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(9Z,12Z)-octadeca-9,12-dienoic acid
(9Z,11E)-octadeca-9,11-dienoic acid
11-cis,14-cis-eicosadienoic acid
?
-
-
-
-
?
2,5-Octadecadienoic acid
3,5-Octadecadienoic acid
-
-
-
?
6-cis,9-cis,12-cis,15-cis-octadecatetraenoic acid
?
-
i.e. stearidonic acid
-
-
?
6-cis,9-cis,12-cis-octadecatrienoic acid
?
-
i.e. alpha-linolenic acid
-
-
?
9-cis,11-trans-linoleic acid
9-trans,11-trans-linoleic acid
9-cis,12-cis,15-cis-octadecatrienoic acid
?
-
i.e. gamma-linolenic acid
-
-
?
9-cis,12-cis-linoleic acid
9-cis,11-trans-linoleic acid
9-cis,12-cis-linoleic acid
9-cis,11-trans-linoleic acid + 9-trans,11-trans-linoleic acid
9-cis,12-cis-linoleic acid
9-trans,11-trans-linoleic acid
9-cis,12-cis-Octadecadienoate
9-cis,11-trans-Octadecadienoate
9-cis,12-cis-Octadecadienoate
?
-
initial reaction of the biohydrogenation pathway
-
-
?
cis-9,cis-12,cis-15-octadecatrienoic acid
cis-9,trans-11,cis-15-octadecatrienoic acid
-
-
-
?
linoleic acid
(9E,11E)-octadeca-9,11-dienoic acid
-
-
-
?
linoleic acid
(9Z,11E)-octadeca-9,11-dienoic acid
linoleic acid
conjugated linoleic acid
additional information
?
-
(9Z,12Z)-octadeca-9,12-dienoic acid
(9Z,11E)-octadeca-9,11-dienoic acid
-
-
i.e. rumenic acid
-
?
(9Z,12Z)-octadeca-9,12-dienoic acid
(9Z,11E)-octadeca-9,11-dienoic acid
-
-
i.e. rumenic acid
-
?
(9Z,12Z)-octadeca-9,12-dienoic acid
(9Z,11E)-octadeca-9,11-dienoic acid
-
-
i.e. rumenic acid
-
?
(9Z,12Z)-octadeca-9,12-dienoic acid
(9Z,11E)-octadeca-9,11-dienoic acid
-
-
i.e. rumenic acid
-
?
(9Z,12Z)-octadeca-9,12-dienoic acid
(9Z,11E)-octadeca-9,11-dienoic acid
-
-
i.e. rumenic acid
-
?
9-cis,11-trans-linoleic acid
9-trans,11-trans-linoleic acid
-
formation only under aerobic conditions
-
-
?
9-cis,11-trans-linoleic acid
9-trans,11-trans-linoleic acid
-
-
-
?
9-cis,11-trans-linoleic acid
9-trans,11-trans-linoleic acid
-
-
-
?
9-cis,12-cis-linoleic acid
9-cis,11-trans-linoleic acid
-
-
-
-
?
9-cis,12-cis-linoleic acid
9-cis,11-trans-linoleic acid
-
-
-
-
?
9-cis,12-cis-linoleic acid
9-cis,11-trans-linoleic acid
-
higher activity under aerobic than under anaerobic conditions
conjugated linoleic acid isomer
-
?
9-cis,12-cis-linoleic acid
9-cis,11-trans-linoleic acid
-
-
-
?
9-cis,12-cis-linoleic acid
9-cis,11-trans-linoleic acid
-
-
-
?
9-cis,12-cis-linoleic acid
9-cis,11-trans-linoleic acid
-
-
-
-
?
9-cis,12-cis-linoleic acid
9-cis,11-trans-linoleic acid
-
-
-
-
?
9-cis,12-cis-linoleic acid
9-cis,11-trans-linoleic acid
-
-
-
-
?
9-cis,12-cis-linoleic acid
9-cis,11-trans-linoleic acid
-
-
-
-
?
9-cis,12-cis-linoleic acid
9-cis,11-trans-linoleic acid
-
-
-
-
?
9-cis,12-cis-linoleic acid
9-cis,11-trans-linoleic acid
-
-
-
?
9-cis,12-cis-linoleic acid
9-cis,11-trans-linoleic acid
-
-
-
?
9-cis,12-cis-linoleic acid
9-cis,11-trans-linoleic acid
-
-
-
?
9-cis,12-cis-linoleic acid
9-cis,11-trans-linoleic acid
-
-
-
?
9-cis,12-cis-linoleic acid
9-cis,11-trans-linoleic acid
-
-
-
-
?
