Synthesis of novel dihydroceramides extracted from Porphyromonas gingivalis and the tissue and teeth of adult periodontal patients

Date of Completion

January 2004


Biology, Molecular|Chemistry, Organic|Health Sciences, Dentistry




Four novel dihydroceramides from Porphyromonas gingivalis were discovered by Dr. Frank Nichols, of the department of Periodontology at the University of Connecticut Health Center, to discover new virulence factors of the bacterium. Two putative dihydroceramides, N-[2-hydroxy-1-(hydroxymethyl)octadecyl]-3-hydroxy-13-methylhexadecanamide and N-[2-hydroxy-1-(hydroxymethyl)heptadecyl]-(2E)-heptadecenamide, were synthesized to identify their structures and confirm their presence as novel dihydroceramides in P. gingivalis. The components of the dihydroceramides, four sphinganines and two fatty acids, were also synthesized and compared with fractions obtained from P. gingivalis. The above data, the HPLC data, the biological data provided by Dr. Nichols, and the NMR data provided by Dr. Martha Morton, of the Department of Chemistry at the University of Connecticut, led to the identification of the structures of novel dihydroceramides from P. gingivalis that are responsible for deformations of fibroblasts in vitro. ^