Arabinofuranosides from mycobacteria: synthesis of a highly branched hexasaccharide and related fragments containing beta-arabinofuranosyl residues.
The synthesis of 11 oligosaccharides (4-14) containing beta-arabinofuranosyl residues is reported. The glycans are all fragments of two polysaccharides, arabinogalactan and lipoarabinomannan, which are found in the cell wall complex of mycobacteria. In the preparation of the targets, the key step was a low-temperature glycosylation reaction that installed the beta-arabinofuranosyl residues with good to excellent stereocontrol.
Yin
Haifeng
H
Department of Chemistry, The Ohio State University, 100 West 18th Avenue, Columbus, Ohio 43210, USA.
D'Souza
Francis W
FW
Lowary
Todd L
TL
D001087:Arabinonucleosides / Q000138:chemical synthesis / Q000737:chemistry / Q000302:isolation & purification*; D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D005663:Furans / Q000138:chemical synthesis / Q000737:chemistry / Q000302:isolation & purification*; D008969:Molecular Sequence Data; D009161:Mycobacterium / Q000737:chemistry*; D009844:Oligosaccharides / Q000138:chemical synthesis*
D001087:Arabinonucleosides; D005663:Furans; D009844:Oligosaccharides