Concise synthesis of the tetrasaccharide repeating unit of the O-antigen from Escherichia coli O131 containing N-acetyl neuraminic acid

Abstract

Synthesis of the tetrasaccharide repeating unit of the O-antigen from E. coli O131 was accomplished through a linear strategy involving rationally protected monosaccharide units derived from commercially available sugars. The challenging α-glycosylation of N-acetyl neuraminic acid was achieved through activation of thioglycoside using NIS-mediated glycosylation strategy. The target tetrasaccharide in the form of its 3-aminopropyl glycoside may be used for further glycoconjugate formation without hampering the anomeric stereochemistry.

Keywords: E. coli; N-acetyl neuraminic acid; O-antigen; Stereoselective glycosylation; Total synthesis.