De novo synthesis of a 2-acetamido-4-amino-2,4,6-trideoxy-D-galactose (AAT) building block for the preparation of a Bacteroides fragilis A1 polysaccharide fragment.
Zwitterionic polysaccharides (ZPSs) are potent T-cell activators that naturally occur on the cell surface of bacteria and show potential as immunostimulatory agents. An unusual, yet important component of many ZPSs is 2-acetamido-4-amino-2,4,6-trideoxy-D-galactose (AAT). AAT building block 2 was prepared via a de novo synthesis from N-Cbz-L-threonine 5. Furthermore, building block 2 was used to synthesize disaccharide 15 that constitutes a fragment of zwitterionic polysaccharide A1 (PS A1) found in Bacteroides fragilis.
Pragani
Rajan
R
Max-Planck-Institute of Colloids and Interfaces, Department of Biomolecular Systems, Am Muhlenberg 1, 14476 Potsdam, Germany.
Stallforth
Pierre
P
Seeberger
Peter H
PH
D001441:Bacteroides fragilis / Q000737:chemistry*; D005690:Galactose / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D008968:Molecular Conformation; D011135:Polysaccharides, Bacterial / Q000737:chemistry*; D013237:Stereoisomerism
C550267:2-acetamido-4-amino-2,4,6-trideoxy-D-galactose; D011135:Polysaccharides, Bacterial; D005690:Galactose