title: Convergent synthesis of a deuterium-labeled serine dipeptide lipid for analysis of biological samples.
abstract: Bacterial serine dipeptide lipids are known to promote inflammatory processes and are detected in human tissues associated with periodontal disease or atherosclerosis. Accurate quantification of bacterial serine lipid, specifically lipid 654 [((S)-15-methyl-3-((13-methyltetradecanoyl)oxy)hexadecanoyl)glycyl-l-serine, (3S)-l-serine] isolated from Porphyromonas gingivalis, in biological samples requires the preparation of a stable isotope internal standard for sample supplementation and subsequent mass spectrometric analysis. This report describes the convergent synthesis of a deuterium-substituted serine dipeptide lipid, which is an isotopically labeled homologue that represents a dominant form of serine dipeptide lipid recovered in bacteria.
authors.affiliation: Department of Chemistry, The University of Connecticut, Storrs, CT, USA.
authors.forename: Christopher
authors.initials: C
authors.lastname: Dietz
authors.affiliation: Department of Immunology, The University of Connecticut Health Center, Farmington, CT, USA.
authors.forename: Robert B
authors.initials: RB
authors.lastname: Clark
authors.affiliation: Division of Periodontology, The University of Connecticut Health Center, Farmington, CT, USA.
authors.forename: Frank C
authors.initials: FC
authors.lastname: Nichols
authors.affiliation: Department of Chemistry, The University of Connecticut, Storrs, CT, USA.
authors.forename: Michael B
authors.identifier: 0000-0002-8436-4471
authors.initials: MB
authors.lastname: Smith
mesh_terms: D060326:Chemistry Techniques, Synthetic; D003903:Deuterium / Q000737:chemistry*; D004151:Dipeptides / Q000737:chemistry*; D007553:Isotope Labeling; D050356:Lipid Metabolism; D008055:Lipids / Q000138:chemical synthesis* / Q000737:chemistry*; D055666:Lipopeptides / Q000138:chemical synthesis* / Q000737:chemistry*; D016966:Porphyromonas gingivalis / Q000378:metabolism; D012694:Serine / Q000737:chemistry*; D013237:Stereoisomerism; D037521:Virulence Factors / Q000138:chemical synthesis* / Q000737:chemistry*
chemical_list: D004151:Dipeptides; D008055:Lipids; D055666:Lipopeptides; D037521:Virulence Factors; C000625727:serine dipeptide lipid 654; D012694:Serine; D003903:Deuterium
keywords: bacteria; ddipeptides; lipids; peridontal disease; synthesis