Total Synthesis of Campylobacter jejuni NCTC11168 Capsular Polysaccharide via the Intramolecular Anomeric Protection Strategy

Abstract

The infection of Campylobacter jejuni results in a significant diarrhea disease, which is highly fatal to young children in unindustrialized countries. Developing a new therapy is required due to increasing antibiotic resistance. Herein, we described a total synthesis of a C. jejuni NCTC11168 capsular polysaccharide repeating unit containing a linker moiety via an intramolecular anomeric protection (iMAP) strategy. This one-step 1,6-protecting method structured the challenging furanosyl galactosamine configuration, facilitated further concise regioselective protection, and smoothed the heptose synthesis. The tetrasaccharide was constructed in a [2 + 1 + 1] manner. The synthesis of this complicated CPS tetrasaccharide was completed in merely 28 steps, including the preparation of all the building blocks, construction of the tetrasaccharide skeleton, and functional group transformations.