9-cis,12-cis-linoleic acid
9-cis,11-trans-linoleic acid
-
the enzyme shows high specificity for the production of the cis-9, trans-11 conjugated linoleic acid isomer
-
-
?
9-cis,12-cis-linoleic acid
9-cis,11-trans-linoleic acid
-
the enzyme shows high specificity for the production of the cis-9, trans-11 conjugated linoleic acid isomer
-
-
?
9-cis,12-cis-linoleic acid
9-cis,11-trans-linoleic acid
-
-
-
-
?
9-cis,12-cis-linoleic acid
9-cis,11-trans-linoleic acid
-
-
-
-
?
9-cis,12-cis-linoleic acid
9-cis,11-trans-linoleic acid
-
-
-
-
?
9-cis,12-cis-linoleic acid
9-cis,11-trans-linoleic acid + 9-trans,11-trans-linoleic acid
-
-
-
-
?
9-cis,12-cis-linoleic acid
9-cis,11-trans-linoleic acid + 9-trans,11-trans-linoleic acid
-
-
-
-
?
9-cis,12-cis-linoleic acid
9-trans,11-trans-linoleic acid
-
-
-
-
?
9-cis,12-cis-linoleic acid
9-trans,11-trans-linoleic acid
-
-
-
-
?
9-cis,12-cis-linoleic acid
9-trans,11-trans-linoleic acid
-
-
-
-
?
9-cis,12-cis-Octadecadienoate
9-cis,11-trans-Octadecadienoate
-
-
-
-
?
9-cis,12-cis-Octadecadienoate
9-cis,11-trans-Octadecadienoate
-
-
-
?
9-cis,12-cis-Octadecadienoate
9-cis,11-trans-Octadecadienoate
-
r
-
?
9-cis,12-cis-Octadecadienoate
9-cis,11-trans-Octadecadienoate
-
9,12-octadienoic acid
-
?
linoleic acid
(9Z,11E)-octadeca-9,11-dienoic acid
-
-
-
-
?
linoleic acid
(9Z,11E)-octadeca-9,11-dienoic acid
-
-
-
?
linoleic acid
conjugated linoleic acid
-
-
-
-
?
linoleic acid
conjugated linoleic acid
-
-
-
-
?
additional information
?
-
-
substrate specificity, overview, the enzyme is specific for substrates containing cis double bonds at the c9 and c12 positions of C18 polyunsaturated fatty acids, a free carboxyl group is absolutely necessary for isomerization
-
-
?
additional information
?
-
enzyme shows oleate hydratase activity, reaction of EC 4.2.1.53, but does not display linoleate isomerase activity
-
-
?
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9-cis,11-trans-linoleic acid
9-trans,11-trans-linoleic acid
-
formation only under aerobic conditions
-
-
?
9-cis,12-cis-linoleic acid
9-cis,11-trans-linoleic acid
9-cis,12-cis-linoleic acid
9-trans,11-trans-linoleic acid
9-cis,12-cis-Octadecadienoate
9-cis,11-trans-Octadecadienoate
-
-
-
-
?
9-cis,12-cis-Octadecadienoate
?
-
initial reaction of the biohydrogenation pathway
-
-
?
9-cis,12-cis-linoleic acid
9-cis,11-trans-linoleic acid
-
-
-
-
?
9-cis,12-cis-linoleic acid
9-cis,11-trans-linoleic acid
-
-
-
-
?
9-cis,12-cis-linoleic acid
9-cis,11-trans-linoleic acid
-
higher activity under aerobic than under anaerobic conditions
-
-
?
9-cis,12-cis-linoleic acid
9-cis,11-trans-linoleic acid
-
-
-
-
?
9-cis,12-cis-linoleic acid
9-cis,11-trans-linoleic acid
-
-
-
-
?
9-cis,12-cis-linoleic acid
9-cis,11-trans-linoleic acid
-
-
-
-
?
9-cis,12-cis-linoleic acid
9-cis,11-trans-linoleic acid
-
-
-
-
?
9-cis,12-cis-linoleic acid
9-cis,11-trans-linoleic acid
-
-
-
-
?
9-cis,12-cis-linoleic acid
9-cis,11-trans-linoleic acid
-
-
-
-
?
9-cis,12-cis-linoleic acid
9-trans,11-trans-linoleic acid
-
-
-
-
?
9-cis,12-cis-linoleic acid
9-trans,11-trans-linoleic acid
-
-
-
-
?
9-cis,12-cis-linoleic acid
9-trans,11-trans-linoleic acid
-
-
-
-
?
