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Literature summary for 5.4.4.6 extracted from

  • Seo, M.J.; Kang, W.R.; Shin, K.C.; Oh, D.K.
    Production of 7,8-dihydroxy unsaturated fatty acids from plant oils by whole recombinant cells expressing 7,8-linoleate diol synthase from Glomerella cingulata (2016), J. Agric. Food Chem., 64, 8555-8562 .
    View publication on PubMed

Activating Compound

Activating Compound Comment Organism Structure
DMSO activates the whole enzyme activity Colletotrichum gloeosporioides

Cloned(Commentary)

Cloned (Comment) Organism
recombinant expression of His-tagged enzyme in Escherichia coli strain ER2566 Colletotrichum gloeosporioides

Protein Variants

Protein Variants Comment Organism
additional information reaction conditions for the production of (7S,8S,9Z,12Z)-dihydroxyoctadeca-9,12-dienoic acid from linoleic acid by recombinant Escherichia coli expressing 7,8-linoleate diol synthase from Glomerella cingulata are optimized using response surface methodology, overview. The optimal reaction conditions are pH 7.0, 18.6°C, 10.8% v/v dimethyl sulfoxide, 44.9 g/l cells, and 14.3 g/l linoleic acid, with agitation at 256 rpm. Under these conditions, recombinant cells produce 7,8-dihydroxy unsaturated fatty acids in the range of 7.0-9.8 g/l from 14.3 g/l linoleic acid, 14.3 g/l oleic acid, and plant oil hydrolysates such as waste oil and olive oil containing 14.3 g/l linoleic acid or oleic acid. Comparisons of quantitative production of dihydroxy unsaturated fatty acids by microorganisms Colletotrichum gloeosporioides

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
(8R,9Z,12Z)-8-hydroperoxyoctadeca-9,12-dienoate Colletotrichum gloeosporioides
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(7S,8S,9Z,12Z)-7,8-dihydroxyoctadeca-9,12-dienoate
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r

Organism

Organism UniProt Comment Textmining
Colletotrichum gloeosporioides A0A0S2SWE4 i.e. Colletotrichum gloeosporioides
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Colletotrichum gloeosporioides KACC 40961 A0A0S2SWE4 i.e. Colletotrichum gloeosporioides
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Purification (Commentary)

Purification (Comment) Organism
recombinant His-tagged wild-enzyme from Escherichia coli strain ER2566 by nickel affinity chromatography Colletotrichum gloeosporioides

Source Tissue

Source Tissue Comment Organism Textmining
mycelium
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Colletotrichum gloeosporioides
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Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
(8R,9Z,12Z)-8-hydroperoxyoctadeca-9,12-dienoate
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Colletotrichum gloeosporioides (7S,8S,9Z,12Z)-7,8-dihydroxyoctadeca-9,12-dienoate
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r
(8R,9Z,12Z)-8-hydroperoxyoctadeca-9,12-dienoate isomerase reaction of the C-terminal domain Colletotrichum gloeosporioides (7S,8S,9Z,12Z)-7,8-dihydroxyoctadeca-9,12-dienoate
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r
(9Z)-8-hydroperoxyoctadeca-9-enoic acid isomerase reaction of the C-terminal domain Colletotrichum gloeosporioides (9Z)-7,8-dihydroxyoctadeca-9-enoic acid
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r
(9Z,12Z,15Z)-8-hydroperoxyoctadeca-9,12,15-trienoic acid isomerase reaction of the C-terminal domain Colletotrichum gloeosporioides (9Z,12Z,15Z)-7,8-dihydroxyoctadeca-9,12,15-trienoic acid
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r
alpha-linolenate + O2 via (9Z,12Z,15Z)-8-hydroperoxyoctadeca-9,12,15-trienoic acid, whole enzyme reaction Colletotrichum gloeosporioides (9Z,12Z,15Z)-7,8-dihydroperoxyoctadeca-9,12,15-trienoic acid
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?
linoleate via (8R,9Z,12Z)-8-hydroperoxyoctadeca-9,12-dienoate, whole enzyme reaction, best substrate Colletotrichum gloeosporioides (7S,8S,9Z,12Z)-7,8-dihydroxyoctadeca-9,12-dienoate
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r
additional information the bifunctional enzyme converts linoleic acid to a product, identified as (9Z,12Z)-7,8-dihydroxyoctadeca-9,12-dienoic acid (7,8-DiHODE) by liquid chromatography-mass spectrometry/mass spectrometry (LC-MS/MS) and nuclear magnetic resonance (NMR) spectroscopy. The specific activity and catalytic efficiency (kcat/Km) of 7,8-diol synthase for the conversion of fatty acid to dihydroxy fatty acid follows the descending order linoleic acid, alpha-linolenic acid, and oleic acid, indicating that the enzyme is a 7,8-linoleate diol synthase (7,8-LDS). The reaction via (9Z,12Z)-8-hydroperoxyoctadeca-9,12-dienoic acid (8-HPODE) as an intermediate and the accumulation of 8-HPODE is due to a higher 8-dioxygenase activity in the N-terminal domain than hydroperoxide isomerase activity in the C-terminal domain, EC 5.4.4.6. 8-HPODE is subsequently isomerized to (7S,8S,9Z,12Z)-dihydroxyoctadeca-9,12-dienoic acid (7,8-DiHODE) or (5S,8R,9Z,12Z)-dihydroxyoctadeca-9,12-dienoic acid (5,8-DiHODE) by the C-terminal hydroperoxide isomerase domain of diol synthase Colletotrichum gloeosporioides ?
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?
oleate + O2 via (9Z)-8-hydroperoxyoctadeca-9-enoic acid, whole enzyme reaction Colletotrichum gloeosporioides (9Z)-7,8-dihydroxyoctadeca-9-enoic acid
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?

Synonyms

Synonyms Comment Organism
7,8-diol synthase
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Colletotrichum gloeosporioides
7,8-LDS
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Colletotrichum gloeosporioides
7,8-linoleate diol synthase
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Colletotrichum gloeosporioides

Temperature Optimum [°C]

Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
37
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assay at Colletotrichum gloeosporioides

pH Optimum

pH Optimum Minimum pH Optimum Maximum Comment Organism
7.5
-
assay at Colletotrichum gloeosporioides