Back to Search Start Over

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.

Authors :
Pragani R
Stallforth P
Seeberger PH
Source :
Organic letters [Org Lett] 2010 Apr 02; Vol. 12 (7), pp. 1624-7.
Publication Year :
2010

Abstract

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.

Details

Language :
English
ISSN :
1523-7052
Volume :
12
Issue :
7
Database :
MEDLINE
Journal :
Organic letters
Publication Type :
Academic Journal
Accession number :
20196573
Full Text :
https://doi.org/10.1021/ol1003912