title: ω-Azido fatty acids as probes to detect fatty acid biosynthesis, degradation, and modification.
abstract: FAs play a central role in the metabolism of almost all known cellular life forms. Although GC-MS is regarded as a standard method for FA analysis, other methods, such as HPLC/MS, are nowadays widespread but are rarely applied to FA analysis. Here we present azido-FAs as probes that can be used to study FA biosynthesis (elongation, desaturation) or degradation (β-oxidation) upon their uptake, activation, and metabolic conversion. These azido-FAs are readily accessible by chemical synthesis and their metabolic products can be easily detected after click-chemistry based derivatization with high sensitivity by HPLC/MS, contributing a powerful tool to FA analysis, and hence, lipid analysis in general.
authors.affiliation: Merck Stiftungsprofessur für Molekulare Biotechnologie, Fachbereich Biowissenschaften, Goethe Universität Frankfurt, 60438 Frankfurt am Main, Germany.
authors.forename: Alexander J
authors.initials: AJ
authors.lastname: Pérez
authors.affiliation: Merck Stiftungsprofessur für Molekulare Biotechnologie, Fachbereich Biowissenschaften, Goethe Universität Frankfurt, 60438 Frankfurt am Main, Germany.
authors.forename: Helge B
authors.initials: HB
authors.lastname: Bode
mesh_terms: D001386:Azides / Q000378:metabolism; D002851:Chromatography, High Pressure Liquid; D057930:Click Chemistry; D004926:Escherichia coli / Q000378:metabolism*; D005227:Fatty Acids / Q000096:biosynthesis* / Q000302:isolation & purification; D050155:Lipogenesis; D010084:Oxidation-Reduction; D021241:Spectrometry, Mass, Electrospray Ionization
chemical_list: D001386:Azides; D005227:Fatty Acids
keywords: S-azidoacyl-N-acetylcysteamine; azido-fatty acids; click-chemistry; cyclooctyne; fatty acid desaturation; fatty acid metabolism; strained promoted cycloadditon; β-oxidation