ArticleJournal of natural products2015
Synthesis of the 16S,17S-Epoxyprotectin Intermediate in the Biosynthesis of Protectins by Human Macrophages.
Article in Journal of natural products, 2015. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 25 papers.
What it found
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Who cites it
25 citing papers in PubMed.
- Biosynthesis and analytics of specialized pro-resolving mediators: facts and faults.Journal of lipid research · 2026Review
- The Multifaceted Role of Neuroprotectin D1: Physiological, Pathophysiological, and Pharmacological Insights in Neurodegenerative Diseases.Current neuropharmacology · 2025Review
- Biotransformation of docosahexaenoic acid into 10R,17S-dihydroxydocosahexaenoic acid as protectin DX 10-epimer by serial reactions of arachidonate 8R- and 15S-lipoxygenases.World journal of microbiology & biotechnology · 2024Article
- Stereochemistry and functions of the new cysteinyl-resolvin, 4S,5R-RCTR1, in efferocytosis and erythrophagocytosis of human senescent erythrocytes.American journal of hematology · 2023Article
- Resolvins and cysteinyl-containing pro-resolving mediators activate resolution of infectious inflammation and tissue regeneration.Prostaglandins & other lipid mediators · 2023Review
- Protectins: Their biosynthesis, metabolism and structure-functions.Biochemical pharmacology · 2022Review
- A newly synthesized 17-epi-NeuroProtectin D1/17-epi-Protectin D1: Authentication and functional regulation of Inflammation-Resolution.Biochemical pharmacology · 2022Article
- Article
- A new synthetic protectin D1 analog 3-oxa-PD1Organic & biomolecular chemistry · 2021Article
- The First Total Synthesis of the Lipid Mediator PD2Journal of natural products · 2020Article
- The Biosynthesis of Enzymatically Oxidized Lipids.Frontiers in endocrinology · 2020Review
- Targeting biosynthetic networks of the proinflammatory and proresolving lipid metabolome.FASEB journal : official publication of the Federation of American Societies for Experimental Biology · 2019Article
- Resolving Inflammation: Synthesis, Configurational Assignment, and Biological Evaluations of RvD1Chemistry (Weinheim an der Bergstrasse, Germany) · 2019Article
- Metal-Free Synthesis of Functionalized Tetrasubstituted Alkenes by Three-Component Reaction of Alkynes, Iodine, and Sodium Sulfinates.ACS omega · 2018Article
- Synthesis of protectin D1 analogs: novel pro-resolution and radiotracer agents.Organic & biomolecular chemistry · 2018Article
- PDCell chemical biology · 2018Article
- The Protectin Family of Specialized Pro-resolving Mediators: Potent Immunoresolvents Enabling Innovative Approaches to Target Obesity and Diabetes.Frontiers in pharmacology · 2018Review
- Structural elucidation and physiologic functions of specialized pro-resolving mediators and their receptors.Molecular aspects of medicine · 2017Review
- Discovery of specialized pro-resolving mediators marks the dawn of resolution physiology and pharmacology.Molecular aspects of medicine · 2017Review
- The novel lipid mediator PD1Prostaglandins & other lipid mediators · 2017Review
Corrections and comments
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Authors and funding
7 authors.
Funding
Abstract
The n-3 polyunsaturated fatty acids act as substrates during the resolution phase of acute inflammation for the biosynthesis of specialized pro-resolving lipid mediators. One premier example is the C22-dihydroxy-polyunsaturated fatty acid protectin D1 (1). The human 15-lipoxygenase type I, via stereoselective processes and with docosahexaenoic acid as the substrate, enables the formation of this specialized pro-resolving lipid mediator. Herein, based on results from LC/MS-MS metabololipidomics, support is presented for the apprehended biosynthesis of 1 in human macrophages occurring via the intermediate 16S,17S-epoxyprotectin (5). Stereochemically pure 5 was obtained using the Katsuki-Sharpless epoxidation protocol, establishing the chirality at the C16 and C17 atoms, one Z-selective reduction, and E- and Z-stereoselective Wittig reactions. In addition, information on the nonenzymatic aqueous hydrolysis products and the half-life of 16S,17S-epoxyprotectin (5) is presented.
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Registered trials
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