Access the full text.
Sign up today, get DeepDyve free for 14 days.
N. Bazan, V. Marcheselli, Kasie Cole-Edwards (2005)
Brain Response to Injury and NeurodegenerationAnnals of the New York Academy of Sciences, 1053
J. Hollyfield (2010)
Age-related macular degeneration: the molecular link between oxidative damage, tissue-specific inflammation and outer retinal disease: the Proctor lecture.Investigative ophthalmology & visual science, 51 3
(2004)
Neuroprotectin D1: a docosahexaenoic acid-derived docosatriene protects human retinal pigment epithelial cells from oxidative stress.Proceedings of the National Academy of Sciences of the United States of America, 101 22
R. Uauy, E. Birch, D. Birch, P. Peirano (1992)
Visual and brain function measurements in studies of n-3 fatty acid requirements of infants.The Journal of pediatrics, 120 4 Pt 2
C. Oger, L. Balas, T. Durand, J. Galano (2013)
Are alkyne reductions chemo-, regio-, and stereoselective enough to provide pure (Z)-olefins in polyfunctionalized bioactive molecules?Chemical reviews, 113 3
Baldip Kang, R. Britton (2007)
A general method for the synthesis of nonracemic trans-epoxides: concise syntheses of trans-epoxide-containing insect sex pheromones.Organic letters, 9 24
ESIÀ): m/z calcd for C 22 H 29 D 2 O 2 :3 31.2575 [MÀH] À ;f ound:3 31.2574;H PLC (column:B ridge BEH (C 18 ); particle size:2 .5 mm; dimensions:2 .1 100 mm;w ater/MeOH, 20:80;i socratic flow
C. Schneider, K. Tallman, N. Porter, A. Brash (2001)
Two Distinct Pathways of Formation of 4-HydroxynonenalThe Journal of Biological Chemistry, 276
B. Gugiu, C. Mesaros, Mingjiang Sun, X. Gu, J. Crabb, R. Salomon (2006)
Identification of oxidatively truncated ethanolamine phospholipids in retina and their generation from polyunsaturated phosphatidylethanolamines.Chemical research in toxicology, 19 2
Gerald Kohl, R. Rudolph, H. Pritzkow, M. Enders (2005)
Catalytic C-H Activation of Hydrocarbons by Rhodium(I) and Iridium(I) Complexes with Hemilabile Quinolyl-Cp LigandsOrganometallics, 24
G. Bannenberg, Chia Nan, A. Ariel, M. Arita, Eric Tjonahen, K. Gotlinger, Song Hong, C. Serhan (2005)
Molecular Circuits of Resolution: Formation and Actions of Resolvins and Protectins1The Journal of Immunology, 174
Feng Li, L. Marchette, R. Brush, M. Elliott, Y. Le, Kimberly Henry, Ashley Anderson, Chao Zhao, Xufang Sun, Kang Zhang, R. Anderson (2009)
DHA does not protect ELOVL4 transgenic mice from retinal degenerationMolecular Vision, 15
Ullrich Jahn, Jean-Marie Galano, T. Durand (2008)
Jenseits von Prostaglandinen – Chemie und Biologie radikalisch gebildeter cyclischer oxygenierter Metabolite von mehrfach ungesättigten FettsäurenAngewandte Chemie, 120
A. Guy, C. Oger, J. Heppekausen, C. Signorini, C. Felice, A. Fürstner, T. Durand, J. Galano (2014)
Oxygenated metabolites of n-3 polyunsaturated fatty acids as potential oxidative stress biomarkers: total synthesis of 8-F3t-IsoP, 10-F4t-NeuroP and [D4]-10-F4t-NeuroP.Chemistry, 20 21
K. Bowen, W. Harris, P. Kris-Etherton (2016)
Omega-3 Fatty Acids and Cardiovascular Disease: Are There Benefits?Current Treatment Options in Cardiovascular Medicine, 18
(2014)
Centre Hospitalier Universitaire Montpellier,I nstitutN ational de la Sante et de la RechercheM edical
L. Balas, T. Durand (2016)
Dihydroxylated E,E,Z-docosatrienes. An overview of their synthesis and biological significance.Progress in lipid research, 61
