A straightforward route to sphinganine-containing alpha-galactosylceramides

ORGN 671

Amy R. Howell, amy.howell@uconn.edu and Rachel M Ndonye, rndonye@yahoo.com. Department of Chemistry, University of Connecticut, Storrs, CT 06269
The alpha-galactosylceramide KRN 7000 has been identified as a potent stimulatory agent for immunological processes mediated by CD-1 antigen presenting proteins. OCH is an alpha-galactosylceramide which has shown to induce autoimmune T cells leading to suppression of experimental autoimmune encephalomyelitis (EAE). The aminodiol analogs 1b and 2b of KRN7000 and OCH have been shown to be nearly potent as the parent compounds. We have developed a novel approach to the aminodiol portion of alpha-galactosylceramides. The application of this methodology to the synthesis of 1b and 2b and results of biological assay will be discussed.

 

New Reactions and Methodology
1:00 PM-5:00 PM, Wednesday, 16 March 2005 Convention Center -- Ballroom 20 C-D, Oral

Division of Organic Chemistry

The 229th ACS National Meeting, in San Diego, CA, March 13-17, 2005