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1,10-phenanthroline
-
reversible, noncompetitive
10,13-Octadecadienoic acid
-
inhibits isomerization of 9,12-octadienoic acid
11,14-Octadecadienoic acid
-
inhibits isomerization of 9,12-octadienoic acid
12,15-Octadecadienoic acid
-
inhibits isomerization of 9,12-octadienoic acid
4,7-Octadecadienoic acid
-
inhibits isomerization of 2,5-octadecadienoic acid and 9,12-octadecadienic acid
5,8-Octadecadienoic acid
-
inhibits isomerization of 2,5-octadecadienoic acid and 9,12-octadecadienic acid
7,10-Octadecadienoic acid
-
inhibits isomerization of 9,12-octadienoic acid
8,11-Octadecadienoic acid
-
inhibits isomerization of 9,12-octadienoic acid
9-cis,12-cis-linoleic acid methyl ester
-
i.e. methyl linoleate, 31% inhibition at 0.02 mM
9-cis,12-cis-octadecadien-1-ol
-
i.e. linoleyl alcohol, 19% inhibition at 0.02 mM
cis,cis,3,6-Octadecadienoic acid
-
inhibits isomerization of 2,5-octadecadienoic acid and 9,12-octadecadienic acid
cis-11,cis-14-Eicosadienic acid
-
inhibits isomerization of 9-cis,12-cis-octadecadienoate
cis-6,cis-9-Octadecadienic acid
-
inhibits isomerization of 9-cis,12-cis-octadecadienoate
cis-8,cis11-Heptadecadienic acid
-
-
cis-9,trans-12-Octadecadienoic acid
-
inhibits isomerization of 9-cis,12-cis-octadecadienoate
cis-9-Octadecen-12-ynoic acid
-
inhibits isomerization of 9-cis,12-cis-octadecadienoate
EGTA
-
93% residual activity at 3 mM
gamma-linolenic acid
-
substrate inhibition at concentrations above 0.015 mM
Linoleamide
-
inhibits isomerization of 9-cis,12-cis-octadecadienoate
linolelaidic acid
-
81% inhibition at 0.02 mM
linolenic acid
-
substrate inhibition at concentrations above 0.04 mM
Linoleyl alcohol
-
inhibits isomerization of 9-cis,12-cis-octadecadienoate
linoleyl amine
-
inhibits isomerization of 9-cis,12-cis-octadecadienoate
Linoleyl hydroxamate
-
inhibits isomerization of 9-cis,12-cis-octadecadienoate
Linoleyl methyl ether
-
inhibits isomerization of 9-cis,12-cis-octadecadienoate
Linoleyl methyl ketone
-
weak inhibition
Linoleyl oxime
-
inhibits isomerization of 9-cis,12-cis-octadecadienoate
methyl linoleate
-
weak inhibition
methyl oleate
-
inhibits isomerization of 9-cis,12-cis-octadecadienoate
o-phenanthroline
-
10% residual activity at 3 mM
oleic acid
-
75% inhibition at 0.02 mM
oleyl alcohol
-
inhibits isomerization of 9-cis,12-cis-octadecadienoate
oleyl amine
-
inhibits isomerization of 9-cis,12-cis-octadecadienoate
p-hydroxymercuribenzoate
-
-
palmitoleic acid
-
72% inhibition at 0.02 mM
stearidonic acid
-
substrate inhibition at concentrations above 0.120 mM
trans-11-Octadecen-9-ynoic acid
-
inhibits isomerization of 9-cis,12-cis-octadecadienoate
trans-3,cis-5-Octadecadienoic acid
-
inhibits isomerization of 2,5-octadecadienoic acid
trans-9,cis-12-Octadecadienoic acid
-
inhibits isomerization of 9-cis,12-cis-octadecadienoate
trans-9,trans-12-Octadecadienoic acid
-
inhibits isomerization of 9-cis,12-cis-octadecadienoate
additional information
-
no effects by DTT, ATP, ADP, NAD+, NADH, NADPH or CoA
-
EDTA
-
reversible
EDTA
-
93% residual activity at 3 mM
linoleic acid
-
substrate inhibition at concentrations above 0.02 mM, some linoleic acid derivatives also inhibited the isomerase
linoleic acid
-
inhibits bacterial growth of strain B24
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biotechnology
-
the enzyme can be useful for biocatalysis of linoleic acid to conjugated linoleic acid
biotechnology
-
the enzyme can be useful for biocatalysis of linoleic acid to conjugated linoleic acid
biotechnology
-
the enzyme can be useful for biocatalysis of linoleic acid to conjugated linoleic acid
-
synthesis
-
the enzyme can be useful for biocatalysis of linoleic acid to conjugated linoleic acid
synthesis
-
the enzyme can be useful for biocatalysis of linoleic acid to conjugated linoleic acid