M. Prechtl, M. Hölscher, Yehoshoa Ben‐David, N. Theyssen, Rebekka Loschen, D. Milstein, W. Leitner (2007)
H/D exchange at aromatic and heteroaromatic hydrocarbons using D2O as the deuterium source and ruthenium dihydrogen complexes as the catalyst.Angewandte Chemie, 46 13
Rosa Corberán, M. Sanaú, E. Peris (2006)
Highly stable Cp*-Ir(III) complexes with N-heterocyclic carbene ligands as C-H activation catalysts for the deuteration of organic molecules.Journal of the American Chemical Society, 128 12
Cathleen Yung, M. Skaddan, R. Bergman (2004)
Stoichiometric and catalytic H/D incorporation by cationic iridium complexes: a common monohydrido-iridium intermediate.Journal of the American Chemical Society, 126 40
N. Bazan, J. Calandria, C. Serhan (2010)
Rescue and repair during photoreceptor cell renewal mediated by docosahexaenoic acid-derived neuroprotectin D1Journal of Lipid Research, 51
Shauna Hill, K. Hirano, Vadim Shmanai, B. Marbois, Dragoslav Vidovic, A. Bekish, B. Kay, Vincent Tse, Jonathan Fine, Catherine Clarke, M. Shchepinov (2011)
Isotope-reinforced polyunsaturated fatty acids protect yeast cells from oxidative stress.Free radical biology & medicine, 50 1
J. Galano, E. Mas, A. Barden, Trevor Mori, C. Signorini, C. Felice, Aaron Barrett, C. Opere, Edith Pinot, E. Schwedhelm, R. Benndorf, Jérôme Roy, J. Guennec, C. Oger, T. Durand (2013)
Isoprostanes and neuroprostanes: total synthesis, biological activity and biomarkers of oxidative stress in humans.Prostaglandins & other lipid mediators, 107
J. Hollyfield, V. Perez, R. Salomon (2010)
A Hapten Generated from an Oxidation Fragment of Docosahexaenoic Acid Is Sufficient to Initiate Age-Related Macular DegenerationMolecular Neurobiology, 41
Accepted Article published
Shauna Hill, C. Lamberson, Libin Xu, R. To, H. Tsui, V. Shmanai, A. Bekish, Agape Awad, B. Marbois, C. Cantor, N. Porter, C. Clarke, M. Shchepinov (2012)
Small amounts of isotope-reinforced polyunsaturated fatty acids suppress lipid autoxidation.Free radical biology & medicine, 53 4
Tonino Caruso, A. Spinella (2002)
First total synthesis of natural aplyolides C and E, ichthyotoxic macrolides isolated from the skin of the marine mollusc Aplysia depilans ☆Tetrahedron-asymmetry, 13
(2013)
Prostaglandins Other Lipid Mediators
C. Brown, V. Ahuja (1973)
“P-2 nickel” catalyst with ethylenediamine, a novel system for highly stereospecific reduction of alkynes to cis-olefinsJournal of The Chemical Society, Chemical Communications
Gulin Erdogan, D. Grotjahn (2009)
Mild and selective deuteration and isomerization of alkenes by a bifunctional catalyst and deuterium oxide.Journal of the American Chemical Society, 131 30
M. Jakobsen, A. Vik, T. Hansen (2012)
Concise syntheses of three ω-3 polyunsaturated fatty acidsTetrahedron Letters, 53
Jeffrey Cannon, S. Kirsch, L. Overman, H. Sneddon (2010)
Mechanism of the cobalt oxazoline palladacycle (COP)-catalyzed asymmetric synthesis of allylic esters.Journal of the American Chemical Society, 132 43
C. Spickett (2013)
The lipid peroxidation product 4-hydroxy-2-nonenal: Advances in chemistry and analysis☆Redox Biology, 1
U. Jahn, J. Galano, T. Durand (2008)
Beyond prostaglandins--chemistry and biology of cyclic oxygenated metabolites formed by free-radical pathways from polyunsaturated fatty acids.Angewandte Chemie, 47 32
