- 12-LIPOXYGENASE ACTIVITY IN THE RED MARINE ALGA GRACILARIOPSIS LEMANEIFORMIS
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The temperate red alga Gracilariopsis lemaneiformis is a rich source of polyunsaturated fatty acids that are regio-specifically oxidized at C-12.In this in vitro study, we demonstrate the existence of a highly active lipoxygenase-type activity in Gracilariopsis.GC-MS of the methyl ester, trimethylsilyl ether derivatives of the crude reaction mixture identified the production of 12-hydroxyicosatetraenoic acid, a 12-lipoxygenase product previously isolated from this alga.This is the first report of 12-lipoxygenase-type activity from the plant kingdom.
- Moghaddam, Mehran Fallah,Gerwick, William H.
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- Crystal structure of a lipoxygenase in complex with substrate: The arachidonic acid-binding site of 8R-lipoxygenase
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Lipoxygenases (LOX) play critical roles in mammalian biology in the generation of potent lipid mediators of the inflammatory response; consequently, they are targets for the development of isoform-specific inhibitors. The regio- and stereo-specificity of the oxygenation of polyunsaturated fatty acids by the enzymes is understood in terms of the chemistry, but structural observation of the enzyme-substrate interactions is lacking. Although several LOX crystal structures are available, heretofore the rapid oxygenation of bound substrate has precluded capture of the enzyme-substrate complex, leaving a gap between chemical and structural insights. In this report, we describe the 2.0 ? resolution structure of 8R-LOX in complex with arachidonic acid obtained under anaerobic conditions. Subtle rearrangements, primarily in the side chains of three amino acids, allow binding of arachidonic acid in a catalytically competent conformation. Accompanying experimental work supports a model in which both substrate tethering and cavity depth contribute to positioning the appropriate carbon at the catalytic machinery.
- Neau, David B.,Bender, Gunes,Boeglin, William E.,Bartlett, Sue G.,Brash, Alan R.,Newcomer, Marcia E.
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p. 31905 - 31913
(2015/02/19)
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- Physcomitrella patens has lipoxygenases for both eicosanoid and octadecanoid pathways
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Mosses have substantial amounts of long chain C20 polyunsaturated fatty acids, such as arachidonic and eicosapentaenoic acid, in addition to the shorter chain C18 α-linolenic and linoleic acids, which are typical substrates of lipoxygenases in flowering p
- Anterola, Aldwin,G?bel, Cornelia,Hornung, Ellen,Sellhorn, George,Feussner, Ivo,Grimes, Howard
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experimental part
p. 40 - 52
(2009/07/11)
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- Total synthesis of 12(R)-HETE, 12(S)-HETE, 2H2-12(R)-HETE and LTB4 from racemic glycidol via hydrolytic kinetic resolution
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The total synthesis of 12(R)-HETE, 12(S)-HETE (Samuelsson's HETE), [14,15-2H2]-12(R)-HETE and Leukotriene B4 from racemic glycidol is described. The key steps are the hydrolytic kinetic resolution of racemic TES-glycidol with salen-Co catalyst and the selective oxidation of primary silyl ethers, in the presence of secondary ones, under Swern conditions to give a short entry to both enantiomers of 12-HETE and LTB4.
- Rodríguez,Nomen,Spur,Godfroid,Lee
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- A short catalytic enantioselective synthesis of the proinflammatory eicosanoid 12(R)-hydroxy-5(Z),8(Z),10(E),14(Z)-eicosatetraenoic acid (12(R)-HETE)
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(equation presented) A new and effective pathway is described for the synthesis of 12(R)-HETE and the 12(S)-enantiomer from the common intermediates 4 and 8.
- Han, Xiaojun,Corey
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p. 2543 - 2544
(2007/10/03)
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- A CONCISE SYNTHESIS OF (R)-HYDROXY-E,Z-DIENE FATTY ACIDS: PREPARATION OF 12(R)-HETE, TETRANOR-12(R)-HETE, AND 13(R)-HODE
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Chiral E-enals derived from functionalized 2-deoxy-D-ribofuranoses by ylide-induced β-elimination were exploited for the synthesis of fatty acid metabolites containing (R)-hydroxy-E,Z-diene subunit.
- Lumin, Sun,Falck, J. R.,Schwartzman, Michal L.
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p. 2315 - 2318
(2007/10/02)
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- TOTAL ENANTIOSPECIFIC SYNTHESIS OF 12(R)-HETE
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A total synthesis of 12(R)-hydroxy-5,8,14-cis-10-trans-eicosatetraenoic acid was accomplished via a short, efficient, enantiospecific route.
- Taffer, Ira M.,Zipkin, Robert E.
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p. 6543 - 6544
(2007/10/02)
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- ENANTIOSPECIFIC TOTAL SYNTHESIS OF 8- and 12-HYDROXYEICOSATETRAENOIC ACID
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The R- and S-isomers of 8- and 12-hidroxyeicosatetraenoic acid (8- and 12-HETE) were synthesized from dimethyl malate derived precursors.
- Yadagiri, Pendri,Lumin, Sun,Mosset, Paul,Capdevila, Jorge,Falck, J. R.
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p. 6039 - 6040
(2007/10/02)
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