The first total synthesis of a highly branched arabinofuranosyl hexasaccharide found at the nonreducing termini of mycobacterial arabinogalactan and lipoarabinomannan.
[reaction--see text] The first total synthesis of the arabinofuranosyl hexasaccharide present at the nonreducing termini of mycobacterial arabinogalactan and lipoarabinomannan is reported. The oligosaccharide was prepared as its methyl glycoside via a route that is both highly efficient and convergent. Addition of two beta-D-arabinofuranosyl residues simultaneously in high yield and with excellent stereocontrol was the key step of the synthesis.
D'Souza
F W
FW
Department of Chemistry, The Ohio State University, Columbus, Ohio 43210, USA.
Lowary
T L
TL
D001089:Arabinose; D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D005685:Galactans / Q000737:chemistry*; D007202:Indicators and Reagents; D008070:Lipopolysaccharides / Q000737:chemistry*; D008969:Molecular Sequence Data; D009161:Mycobacterium / Q000737:chemistry*; D009844:Oligosaccharides / Q000138:chemical synthesis* / Q000737:chemistry*; D011135:Polysaccharides, Bacterial / Q000737:chemistry*; D013237:Stereoisomerism
D005685:Galactans; D007202:Indicators and Reagents; D008070:Lipopolysaccharides; D009844:Oligosaccharides; D011135:Polysaccharides, Bacterial; C050016:lipoarabinomannan; D001089:Arabinose; C005653:arabinogalactan