A. Andreyev, H. Tsui, G. Milne, V. Shmanai, A. Bekish, M. Fomich, Minhhan Pham, Yvonne Nong, A. Murphy, C. Clarke, M. Shchepinov (2015)
Isotope-reinforced polyunsaturated fatty acids protect mitochondria from oxidative stress.Free radical biology & medicine, 82
Eric Long, M. Picklo (2010)
Trans-4-hydroxy-2-hexenal, a product of n-3 fatty acid peroxidation: make some room HNE...Free radical biology & medicine, 49 1
Q. Ebrahem, K. Renganathan, J. Sears, A. Vasanji, X. Gu, Liang Lu, R. Salomon, J. Crabb, B. Anand-Apte (2006)
Carboxyethylpyrrole oxidative protein modifications stimulate neovascularization: Implications for age-related macular degenerationProceedings of the National Academy of Sciences, 103
F. Kuijk, L. Holte, E. Dratz (1990)
4-Hydroxyhexenal: a lipid peroxidation product derived from oxidized docosahexaenoic acid.Biochimica et biophysica acta, 1043 1
Rui Wang, A. He, E. Ramu, J. Falck (2015)
Studies towards asymmetric synthesis of 4(S)-11-dihydroxydocosahexaenoic acid (diHDHA) featuring cross-coupling of chiral stannane under mild conditions.Organic & biomolecular chemistry, 13 6
T. Itoh, I. Murota, Kazuyoshi Yoshikai, S. Yamada, Keiko Yamamoto (2006)
Synthesis of docosahexaenoic acid derivatives designed as novel PPARgamma agonists and antidiabetic agents.Bioorganic & medicinal chemistry, 14 1
A. Holmeide, L. Skattebol (2000)
Syntheses of some polyunsaturated trifluoromethyl ketones as potential phospholipase A2 inhibitorsJournal of The Chemical Society-perkin Transactions 1
R. Ireland, Longbin Liu, T. Roper (1997)
Total synthesis of FK-506. Part 1: Construction of the C16–C34 fragment☆Tetrahedron, 53
C. Serhan, N. Petasis (2011)
Resolvins and protectins in inflammation resolution.Chemical reviews, 111 10
(2008)
Lipid Res. 2016
Céline Crauste, C. Vigor, P. Brabet, M. Picq, M. Lagarde, C. Hamel, T. Durand, J. Vercauteren (2014)
Synthesis and Evaluation of Polyunsaturated Fatty Acid–Phenol Conjugates as Anti‐Carbonyl‐Stress LipophenolsEuropean Journal of Organic Chemistry, 2014
T. Georgiou, A. Neokleous, D. Nicolaou, B. Sears (2014)
Pilot study for treating dry age-related macular degeneration (AMD) with high-dose omega-3 fatty acidsPharmaNutrition, 2
K. Mori, T. Ebata (1986)
Syntheses of optically active pheromones with an epoxy ring, (+)-disparlure and both the enantiomers of (3z,6z)-cis-9,10-epoxy-3,6-heneicosadieneTetrahedron, 42
J. Sangiovanni, E. Chew (2005)
The role of omega-3 long-chain polyunsaturated fatty acids in health and disease of the retinaProgress in Retinal and Eye Research, 24
17:83;i socratic flow; UV detection:2 17 nm) to give pure deuterated DHA
Feng Li, L. Marchette, R. Brush, M. Elliott, K. Davis, Ashley Anderson, R. Anderson (2010)
High levels of retinal docosahexaenoic acid do not protect photoreceptor degeneration in VPP transgenic miceMolecular Vision, 16
G. Dayaker, T. Durand, L. Balas (2014)
A versatile and stereocontrolled total synthesis of dihydroxylated docosatrienes containing a conjugated E,E,Z-triene.Chemistry, 20 10
CDCl 3 ): d = 5.43-5.30 (m, 12 H; CH), 2.86-2.80 (m, 6H;C H 2(bis-allylic)
CDCl 3 ): d = 5.40-5.32 (m, 12 H; CH), 4.12 (q, 3 J(H,H) = 7Hz, 2H;C H 2(ester) ), 2.86-2.80 (m, 6H;C H 2(bis-allylic) ), 2.39-2.34 (m, 4H;C H 2 ÀCH 2 ÀCO
D. Rice, J. Calandria, W. Gordon, Bokkyoo Jun, Yongdong Zhou, C. Gelfman, Songhua Li, M. Jin, Eric Knott, Bo Chang, Alex Abuin, T. Issa, David Potter, K. Platt, N. Bazan (2015)
