Unsaturated RO radicals from the ozonolysis of cyclodienes can readily undergo an endo-cyclization step under atmospheric conditions forming a new ring-containing RO radical after further O addition. This path represents an extension of the atmospheric autoxidation scheme forming highly oxidized multifunctional organic compounds (HOMs). HOMs play an important role for Earth's organic aerosol burden.
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http://dx.doi.org/10.1039/c7cc01350g | DOI Listing |
Anal Chem
January 2025
The Institute for Advanced Studies, Wuhan University, Wuhan, Hubei 430072, China.
The position and configuration of the C═C bond have a significant impact on the spatial conformation of unsaturated lipids, which subsequently affects their biological functions. Double bond isomerization of lipids is an important mechanism of bacterial stress response, but its in-depth mechanistic study still lacks effective analytical tools. Here, we developed a visible-light-activated dual-pathway reaction system that enables simultaneous [2 + 2] cycloaddition and catalytic - isomerization of the C═C bond of unsaturated lipids via directly excited anthraquinone radicals.
View Article and Find Full Text PDFJ Food Sci
December 2024
College of Food Science and Engineering, Wuhan Polytechnic University, Wuhan, China.
Excessive oxidation of protein and lipids in pork leads to quality degradation and loss of nutrients. Kappa-selenocarrageenan (Se-K) can not only be used as a selenium enhancer but also as an antioxidant. To explore potential antioxidants that could be applied to pork, the effect of Se-K on myofibrillar protein (MP) and lipid oxidation was investigated.
View Article and Find Full Text PDFJ Org Chem
December 2024
Henan Key Laboratory of Nanocomposites and Applications; Institute of Nanostructured Functional Materials, Huanghe Science and Technology College, Zhengzhou 450006, China.
A photoredox-catalyzed aminolactonization of unsaturated carboxylic acids was achieved using -aminopyridinium salts as the amino radical precursor. The transformation features mild conditions and a remarkably broad substrate scope, offering an efficient approach to construct a wide range of 4-sulfonamino 3,4-dihydroisocoumarins. Mechanistic studies indicate that the reaction proceeds via a distinctive -aminopyridinium salt-promoted electrophilic amination of 2-styrylbenzoic acids.
View Article and Find Full Text PDFRedox Biol
December 2024
Department of Chemistry, Brown University, Providence, RI, 02912, USA. Electronic address:
Thiyl radicals are important reactive sulfur species and can cause cis to trans isomerization on unsaturated fatty acids. However, biocompatible strategies for the controlled generation of thiyl radicals are still lacking. In this work, we report the study of a series of naphthacyl-derived thioethers as photo-triggered thiyl radical precursors.
View Article and Find Full Text PDFBeilstein J Org Chem
December 2024
Department of Chemical and Geological Sciences, University of Cagliari, S.S. 554, bivio per Sestu, 09042 Monserrato (CA), Italy.
The rising popularity of bioconjugate therapeutics has led to growing interest in late-stage functionalization (LSF) of peptide scaffolds. α,β-Unsaturated amino acids like dehydroalanine (Dha) derivatives have emerged as particularly useful structures, as the electron-deficient olefin moiety can engage in late-stage functionalization reactions, like a Giese-type reaction. Cheap and widely available building blocks like organohalides can be converted into alkyl radicals by means of photoinduced silane-mediated halogen-atom transfer (XAT) to offer a mild and straightforward methodology of alkylation.
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