containing only α-linked or both α- and β-linked arabinofuranosyl residues.