Synthesis of oligosaccharides of motifs D and E of arabinogalactan present in Mycobacterium tuberculosis.
Syntheses of the ethyl glycosides of 5-O-(beta-D-galactofuranosyl)-beta-D-galactofuranose and 5-O-(alpha-D-arabinofuranosyl)-6-O-(beta-D-galactofuranosyl)-beta-D-galactofuranose present in motifs D and E of Mycobacterium tuberculosis arabinogalactan, respectively, have been presented. The pentenyl-mediated O-glycosylation reaction was utilized to obtain the disaccharide of motif D. The first coupling reaction to prepare the inner disaccharide portion of motif E was accomplished by trichloroacetamidate method while the installation of the terminal sugar by pentenyl glycosylation approach was successful.
Gurjar
M K
MK
National Chemical Laboratory, Pune 411 008, India. gurjar@dalton.ncl.res.in
Reddy
L K
LK
Hotha
S
S
D002240:Carbohydrate Sequence; D005685:Galactans / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D009169:Mycobacterium tuberculosis / Q000737:chemistry*; D009844:Oligosaccharides / Q000138:chemical synthesis* / Q000737:chemistry
D005685:Galactans; D009844:Oligosaccharides; C005653:arabinogalactan