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(9S,10E,12Z)-9-hydroperoxyoctadeca-10,12-dienoate = (8E)-9-[(1E,3Z)-nona-1,3-dien-1-yloxy]non-8-enoate + H2O
(9S,10E,12Z)-9-hydroperoxyoctadeca-10,12-dienoate = (8E)-9-[(1E,3Z)-nona-1,3-dien-1-yloxy]non-8-enoate + H2O
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(9S,10E,12Z)-9-hydroperoxyoctadeca-10,12-dienoate = (8E)-9-[(1E,3Z)-nona-1,3-dien-1-yloxy]non-8-enoate + H2O
intervention of an epoxycarbonium ion intermediate. A mechanism is proposed
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(9S,10E,12Z)-9-hydroperoxyoctadeca-10,12-dienoate = (8E)-9-[(1E,3Z)-nona-1,3-dien-1-yloxy]non-8-enoate + H2O
selective removal of the pro-R hydrogen at C-8 in the biosynthesis of colneleic acid
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(9S,10E,12Z)-9-hydroperoxyoctadeca-10,12-dienoate = (8E)-9-[(1E,3Z)-nona-1,3-dien-1-yloxy]non-8-enoate + H2O
the oxygen inserted enzymically between carbons 9- and 10- of the C-18 chain in forming colneleic acid originates from 18O2 gas via the hydroperoxide group of linoleic acid. A mechanism is proposed
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(9S,10E,12Z)-9-hydroperoxyoctadeca-10,12-dienoate = (8E)-9-[(1E,3Z)-nona-1,3-dien-1-yloxy]non-8-enoate + H2O
selective removal of the pro-R hydrogen at C-8 in the biosynthesis of colneleic acid
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(9S)-hydroperoxylinoleic acid + H2O
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potato divinyl ether synthase stereospecifically utilizes (9S)-hydroperoxylinoleic acid
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?
(9S)-hydroperoxylinoleic acid + H2O
colneleic acid
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?
(9S,10E,12Z)-9-hydroperoxy-10,12-octadecadienoate
(8E)-9-[(1E,3Z)-nona-1,3-dien-1-yloxy]non-8-enoic acid + H2O
(9S,10E,12Z)-9-hydroperoxy-10,12-octadecadienoic acid + H2O
colneleic acid
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i.e. 9-[1'E,3'Z-nonadienyloxy]-8E-nonenoic acid
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?
(9S,10E,12Z)-9-hydroperoxyoctadeca-10,12-dienoate + H2O
9-[1'(E),3'(Z)-nonadienyloxy]-8(E)-nonenoic acid
(9S,10E,12Z,15Z)-9-hydroperoxy-10,12,15-octadecatrienoate
(8E)-9-[(1E,3Z,6Z)-nona-1,3,6-trien-1-yloxy]non-8-enoic acid + H2O
(9S,10E,12Z,15Z)-9-hydroperoxy-10,12,15-octadecatrienoic acid + H2O
9-[1'(E),3'(Z),6'(Z)-nonatrienyloxy]-8(E)-nonenoic acid
(9S,10E,12Z,15Z)-9-hydroperoxy-10,12,15-octadecatrienoic acid + H2O
colnelenic acid
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i.e 9-[1'E,3'Z,6'Z-nonatrienyloxy]-8E-nonenoic acid
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?
additional information
?
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(9S,10E,12Z)-9-hydroperoxy-10,12-octadecadienoate
(8E)-9-[(1E,3Z)-nona-1,3-dien-1-yloxy]non-8-enoic acid + H2O
the corresponding 13-hydroperoxide is a poor substrate
i.e. colneleate, characterization of the product
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?
(9S,10E,12Z)-9-hydroperoxy-10,12-octadecadienoate
(8E)-9-[(1E,3Z)-nona-1,3-dien-1-yloxy]non-8-enoic acid + H2O
poorly active against the the corresponding 13-hydroperoxide
i.e. colneleate, characterization of the product
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?
(9S,10E,12Z)-9-hydroperoxy-10,12-octadecadienoate
(8E)-9-[(1E,3Z)-nona-1,3-dien-1-yloxy]non-8-enoic acid + H2O
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i.e. colneleate
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?
(9S,10E,12Z)-9-hydroperoxy-10,12-octadecadienoate
(8E)-9-[(1E,3Z)-nona-1,3-dien-1-yloxy]non-8-enoic acid + H2O
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i.e. colneleate, the fatty acid derivative colneleate functions as a plant antimicrobial compound
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?