synthesis
-
method for converting plant oil into a specific conjugated linoleic acid using a synergistic biocatalytic system based on immobilized Propionibacterium acnes linoleate isomerase and Rhizopus oryzae lipase. Using linoleate isomerase immobilized on D301R anion-exchange resin, under optimal conditions up to 109 g/l trans-10,cis-12-linoleic acid are obtained after incubation of 200 g/l sunflower oil. The conversion ratio of linoleic acid to conjugated linoleic acid is 90.5%
synthesis
-
production of trans-10,cis-12-linoleic acid as a single isomer by expression of a fusion construct with enhanced green fluorescent protein on the surface of yeast cells. Upon optimization, a maximum yield of trans-10,cis-12-linoleic acid of 4 mg/ml is observed within 20 h using the strain as whole-cell biocatalyst
synthesis
AX062088
production of trans-10,cis-12-linoleic acid by codon-optimized expression in Mortierella alpina. In presence of 5 microM long-chain acyl-CoA synthetase inhibitor the trans-10,cis-12-linoleic acid content reaches up to 29 mg/l
synthesis
strain Lactobacillus plantarum ZS2058 is able to convert over 50% of linoleic acid to cis-9,trans-11-linoleate and trans9,trans-linoleate. Some intermediates 10-hydroxy-cis-12-octadecenoic acid, 10-oxo-cis-12-octadecenoic acid and 10-oxo-trans-11-octadecenoic acid are found. Expression of the genes coding the multicomponent linoleate isomerase containing myosin-cross-reactive antigen, short-chain dehydrogenase/oxidoreductase and acetoacetate decarboxylase in Escherichia coli leads to the synthesis of cis9,trans-11-linoleate and three kinds of intermediates
synthesis
-
strain Lactobacillus plantarum ZS2058 is able to convert over 50% of linoleic acid to cis-9,trans-11-linoleate and trans9,trans-linoleate. Some intermediates 10-hydroxy-cis-12-octadecenoic acid, 10-oxo-cis-12-octadecenoic acid and 10-oxo-trans-11-octadecenoic acid are found. Expression of the genes coding the multicomponent linoleate isomerase containing myosin-cross-reactive antigen, short-chain dehydrogenase/oxidoreductase and acetoacetate decarboxylase in Escherichia coli leads to the synthesis of cis9,trans-11-linoleate and three kinds of intermediates
-
synthesis
-
the enzyme can be useful for biocatalysis of linoleic acid to conjugated linoleic acid
-
synthesis
-
production of trans-10,cis-12-linoleic acid as a single isomer by expression of a fusion construct with enhanced green fluorescent protein on the surface of yeast cells. Upon optimization, a maximum yield of trans-10,cis-12-linoleic acid of 4 mg/ml is observed within 20 h using the strain as whole-cell biocatalyst
-
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Garcia, P.T.; Christie, W.W.; Jenkin, H.M.; Anderson, L.; Holman, R.T.
The isomerization of 2,5- and 9,12-octadecadienoic acids by an extract of Butyrivibrio fibrisolvens
Biochim. Biophys. Acta
424
296-302
1976
Butyrivibrio fibrisolvens
brenda
Kepler, C.R.; Tucker, W.P.; Tove, S.B.
Biohydrogenation of unsaturated fatty acids. IV. Substrate specificity and inhibition of linoleateDELTA12-cis,DELTA11-trans-isomerase from Butyrivibrio fibrisolvens
J. Biol. Chem.
245
3612-3620
1970
Butyrivibrio fibrisolvens
brenda
Kepler, C.R.; Tove, S.B.
Biohydrogenation of unsaturated fatty acids. III, Purification and properties of a linoleateDELTA12-cis,DELTA11-trans-isomerase from Butyrivibrio fibrisolvens
J. Biol. Chem.
242
5686-5692
1967
Butyrivibrio fibrisolvens
brenda
Fukuda, S.; Furuya, H.; Suzuki, Y.; Asanuma, N.; Hino, T.
A new strain of Butyrivibrio fibrisolvens that has high ability to isomerize linoleic acid to conjugated linoleic acid
J. Gen. Appl. Microbiol.
51
105-113
2005
Butyrivibrio fibrisolvens, Butyrivibrio fibrisolvens TH1
brenda
Peng, S.S.; Deng, M.; Grund, A.D.; Rosson, R.A.
