The antituberculosis, antitumor, multibranched dodecafuranoarabinan of Mycobacterium species has been assembled from a single n-pentenylfuranoside source.
An n-pentenyl furanosyl-1,2-orthoester can function as a donor or be rearranged leading to an n-pentenyl furanoside acceptor which is glycosylated by its progenitor, regioselectively or doubly, thereby enabling rapid fabrication of a multibranched dodecasaccharide, known to possess a wide variety of biological interactions.
Lu
Jun
J
Natural Products and Glycotechnology Research Institute, Inc., 4118 Swarthmore Road, Durham, NC 27707, USA.
Fraser-Reid
Bert
B
D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry; D000995:Antitubercular Agents / Q000138:chemical synthesis* / Q000737:chemistry; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000737:chemistry; D002236:Carbohydrate Conformation; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D008969:Molecular Sequence Data; D009161:Mycobacterium / Q000737:chemistry* / Q000145:classification; D010429:Pentoses / Q000737:chemistry; D011134:Polysaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D013045:Species Specificity; D013237:Stereoisomerism
D000970:Antineoplastic Agents; D000995:Antitubercular Agents; D019086:Bridged Bicyclo Compounds, Heterocyclic; D005663:Furans; D010429:Pentoses; D011134:Polysaccharides