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Imaging and Analysis of Isomeric Unsaturated Lipids through Online Photochemical Derivatization of Carbon-Carbon Double Bonds*.

Publication ,  Journal Article
Unsihuay, D; Su, P; Hu, H; Qiu, J; Kuang, S; Li, Y; Sun, X; Dey, SK; Laskin, J
Published in: Angew Chem Int Ed Engl
March 29, 2021

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).

Duke Scholars

Published In

Angew Chem Int Ed Engl

DOI

EISSN

1521-3773

Publication Date

March 29, 2021

Volume

60

Issue

14

Start / End Page

7559 / 7563

Location

Germany

Related Subject Headings

  • Spectrometry, Mass, Electrospray Ionization
  • Singlet Oxygen
  • Photosensitizing Agents
  • Organic Chemistry
  • Lipids
  • Isotope Labeling
  • Isomerism
  • Hydrogen Peroxide
  • Carbon
  • 34 Chemical sciences
 

Citation

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Unsihuay, D., Su, P., Hu, H., Qiu, J., Kuang, S., Li, Y., … Laskin, J. (2021). Imaging and Analysis of Isomeric Unsaturated Lipids through Online Photochemical Derivatization of Carbon-Carbon Double Bonds*. Angew Chem Int Ed Engl, 60(14), 7559–7563. https://doi.org/10.1002/anie.202016734
Unsihuay, Daisy, Pei Su, Hang Hu, Jiamin Qiu, Shihuan Kuang, Yingju Li, Xiaofei Sun, Sudhansu K. Dey, and Julia Laskin. “Imaging and Analysis of Isomeric Unsaturated Lipids through Online Photochemical Derivatization of Carbon-Carbon Double Bonds*.Angew Chem Int Ed Engl 60, no. 14 (March 29, 2021): 7559–63. https://doi.org/10.1002/anie.202016734.
Unsihuay D, Su P, Hu H, Qiu J, Kuang S, Li Y, et al. Imaging and Analysis of Isomeric Unsaturated Lipids through Online Photochemical Derivatization of Carbon-Carbon Double Bonds*. Angew Chem Int Ed Engl. 2021 Mar 29;60(14):7559–63.
Unsihuay, Daisy, et al. “Imaging and Analysis of Isomeric Unsaturated Lipids through Online Photochemical Derivatization of Carbon-Carbon Double Bonds*.Angew Chem Int Ed Engl, vol. 60, no. 14, Mar. 2021, pp. 7559–63. Pubmed, doi:10.1002/anie.202016734.
Unsihuay D, Su P, Hu H, Qiu J, Kuang S, Li Y, Sun X, Dey SK, Laskin J. Imaging and Analysis of Isomeric Unsaturated Lipids through Online Photochemical Derivatization of Carbon-Carbon Double Bonds*. Angew Chem Int Ed Engl. 2021 Mar 29;60(14):7559–7563.
Journal cover image

Published In

Angew Chem Int Ed Engl

DOI

EISSN

1521-3773

Publication Date

March 29, 2021

Volume

60

Issue

14

Start / End Page

7559 / 7563

Location

Germany

Related Subject Headings

  • Spectrometry, Mass, Electrospray Ionization
  • Singlet Oxygen
  • Photosensitizing Agents
  • Organic Chemistry
  • Lipids
  • Isotope Labeling
  • Isomerism
  • Hydrogen Peroxide
  • Carbon
  • 34 Chemical sciences