Synthesis and stereochemical evaluation of bioactive ceramides from the dental pathogen Porphyromonas gingivalis

ORGN 671

Amber Onorato, Amber.Onorato@huskymail.uconn.edu1, Frank Nichols, nichols@nso.uchc.edu2, and Michael B. Smith, michael.smith@uconn.edu1. (1) Department of Chemistry, University of Connecticut, 55 N. Eagleville Rd., Storrs, CT 06269-3060, (2) Department of Periondontology, University of Connecticut Health Center, 263 Farmington Avenue, Farmington, CT 06030
Porphyromonas gingivalis is a suspected periodontal pathogen that produces several novel ceramides, with biological activity ranging from pro-inflammatory agents, to compounds that induce bone degeneration, to compounds that induce multiple sclerosis symptoms in mice. Spectral analysis of mixtures of the extracts suggested these lipids are ceramides that are characterized by isobranched, odd carbon chains, and b-hydroxyl functionality. We have synthesized several of these putative compounds and verified their presence in the complex lipid mixture. Apart form the synthesis and verification of the structure, our work is focused on determining the absolute and relative stereochemistry of the most active ceramides.

 

Total Synthesis of Complex Molecules
8:00 AM-12:00 PM, Wednesday, August 22, 2007 BCEC -- 258A, Oral

Division of Organic Chemistry

The 234th ACS National Meeting, Boston, MA, August 19-23, 2007