Concise synthesis of a heptasaccharide antigen found in the cell-wall lipopolysaccharide of Mycobacterium gordonae strain 990

Abstract

A straight forward synthesis of a heptasaccharide part of the cell-wall lipopolysaccharide of Mycobacterium gordonae strain 990, known to have antigenicity, has been achieved in excellent yield. Judicious choice of protecting groups in the intermediates played a significant role throughout the synthesis. Most of the intermediate steps furnished satisfactory yield.

First Total Synthesis of Trehalose‐Containing Branched Oligosaccharide OSE‐1 of Mycobacterium gordonae (Strain 990)

“…reported the synthesis of the terminal, branched tetrasaccharide of OSE‐1 11. Misra and co‐workers reported a linear synthesis of the heptasaccharide 12. However, these fragments lack the biologically important 6′‐OMe 1,1′‐α,α‐trehalose moiety.…”

“…[11] Misra and co-workers reported alinear synthesis of the heptasaccharide. [12] However,t hese fragments lack the biologically important 6'-OMe 1,1'-a,a-trehalose moiety.I n continuation of our studies towards the synthesiso ft rehalose glycoconjugates, [13] herein we report the first total synthesis of OSE-1.…”

Lipooligosaccharides from Mycobacteria: Structure, Function, and Synthesis

“…Later in 2008, the same group described the preparation of a heptasaccharide fragment of the M. gordonae strain 990 LOS using an analogous route 43…”

Synthesis of the Mycobacterium tuberculosis Canetti Lipooligosaccharide II Nonasaccharide

“…Among these molecules, one of the least studied groups is the lipooligosaccharides (LOSs), which consist of an acylated trehalose core functionalized with a species-specific oligosaccharide, ranging in length from one to as many as 11 monosaccharides, often containing unique structural motifs. In addition to them being potent inducers of antibodies, recent investigations support a role for LOSs in sliding motility, biofilm formation, and the infection of host macrophages. − However, their precise role in mycobacterial virulence remains unclear, and despite their importance, relatively little effort has been directed at synthesizing these compounds as biological tools. − …”