Characterization of 3-amino-3,6-dideoxy-D-glucose from a bacterial lipopolysaccharide.

Lipopolysaccharides were isolated from Cifrobacfer freundii ATCC 8090 by 44% aqueous-phenol fractionation. The lipopolysaccharides were isolated from the phenol phase and phenol-water interphase fractions. Acid hydrolysis yielded glucosamine and a 3-amino sugar identified as 3amino-3,6-dideoxyglucose by comparison with authentic 3-amino-3,6-dideoxyhexoses by ion exchange chromatography. Comparison of the 3-acetamido-l ,Z ,4-tri-o-acetyl3 ,&dideoxyhexose with 3-acetamido-l , 2,4-tri-0-acetyl-3,6dideoxy-L-glucose was made. The infrared spectra were identical, while the optical rotatory dispersion curves were identical in shape but opposite in sign. The compound isolated from C. freundii was thus assigned the structure 3-amino-3,6-dideoxy-~-glucose.