First Synthesis of Pentasaccharide Glycoform I of the Outer Core Region of the Pseudomonas aeruginosa Lipopolysaccharide

Abstract

The synthesis of a pentasaccharide representing the glycoform I, which is one of two naturally occurring glycoforms of the outer core of Pseudomonas aeruginosa lipopolysaccharide, and its analogues, differing in the N-substituent in the galactosamine unit, is reported. The main features of the synthetic scheme included the assembly of the pentasaccharide backbone by successive introduction of monosaccharide units, the use of glucosyl donors with specific location of acyl protecting groups capable of the remote anchimeric participation for highly stereoselective alpha-glucosylation, and efficient reduction of the azido group allowing high-yielding transformation of the intermediary azido pentasaccharide into final products.