A Versatile Synthesis of Pentacosafuranoside Subunit Reminiscent of Mycobacterial Arabinogalactan Employing One Strategic Glycosidation Protocol

Abstract

Oligosaccharides are involved in a myriad of biological phenomena. Many glycobiological experiments can be undertaken if homogenous and well‐defined oligosaccharides are accessible. Mycobacterial cell walls contain arabinogalactan as one of the major constituents that is challenging for chemical synthesis. Therefore, the major aim of this investigation is to synthesise a major oligosaccharide portion of the arabinogalactan. The pentacosafuranoside (25mer) synthesis involved installation of several arabinofuranosidic linkages through neighbouring group participation for 1,2‐trans linkages and oxidation‐reduction strategy for the 1,2‐cis Araf. A strategically placed n‐pentenyl moiety at the reducing end enables ligation of biomolecular probes through celebrated cross metathesis or thiol‐ene click reactions. Several linear and branched oligosaccharides were synthesised ranging from trisaccharide to pentadecasaccharide during this endeavour. Synthesis of pentacosasaccharide was accomplished in 77 steps with 0.0012 % overall yield. These oligosaccharides are envisioned to be excellent probes for understanding disease biology thereby facilitating discovery of novel antitubercular agents, vaccines and/or diagnostics.