Preparative production and separation of 2-acetamido-2-deoxymannopyranoside-containing saccharides using borate-saturated polyolic exclusion gels

A new separation method based on the combination of exclusion and ion exchange chromatography in borate buffer was developed. It allows semi-preparatory and preparatory separation of isobaric N-acylhexosamines (C-2 epimers) and corresponding methyl glycosides (anomers and tautomers). Three types of polyolic gels were tested for these separations. Ion-exchange HPLC was used as a rapid and reliable method for the quantification of the respective analytes. NMR studies of the interactions of N-acetylhexosamines with borate confirmed the importance of a proper stereochemical arrangement of acetamido sugars for their interactions with borate anions.