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Dihydroxylated E,E,Z-docosatrienes. An overview of their synthesis and biological significance
Affiliation:1. Instituto de Investigação e Inovação em Saúde, Universidade do Porto, Rua Alfredo Allen, 208, 4200-135 Porto, Portugal;2. IBMC, Instituto de Biologia Molecular e Celular, Porto, Portugal;3. ICBAS, Instituto de Ciências Biomédicas Abel Salazar, Departamento de Biologia Molecular, Universidade do Porto, Rua de Jorge Viterbo Ferreira, 228, 4050-313 Porto, Portugal;1. Institute of Health and Environment, Seoul National University, Seoul, Republic of Korea;2. Ajou University School of Medicine, Suwon, Republic of Korea;3. Novartis Pharma AG, Switzerland;4. Novartis S.A., Buenos Aires, Argentina
Abstract:Dihydroxylated E,E,Z-docosatrienes are acyclic lipoxygenase metabolites of 22-carbon atom polyunsaturated fatty acids (PUFAs) containing a conjugated E,E,Z-triene flanked by two secondary allylic alcohols. The two main metabolites, protectin D1 (PD1) and its regioisomer maresin 1 (MaR1), were shown to be actively involved in the resolution and more specifically the termination of the inflammation process.Studies directed at the synthesis of E,E,Z-docosatrienes have been undertaken to resolve stereochemical ambiguities, and provide standards for biological evaluation and reference samples for in-vivo detection and lipidomic analyses.In this review we provide a brief update of the literature on the biological significance of E,E,Z-docosatrienes and the role that synthetic organic chemists has played in the development of these lipids, providing an overview and comparison of the different strategies employed to access synthetic E,E,Z-docosatriene standards.
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