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Abstract Acinetobacter baumannii is a Gram‐negative bacteria associated with drug resistance and infection in healthcare settings. An understanding of both the biological roles and antigenicity of surface molecules of this organism may provide an important step in the prevention and treatment of infection through vaccination or the development of monoclonal antibodies. With this in mind, we have performed the multistep synthesis of a conjugation‐ready pentasaccharide O ‐glycan from A. baumannii with a longest linear synthetic sequence of 19 steps. This target is particularly relevant due to its role in both fitness and virulence across an apparently broad range of clinically relevant strains. Synthetic challenges include formulating an effective protecting group strategy as well as the installation of a particularly difficult glycosidic linkage between the anomeric position of a 2,3‐diacetamido‐2,3‐dideoxy‐D‐glucuronic acid and the 4‐position of D‐galactose.more » « less
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We report on our initial results from a systematic effort to implement electron-withdrawing protecting groups and Lewis basic solvents/additives as an approach to 1,2- cis (α)-selective O -glucosylation. 1,2- cis -Selective O -glucosylations are reported with thioglucosides and glucosyl trichloroacetimidates and a range of acceptors. A correlation between electron-withdrawing effects and 1,2- cis selectivity has been established. This phenomenon may prove to be broadly applicable in the area of chemical O -glycosylation.more » « less
