Premium
Imaging and Analysis of Isomeric Unsaturated Lipids through Online Photochemical Derivatization of Carbon–Carbon Double Bonds **
Author(s) -
Unsihuay Daisy,
Su Pei,
Hu Hang,
Qiu Jiamin,
Kuang Shihuan,
Li Yingju,
Sun Xiaofei,
Dey Sudhansu K.,
Laskin Julia
Publication year - 2021
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.202016734
Subject(s) - chemistry , double bond , derivatization , photochemistry , lipidomics , lipidome , photosensitizer , mass spectrometry , electrospray ionization , singlet oxygen , fragmentation (computing) , chromatography , oxygen , organic chemistry , biochemistry , computer science , operating system
Unraveling the complexity of the lipidome requires the development of novel approaches for the structural characterization of lipid species with isomer‐level discrimination. Herein, we introduce an online photochemical approach for lipid isomer identification through selective derivatization of double bonds by reaction with singlet oxygen. Lipid hydroperoxide products are generated promptly after laser irradiation. Fragmentation of these species in a mass spectrometer produces diagnostic fragments revealing the C=C locations in the unreacted lipids. This approach uses an inexpensive light source and photosensitizer making it easy to incorporate into any lipidomics workflow. We demonstrate the utility of this approach for the shotgun profiling of C=C locations in different lipid classes present in tissue extracts using electrospray ionization (ESI) and ambient imaging of lipid species differing only by the location of C=C bonds using nanospray desorption electrospray ionization (nano‐DESI).