(9S,10E,12Z)-9-hydroperoxy-10,12-octadecadienoate
(8E)-9-[(1E,3Z)-nona-1,3-dien-1-yloxy]non-8-enoic acid + H2O
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intervention of an epoxycarbonium ion intermediate. A mechanism is proposed
i.e. colneleate
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?
(9S,10E,12Z)-9-hydroperoxy-10,12-octadecadienoate
(8E)-9-[(1E,3Z)-nona-1,3-dien-1-yloxy]non-8-enoic acid + H2O
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selective removal of the pro-R hydrogen at C-8 in the biosynthesis of colneleic acid
i.e. colneleate
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?
(9S,10E,12Z)-9-hydroperoxy-10,12-octadecadienoate
(8E)-9-[(1E,3Z)-nona-1,3-dien-1-yloxy]non-8-enoic acid + H2O
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selective removal of the pro-R hydrogen at C-8 in the biosynthesis of colneleic acid. Generation of colneleic acid from the (8R)-deuterated (9S)-hydroperoxide is accompanied by loss of most of the deuterium label (retention, 8%)
i.e. colneleate
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?
(9S,10E,12Z)-9-hydroperoxy-10,12-octadecadienoate
(8E)-9-[(1E,3Z)-nona-1,3-dien-1-yloxy]non-8-enoic acid + H2O
the corresponding 13-hydroperoxide is not accepted as substrate
i.e. colneleate, characterization of the product
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?
(9S,10E,12Z)-9-hydroperoxy-10,12-octadecadienoate
(8E)-9-[(1E,3Z)-nona-1,3-dien-1-yloxy]non-8-enoic acid + H2O
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i.e. colneleate
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?
(9S,10E,12Z)-9-hydroperoxy-10,12-octadecadienoate
(8E)-9-[(1E,3Z)-nona-1,3-dien-1-yloxy]non-8-enoic acid + H2O
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selective removal of the pro-R hydrogen at C-8 in the biosynthesis of colneleic acid
i.e. colneleate
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?
(9S,10E,12Z)-9-hydroperoxyoctadeca-10,12-dienoate + H2O
9-[1'(E),3'(Z)-nonadienyloxy]-8(E)-nonenoic acid
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i.e. colneleic acid
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?
(9S,10E,12Z)-9-hydroperoxyoctadeca-10,12-dienoate + H2O
9-[1'(E),3'(Z)-nonadienyloxy]-8(E)-nonenoic acid
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i.e. colneleic acid
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?
(9S,10E,12Z,15Z)-9-hydroperoxy-10,12,15-octadecatrienoate
(8E)-9-[(1E,3Z,6Z)-nona-1,3,6-trien-1-yloxy]non-8-enoic acid + H2O
the corresponding 13-hydroperoxide is a poor substrate
i.e. colnelenate
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?
(9S,10E,12Z,15Z)-9-hydroperoxy-10,12,15-octadecatrienoate
(8E)-9-[(1E,3Z,6Z)-nona-1,3,6-trien-1-yloxy]non-8-enoic acid + H2O
poorly active against the the corresponding 13-hydroperoxide
i.e. colnelenate
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?
(9S,10E,12Z,15Z)-9-hydroperoxy-10,12,15-octadecatrienoate
(8E)-9-[(1E,3Z,6Z)-nona-1,3,6-trien-1-yloxy]non-8-enoic acid + H2O
the corresponding 13-hydroperoxide is not accepted as substrate
i.e. colnelenic acid
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?
(9S,10E,12Z,15Z)-9-hydroperoxy-10,12,15-octadecatrienoic acid + H2O
9-[1'(E),3'(Z),6'(Z)-nonatrienyloxy]-8(E)-nonenoic acid
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i.e. colnelenic acid
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?
(9S,10E,12Z,15Z)-9-hydroperoxy-10,12,15-octadecatrienoic acid + H2O
9-[1'(E),3'(Z),6'(Z)-nonatrienyloxy]-8(E)-nonenoic acid
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i.e. colnelenic acid
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additional information
?
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the enzyme utilizes linoleic and alpha-linolenic acid 9-hydroperoxides as substrates, but is inactive towards 13-hydroperoxides
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additional information
?
