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Issue 23, 2007
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Structural confirmation of the dihydrosphinganine and fatty acid constituents of the dental pathogen Porphyromonas gingivalis

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Abstract

Porphyromonas gingivalis, a recognized periodontal pathogen, is a source of sphinganine bases, fatty acids, free ceramides as well as complex lipids that potentiate interleukin-1b-mediated secretory responses in gingival fibroblasts. The purpose of this study is the structural verification of the sphinganine bases and fatty acids that had been proposed as major components of the complex lipids found in P. gingivalis. The putative C17, C18, and C19 sphinganine bases were prepared from Garner's aldehyde (1) or from a protected serine Weinreb's amide (2). We confirmed that isobranched sphinganine bases are the major structural feature of the ceramides observed from P. gingivalis. We also prepared a C17 unsaturated fatty acid, along with an isobranched C17 3-hydroxy fatty acid, and determined that the major component of the active lipids was the latter.

Graphical abstract: Structural confirmation of the dihydrosphinganine and fatty acid constituents of the dental pathogen Porphyromonas gingivalis

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Publication details

The article was received on 17 Aug 2007, accepted on 26 Sep 2007 and first published on 29 Oct 2007


Article type: Paper
DOI: 10.1039/B712707C
Citation: Org. Biomol. Chem., 2007,5, 3826-3833
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    Structural confirmation of the dihydrosphinganine and fatty acid constituents of the dental pathogen Porphyromonas gingivalis

    J. Mun, A. Onorato, F. C. Nichols, M. D. Morton, A. I. Saleh, M. Welzel and M. B. Smith, Org. Biomol. Chem., 2007, 5, 3826
    DOI: 10.1039/B712707C

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