Progress towards the preparation of a vancomycin derivative containing a septanose residue at the vancosamine position

CARB 55

Nicole L. Snyder, nsnyderl@wellesley.edu, Meghan F. Hogan, mhogan1@wellesley.edu, and Adelaide M. de Guillebon, adeguill@wellesley.edu. Department of Chemistry, Wellesley College, 106 Central Street, Wellesley, MA 02481
The glycopeptide antibiotic vancomycin (A), once considered the antibiotic of last resort, has seen the development of many strains of resistant bacteria over the past twenty years. Several attempts to overcome this resistance have focused on functionalizing the amino group of a peripheral carbohydrate component of vancomycin, known as the vancosamine sugar. Here, we present recent progress towards the development of an entirely new derivative of vancomycin that incorporates a septanose residue at the vancosamine position (B). The septanose residue is the result of a formal one carbon homologation of the natural vancosamine sugar. Vancomycin derivative B shows promise as a potential analog that can be used combat vancomycin resistant strains of bacteria.

 

General Posters
6:00 PM-8:00 PM, Tuesday, 28 March 2006 Georgia World Congress Center -- Ex. Hall B4, Poster

Sci-Mix
8:00 PM-10:00 PM, Monday, 27 March 2006 Georgia World Congress Center -- Ex. Hall B4, Sci-Mix

Division of Carbohydrate Chemistry

The 231st ACS National Meeting, Atlanta, GA, March 26-30, 2006