Adiponectin receptor 1 conserves docosahexaenoic acid and promotes photoreceptor cell survivalNature Communications, 6
A. Ishikado, K. Morino, Y. Nishio, Fumiyuki Nakagawa, Atsushi Mukose, Yoko Sono, Nagisa Yoshioka, Keiko Kondo, Osamu Sekine, Takeshi Yoshizaki, S. Ugi, T. Uzu, Hiromichi Kawai, T. Makino, T. Okamura, Masayuki Yamamoto, A. Kashiwagi, H. Maegawa (2013)
4-Hydroxy Hexenal Derived from Docosahexaenoic Acid Protects Endothelial Cells via Nrf2 ActivationPLoS ONE, 8
N. Bazan, V. Marcheselli, Kasie Cole-Edwards (2005)
Brain response to injury and neurodegeneration: endogenous neuroprotective signaling.Annals of the New York Academy of Sciences, 1053
Jérôme Roy, C. Oger, J. Thireau, J. Roussel, Olivia Mercier-Touzet, Delinger Faure, Edith Pinot, C. Farah, D. Taber, J. Cristol, J. Lee, A. Lacampagne, J. Galano, T. Durand, J. Guennec (2015)
Nonenzymatic lipid mediators, neuroprostanes, exert the antiarrhythmic properties of docosahexaenoic acid.Free radical biology & medicine, 86
C. Lamberson, Libin Xu, H. Muchalski, J. Montenegro-Burke, V. Shmanai, A. Bekish, J. McLean, C. Clarke, M. Shchepinov, N. Porter (2014)
Unusual kinetic isotope effects of deuterium reinforced polyunsaturated fatty acids in tocopherol-mediated free radical chain oxidations.Journal of the American Chemical Society, 136 3
Mattia Nunzio, V. Valli, A. Bordoni (2016)
PUFA and oxidative stress. Differential modulation of the cell response by DHAInternational Journal of Food Sciences and Nutrition, 67
A. Simopoulos (2002)
Omega-3 Fatty Acids in Inflammation and Autoimmune DiseasesJournal of the American College of Nutrition, 21
The deuteration of polyunsaturated fatty acids (PUFAs) at their bis‐allylic positions is known to limit harmful lipid peroxidation, which leads to the damage of cell membranes. Therefore, to impede toxic lipid peroxidation in retina tissue, we have designed and synthesized two deuterated analogues of docosahexaenoic acid (DHA; C22:6, n‐3), which is the main lipid constituent of retina membranes. To avoid its oxidative degradation into toxic carboxyethylpyrrole (CEP) adducts, whilst preserving enzymatic metabolization into a healthy neuroprotectine derivative (NPD1), deuterium was incorporated at specific 6‐ and 6,9‐bis‐allylic positions. A convergent synthetic strategy, based on a Wittig olefination, was developed to obtain both deuterated DHA species. Common aldehyde intermediates were synthesized from another PUFA, eicosapentaenoic acid (EPA; C20:5, n‐3). Deuterium atoms were introduced through either the reduction of an ester with a deuterated reagent or a nucleophilic reaction with deuterated paraformaldehyde.
Asian Journal of Organic Chemistry – Wiley
Published: Mar 1, 2017
Keywords: ; ; ; ;
Read and print from thousands of top scholarly journals.
Already have an account? Log in
Bookmark this article. You can see your Bookmarks on your DeepDyve Library.
To save an article, log in first, or sign up for a DeepDyve account if you don’t already have one.
Copy and paste the desired citation format or use the link below to download a file formatted for EndNote
Access the full text.
Sign up today, get DeepDyve free for 14 days.
All DeepDyve websites use cookies to improve your online experience. They were placed on your computer when you launched this website. You can change your cookie settings through your browser.