Bioactive lipids from Porphyromonas gingivalis

ORGN 668

Michael B. Smith, michael.smith@uconn.edu1, Frank Nichols, nichols@nso.uchc.edu2, Amber Onorato, Amber.Onorato@huskymail.uconn.edu1, and Morgan Welzel1. (1) Department of Chemistry, University of Connecticut, 55 N. Eagleville Road, Storrs, CT 06269-3060, (2) Department of Periondontology, University of Connecticut Health Center, 263 Farmington Avenue, Farmington, CT 06030
The dental pathogen Porphyromonas gingivalis produces a series of lipids, believed to be ceramides with fascinating biological activity. One fraction acts as an inflammatory agent, stimulates osteoclast activity, bypassing the RANK ligand, and suppresses monocyte formation. Another fraction leads to multiple-sclerosis symptoms in mice at very low dosages. In both cases, the ceramides have odd carbon chains, isobranching, beta-hydroxy fatty acid units, and phosphorus head groups. Synthesis and structural verification of these compounds as synthetic standards involves a convergent strategy based on Garner's aldehyde.
 

Lipids, Nucleotides, and Mimetics
1:00 PM-4:40 PM, Wednesday, 13 September 2006 Moscone Center -- Room 131, Oral

Division of Organic Chemistry

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