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Issue 27, 2020
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A visible-light activated [2 + 2] cycloaddition reaction enables pinpointing carbon–carbon double bonds in lipids

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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.

Graphical abstract: A visible-light activated [2 + 2] cycloaddition reaction enables pinpointing carbon–carbon double bonds in lipids

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Supplementary files

Article information


Submitted
26 Feb 2020
Accepted
20 Jun 2020
First published
22 Jun 2020

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2020,11, 7244-7251
Article type
Edge Article

A visible-light activated [2 + 2] cycloaddition reaction enables pinpointing carbon–carbon double bonds in lipids

G. Feng, Y. Hao, L. Wu and S. Chen, Chem. Sci., 2020, 11, 7244
DOI: 10.1039/D0SC01149E

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    [Original citation] - Published by The Royal Society of Chemistry (RSC) on behalf of the European Society for Photobiology, the European Photochemistry Association, and RSC.
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