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(9S,10E,12Z,14E,16S)-9,16-bis(hydroperoxy)octadecatrienoate |
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CHEBI:133991 |
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(9S,10E,12Z,14E,16S)-9,16-bis(hydroperoxy)octadecatrienoate |
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A hydroperoxyoctadecatrienoate that is the conjugate base of (9S,10E,12Z,14E,16S)-9,16-bis(hydroperoxy)octadecatrienoic acid, obtained by deprotonation of the carboxy group. Major microspecies at pH 7.3. |
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This entity has been manually annotated by the ChEBI Team.
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Anne Morgat
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No supplier information found for this compound. |
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Molfile
XML
SDF
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InChI=1S/C18H30O6/c1- 2- 16(23- 21) 12- 8- 6- 7- 10- 14- 17(24- 22) 13- 9- 4- 3- 5- 11- 15- 18(19) 20/h6- 8,10,12,14,16- 17,21- 22H,2- 5,9,11,13,15H2,1H3,(H,19,20) /p- 1/b7- 6- ,12- 8+,14- 10+/t16- ,17- /m0/s1 |
MFVHQYMRUDEPIO-NYOLHIHQSA-M |
C(CCCCCCC[C@@H](/C=C/C=C\C=C\[C@H](CC)OO)OO)([O-])=O |
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Outgoing
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(9S,10E,12Z,14E,16S)-9,16-bis(hydroperoxy)octadecatrienoate
(CHEBI:133991)
is a
hydroperoxyoctadecatrienoate
(CHEBI:133558)
(9S,10E,12Z,14E,16S)-9,16-bis(hydroperoxy)octadecatrienoate
(CHEBI:133991)
is conjugate base of
(9S,10E,12Z,14E,16S)-9,16-bis(hydroperoxy)octadecatrienoic acid
(CHEBI:133990)
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Incoming
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(9S,10E,12Z,14E,16S)-9,16-bis(hydroperoxy)octadecatrienoic acid
(CHEBI:133990)
is conjugate acid of
(9S,10E,12Z,14E,16S)-9,16-bis(hydroperoxy)octadecatrienoate
(CHEBI:133991)
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(9S,10E,12Z,14E,16S)- 9,16- bis(hydroperoxy)octadeca- 10,12,14- trienoate
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(10E,12Z,14E)- (9S,16S)- 9,16- dihydroperoxyoctadeca- 10,12,14- trienoate
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SUBMITTER
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(9S,16S)-dihydroperoxy-(10E,12Z,14E)-octadecatrienoate
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UniProt
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9S,16S-DiHPOTrE(1−)
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SUBMITTER
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Wennman A, Jernerén F, Magnuson A, Oliw EH (2015) Expression and characterization of manganese lipoxygenase of the rice blast fungus reveals prominent sequential lipoxygenation of α-linolenic acid. Archives of biochemistry and biophysics 583, 87-95 (Source: SUBMITTER) [PubMed:26264916] [show Abstract] Magnaporthe oryzae causes rice blast disease and has become a model organism of fungal infections. M. oryzae can oxygenate fatty acids by 7,8-linoleate diol synthase, 10R-dioxygenase-epoxy alcohol synthase, and by a putative manganese lipoxygenase (Mo-MnLOX). The latter two are transcribed during infection. The open reading frame of Mo-MnLOX was deduced from genome and cDNA analysis. Recombinant Mo-MnLOX was expressed in Pichia pastoris and purified to homogeneity. The enzyme contained protein-bound Mn and oxidized 18:2n-6 and 18:3n-3 to 9S-, 11-, and 13R-hydroperoxy metabolites by suprafacial hydrogen abstraction and oxygenation. The 11-hydroperoxides were subject to β-fragmentation with formation of 9S- and 13R-hydroperoxy fatty acids. Oxygen consumption indicated apparent kcat values of 2.8 s(-1) (18:2n-6) and 3.9 s(-1) (18:3n-3), and UV analysis yielded apparent Km values of 8 and 12 μM, respectively, for biosynthesis of cis-trans conjugated metabolites. 9S-Hydroperoxy-10E,12Z,15Z-octadecatrienoic acid was rapidly further oxidized to a triene, 9S,16S-dihydroperoxy-10E,12Z,14E-octadecatrienoic acid. In conclusion, we have expressed, purified and characterized a new MnLOX from M. oryzae. The pathogen likely secretes Mo-MnLOX and phospholipases to generate oxylipins and to oxidize lipid membranes of rice cells and the cuticle. |
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