An On‐Tissue Paternò–Büchi Reaction for Localization of Carbon–Carbon Double Bonds in Phospholipids and Glycolipids by Matrix‐Assisted Laser‐Desorption–Ionization Mass‐Spectrometry Imaging

Matrix‐assisted laser desorption ionization mass spectrometry imaging (MALDI‐MSI) visualizes the distribution of phospho‐ and glycolipids in tissue sections. However, C=C double‐bond (db) positional isomers generally cannot be distinguished. Now an on‐tissue Paternò–Büchi (PB) derivatization procedu...

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Bibliographic Details
Published in:Angewandte Chemie 2018-09, Vol.130 (37), p.12268-12272
Main Authors: Bednařík, Antonín, Bölsker, Stefan, Soltwisch, Jens, Dreisewerd, Klaus
Format: Article
Language:English
Subjects:
Benzaldehyde
Brain
Carbon
Cerebellum
Chemistry
Desorption
Glycolipids
Glycosphingolipids
Ion pairs
Ionization
Ions
Isomers
Lasers
Lecithin
Localization
MALDI-MS-Bildgebung
Mass spectrometry
Mass spectroscopy
Neuroimaging
Paternò-Büchi-Reaktion
Phosphatidylcholine
Phosphatidylserine
Phospholipide
Phospholipids
Photochemie
Reagents
Scientific imaging
Spectroscopy
Stellungsisomere
Substantia grisea
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Summary:Matrix‐assisted laser desorption ionization mass spectrometry imaging (MALDI‐MSI) visualizes the distribution of phospho‐ and glycolipids in tissue sections. However, C=C double‐bond (db) positional isomers generally cannot be distinguished. Now an on‐tissue Paternò–Büchi (PB) derivatization procedure that exploits benzaldehyde as a MALDI‐MSI‐compatible reagent is introduced. Laser‐induced postionization (MALDI‐2) was used to boost the yields of protonated PB products. Collision‐induced dissociation of these species generated characteristic ion pairs, indicative of C=C position, for numerous singly and polyunsaturated phospholipids and glycosphingolipids in mouse brain tissue. Several db‐positional isomers of phosphatidylcholine and phosphatidylserine species were expressed with highly differential levels in the white and gray matter areas of cerebellum. Our PB‐MALDI‐MS/MS procedure could help to better understand the physiological role of these db‐positional isomers. MALDI‐MS‐Verteilungskarten der C=C‐Stellungsisomere von Phospho‐ und Glykolipiden werden durch eine Offline‐Paternò‐Büchi‐Photoderivatisierung mit Benzaldehyd zugänglich. Verschiedene Isomere zeigen eine charakteristische Verteilung im Maus‐Kleinhirn, die auf komplexe biochemische Prozesse mit derzeit noch unbekanntem Hintergrund hindeutet.
ISSN:0044-8249
1521-3757
DOI:10.1002/ange.201806635