Purification and characterization of a membrane-bound linoleic acid isomerase from Clostridium sporogenes
Enzyme Microb. Technol.
40
831-839
2007
Clostridium sporogenes
-
brenda
Koppova, I.; Lukas, F.; Kopecny, J.
Effect of fatty acids on growth of conjugated-linoleic-acids-producing bacteria in rumen
Folia Microbiol. (Praha)
51
291-293
2006
Pseudobutyrivibrio xylanivorans, Butyrivibrio hungatei, Pseudobutyrivibrio ruminis, Butyrivibrio hungatei A38, Pseudobutyrivibrio xylanivorans JW11
brenda
Irmak, S.; Dunford, N.T.; Gilliland, S.E.; Banskalieva, V.; Eisenmenger, M.
Biocatalysis of linoleic acid to conjugated linoleic acid
Lipids
41
771-776
2006
Lactobacillus acidophilus, Limosilactobacillus reuteri, Lactobacillus acidophilus L1
brenda
Liavonchanka, A.; Feussner, I.
Biochemistry of PUFA double bond isomerases producing conjugated linoleic acid
ChemBioChem
9
1867-1872
2008
Butyrivibrio fibrisolvens, Lactobacillus acidophilus (Q307I4)
brenda
Vasta, V.; Makkar, H.; Mele, M.; Priolo, A.
Ruminal biohydrogenation as affected by tannins in vitro
Br. J. Nutr.
102
82-92
2009
Bacteria
brenda
Macouzet, M.; Robert, N.; Lee, B.H.
Genetic and functional aspects of linoleate isomerase in Lactobacillus acidophilus
Appl. Microbiol. Biotechnol.
87
1737-1742
2010
Lactobacillus acidophilus, Lactobacillus acidophilus ATCC 55739
brenda
You, Q.; Yin, X.; Gu, X.; Xu, H.; Sang, L.
Purification, immobilization and characterization of linoleic acid isomerase on modified palygorskite
Bioprocess Biosyst. Eng.
34
757-765
2011
Lactobacillus delbrueckii subsp. bulgaricus, Lactobacillus delbrueckii subsp. bulgaricus 1.1480
brenda
Kishino, S.; Ogawa, J.; Yokozeki, K.; Shimizu, S.
Linoleic acid isomerase in Lactobacillus plantarum AKU1009a proved to be a multi-component enzyme system requiring oxidoreduction cofactors
Biosci. Biotechnol. Biochem.
75
318-322
2011
Lactiplantibacillus plantarum, Lactiplantibacillus plantarum AKU1009a
brenda
Macouzet, M.; Lee, B.H.; Robert, N.
Genetic and structural comparison of linoleate isomerases from selected food-grade bacteria
J. Appl. Microbiol.
109
2128-2134
2010
Limosilactobacillus reuteri, Limosilactobacillus reuteri ATCC 55739
brenda
Gorissen, L.; Weckx, S.; Vlaeminck, B.; Raes, K.; De Vuyst, L.; De Smet, S.; Leroy, F.
Linoleate isomerase activity occurs in lactic acid bacteria strains and is affected by pH and temperature
J. Appl. Microbiol.
111
593-606
2011
Lactiplantibacillus plantarum (F0V4E8), Lactiplantibacillus plantarum, Latilactobacillus sakei (F0V4F4), Latilactobacillus sakei, Latilactobacillus curvatus (F0V5Y1), Latilactobacillus curvatus, Latilactobacillus sakei LMG 13558 (F0V4F4), Lactiplantibacillus plantarum ATCC 8014 (F0V4E8), Latilactobacillus curvatus LMG 13553 (F0V5Y1)
brenda
He, X.; Shang, J.; Li, F.; Liu, H.
Yeast cell surface display of linoleic acid isomerase from Propionibacterium acnes and its application for the production of trans-10, cis-12 conjugated linoleic acid
Biotechnol. Appl. Biochem.
62
1-8
2015
Cutibacterium acnes, Cutibacterium acnes ATCC 6919
brenda
Hao, D.; Chen, H.; Hao, G.; Yang, B.; Zhang, B.; Zhang, H.; Chen, W.; Chen, Y.Q.
Production of conjugated linoleic acid by heterologous expression of linoleic acid isomerase in oleaginous fungus Mortierella alpina
Biotechnol. Lett.
37
1983-1992
2015
Cutibacterium acnes (AX062088), Cutibacterium acnes
brenda
Fibinger, M.; Freiherr von Sass, G.; Herrfurth, C.; Feussner, I.; Bornscheuer, U.
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Fusarium graminearum, Fusarium graminearum ATCC MYA-4620
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