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.

Keywords: S-azidoacyl-N-acetylcysteamine; azido-fatty acids; click-chemistry; cyclooctyne; fatty acid desaturation; fatty acid metabolism; strained promoted cycloadditon; β-oxidation.