Rapid, iterative assembly of octyl α-1,6-oligomannosides and their 6-deoxy equivalents

Abstract

Mycobacterium tuberculosis is the cause of the deadly human disease tuberculosis. In studies over the last 40 years it has been revealed that this organism possesses a complex cell wall including glycophospholipids such as the phosphatidylinositiol mannosides (PIMs), lipomannan (LM) and lipoarabinomannan (LAM). These glycolipids all contain a common α-1,6-linked mannoside core, and the higher PIMs and LAM possess α-1,2-linked mannosyl residues. It has been shown that simple α-1,6-linked oligomannosides can act as substrates for α-1,6-mannosyltransferases in mycobacteria. Here we report a simple iterative synthesis of a series of hydrophobic octyl α-1,6-linked oligomannosides from mono- throu..