Synthesis of arabinofuranose-containing oligosaccharide fragments of mycobacterial lipoarabinomannan

CARB 52

Ruel C. Nacario, rnacario@ualberta.ca, Department of Chemistry and The Alberta Ingenuity Centre for Carbohydrate Science, University of Alberta, Gunning-Lemieux Chemistry Centre, 11227 Saskatchewan Drive, Edmonton, AB T6G 2G2, Canada and Todd L. Lowary, tlowary@ualberta.ca, Department of Chemistry and Alberta Ingenuity Centre for Carbohydrate Science, University of Alberta, Gunning-Lemieux Chemistry Centre, Edmonton, AB T6G 2G2, Canada.

The resurgence of mycobacterial tuberculosis (TB) is attributed to the appearance of strains of the pathogen resistant to current anti-TB drugs.  This has spurred interest in the development of new chemotherapeutic agents against TB as well as new vaccines for the prevention of the disease.  The nonreducing ends of the mycobacterial cell wall polysaccharide lipoarabinomannan is terminated with a hexasaccharide motif (1) thought to be involved in immunological events associated with mycobacterial infection and is also shown to be recognized by an antibody generated against Mycobacterium leprae LAM [1].  In an effort to provide large amounts of this hexasaccharide for the development of a viable hapten for vaccine generation, we have investigated a new route to this motif [2,3].  In the route reported here, the key step is a stereoselective glycosylation between disaccharide 2 and acceptor 3, which provides a pentasaccharide that can be further elaborated to 1.

 

 

General Posters
8:00 PM-10:00 PM, Tuesday, 12 September 2006 Moscone Center -- Hall D, Poster

Division of Carbohydrate Chemistry

The 232nd ACS National Meeting, San Francisco, CA, September 10-14, 2006