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irrespective of which hydroperoxide regioisomer serves as the substrate, divinyl ether synthases abstracting the pro-R hydrogen generate divinyl ethers having an (E)-vinyl ether double bond, whereas enzymes abstracting the pro-S hydrogen produce divinyl ethers having a (Z)-vinyl ether double bond
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additional information
?
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13-hydroperoxides are only poor substrates
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?
additional information
?
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the enzyme utilizes linoleic and alpha-linolenic acid 9-hydroperoxides as substrates, but is inactive towards 13-hydroperoxides
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?
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Hamberg, M.
Hidden stereospecificity in the biosynthesis of divinyl ether fatty acids
FEBS J.
272
736-743
2005
Solanum tuberosum
brenda
Stumpe, M.; Kandzia, R.; Gobel, C.; Rosahl, S.; Feussner, I.
A pathogen-inducible divinyl ether synthase (CYP74D) from elicitor-treated potato suspension cells
FEBS Lett.
507
371-376
2001
Solanum tuberosum (Q9AVQ1), Solanum tuberosum
brenda
Itoh, A.; Howe, G.A.
Molecular cloning of a divinyl ether synthase. Identification as a CYP74 cytochrome P-450
J. Biol. Chem.
276
3620-3627
2001
Solanum lycopersicum (Q9FPM6), Solanum lycopersicum
brenda
Gbel, C.; Feussner, I.; Schmidt, A.; Scheel, D.; Sanchez-Serrano, J.; Hamberg, M.; Rosahl, S.
Oxylipin profiling reveals the preferential stimulation of the 9-lipoxygenase pathway in elicitor-treated potato cells
J. Biol. Chem.
276
6267-6273
2001
Solanum tuberosum
brenda
Crombie, L.; Morgan, D.O.; Smith, E.H.
The enzymic formation of colneleic acid, a divinyl ether fatty acid: experiments with [(9S)-18O2]hydroperoxyoctadeca-(10E),(12Z)-dienoic acid
J. Chem. Soc. Chem. Commun.
1987
502-503
1987
Solanum tuberosum
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brenda
Crombie, L.; Morgan, D.O.; Smith, E.H.
An isotopic study (2H and 18O) of the enzymic conversion of linoleic acid into colneleic acid with carbon chain fracture: the origin of shorter chain aldehydes
J. Chem. Soc. Perkin Trans. I
1991
567-575
1991
Solanum tuberosum
-
brenda
Fahlstadius, P.; Hamberg, M.
Stereospecific removal of the pro-R hydrogen at C-8 of (9S)-hydroperoxyoctadecadienoic acid in the biosynthesis of colneleic acid
J. Chem. Soc. Perkin Trans.
1990
2027-2030
1990
Solanum tuberosum, Solanum tuberosum Bintje
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brenda
Fammartino, A.; Cardinale, F.; Gbel, C.; Mene-Saffrane, L.; Fournier, J.; Feussner, I.; Esquerre-Tugaye, M.T.
Characterization of a divinyl ether biosynthetic pathway specifically associated with pathogenesis in tobacco
Plant Physiol.
143
378-388
2007
Nicotiana tabacum (Q8W2N5), Nicotiana tabacum
brenda
Stumpe, M.; Feussner, I.
Formation of oxylipins by CYP74 enzymes
Phytochem. Rev.
5
347-357
2006
Solanum tuberosum (Q9AVQ1)
-
brenda
Eschen-Lippold, L.; Rothe, G.; Stumpe, M.; Goebel, C.; Feussner, I.; Rosahl, S.
Reduction of divinyl ether-containing polyunsaturated fatty acids in transgenic potato plants
Phytochemistry
68
797-801
2007
Solanum tuberosum
brenda
Fammartino, A.; Verdaguer, B.; Fournier, J.; Tamietti, G.; Carbonne, F.; Esquerre-Tugaye, M.T.; Cardinale, F.
Coordinated transcriptional regulation of the divinyl ether biosynthetic genes in tobacco by signal molecules related to defense
Plant Physiol. Biochem.
48
225-231
2010
Nicotiana tabacum
brenda
Grechkin, A.N.
Hydroperoxide lyase and divinyl ether synthase
Prostaglandins Other Lipid Mediat.
68-69
457-470
2002
Solanum lycopersicum, Solanum tuberosum
brenda
4.2.1.121 colneleate synthase
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