ArticleChemical science2020
A visible-light activated [2 + 2] cycloaddition reaction enables pinpointing carbon-carbon double bonds in lipids.
Article in Chemical science, 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 11 papers.
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Who cites it
11 citing papers in PubMed, 39 citations in OpenAlex.
- Determination of double bond positions in unsaturated fatty acids by pre-column derivatization with dimethyl and dipyridyl disulfide followed by LC-SWATH-MS analysis.Analytical and bioanalytical chemistry · 2025Article
- Sample preparation for fatty acid analysis in biological samples with mass spectrometry-based strategies.Analytical and bioanalytical chemistry · 2024Review
- In situ droplet-based on-tissue chemical derivatization for lipid isomer characterization using LESA.Analytical and bioanalytical chemistry · 2023Article
- Chiral derivatization-enabled discrimination and on-tissue detection of proteinogenic amino acids by ion mobility mass spectrometry.Chemical science · 2022Article
- Novel Aza-Paternò-Büchi Reaction Allows Pinpointing Carbon-Carbon Double Bonds in Unsaturated Lipids by Higher Collisional Dissociation.Analytical chemistry · 2022Article
- Dual-resolving of positional and geometric isomers of C=C bonds via bifunctional photocycloaddition-photoisomerization reaction system.Nature communications · 2022Article
- Site-Specific Photochemical Reaction for Improved C=C Location Analysis of Unsaturated Lipids by Ultraviolet Photodissociation.Research (Washington, D.C.) · 2022Article
- Review of Recent Advances in Lipid Analysis of Biological Samples via Ambient Ionization Mass Spectrometry.Metabolites · 2021Review
- Advanced tandem mass spectrometry in metabolomics and lipidomics-methods and applications.Analytical and bioanalytical chemistry · 2021Review
- Quantification and molecular imaging of fatty acid isomers from complex biological samples by mass spectrometry.Chemical science · 2021Article
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Authors and funding
4 authors at 1 institution in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
The precise location of C[double bond, length as m-dash]C bonds in bioactive molecules is critical for a deep understanding of the relationship between their structures and biological roles. However, the traditional ultraviolet light-based approaches exhibited great limitations. Here, we discovered a new type of visible-light activated [2 + 2] cycloaddition of carbonyl with C[double bond, length as m-dash]C bonds. We found that carbonyl in anthraquinone showed great reactivities towards C[double bond, length as m-dash]C bonds in lipids to form oxetanes under the irradiation of visible-light. Combined with tandem mass spectrometry, this site-specific dissociation of oxetane enabled precisely locating the C[double bond, length as m-dash]C bonds in various kinds of monounsaturated and polyunsaturated lipids. The proof-of-concept applicability of this new type of [2 + 2] photocycloaddition was validated in the global identification of unsaturated lipids in a complex human serum sample. 86 monounsaturated and polyunsaturated lipids were identified with definitive positions of C[double bond, length as m-dash]C bonds, including phospholipids and fatty acids even with up to 6 C[double bond, length as m-dash]C bonds. This study provides new insights into both the photocycloaddition reactions and the structural lipidomics.
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Registered trials
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