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Literature summary extracted from
- 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 .
Activating Compound
| EC Number | Activating Compound | Comment | Organism | Structure |
|---|---|---|---|---|
| 1.13.11.60 | DMSO | activates the whole enzyme activity | Colletotrichum gloeosporioides |  |
| 5.4.4.6 | DMSO | activates the whole enzyme activity | Colletotrichum gloeosporioides | |
Application
| EC Number | Application | Comment | Organism |
|---|---|---|---|
| 1.13.11.60 | synthesis | production of (7S,8S)-7,8-dihydroxy-(9Z,12Z)-octadecadienoic acid from linoleic acid by recombinant Escherichia coli. 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 | Colletotrichum gloeosporioides |
Cloned(Commentary)
| EC Number | Cloned (Comment) | Organism |
|---|---|---|
| 1.13.11.60 | expression in Escherichia coli | Colletotrichum gloeosporioides |
| 1.13.11.60 | recombinant expression of His-tagged enzyme in Escherichia coli strain ER2566 | Colletotrichum gloeosporioides |
| 5.4.4.6 | recombinant expression of His-tagged enzyme in Escherichia coli strain ER2566 | Colletotrichum gloeosporioides |
Protein Variants
| EC Number | Protein Variants | Comment | Organism |
|---|---|---|---|
| 1.13.11.60 | 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. 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 |
| 5.4.4.6 | 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)
| EC Number | Natural Substrates | Organism | Comment (Nat. Sub.) | Natural Products | Comment (Nat. Pro.) | Rev. | Reac. |
|---|---|---|---|---|---|---|---|
| 1.13.11.60 | linoleate + O2 | Colletotrichum gloeosporioides | - |
(8R,9Z,12Z)-8-hydroperoxyoctadeca-9,12-dienoate | - |
? | |
| 1.13.11.60 | linoleate + O2 | Colletotrichum gloeosporioides KACC 40961 | - |
(8R,9Z,12Z)-8-hydroperoxyoctadeca-9,12-dienoate | - |
? | |
| 5.4.4.6 | (8R,9Z,12Z)-8-hydroperoxyoctadeca-9,12-dienoate | Colletotrichum gloeosporioides | - |
(7S,8S,9Z,12Z)-7,8-dihydroxyoctadeca-9,12-dienoate | - |
r | |
Organism
| EC Number | Organism | UniProt | Comment | Textmining |
|---|---|---|---|---|
| 1.13.11.60 | Colletotrichum gloeosporioides | A0A0S2SWE4 | i.e. Colletotrichum gloeosporioides | - |
| 1.13.11.60 | Colletotrichum gloeosporioides | A0A0S2SWE4 | bifunctional enzyme, the second domain isomerizes the product (8R,9Z,12Z)-8-hydroperoxyoctadeca-9,12-dienoate to (7S,8S,9Z,12Z)-5,8-dihydroxyoctadeca-9,12-dienoate, cf. EC 5.4.4.6 | - |
| 1.13.11.60 | Colletotrichum gloeosporioides KACC 40961 | A0A0S2SWE4 | i.e. Colletotrichum gloeosporioides | - |
| 5.4.4.6 | Colletotrichum gloeosporioides | A0A0S2SWE4 | i.e. Colletotrichum gloeosporioides | - |
| 5.4.4.6 | Colletotrichum gloeosporioides KACC 40961 | A0A0S2SWE4 | i.e. Colletotrichum gloeosporioides | - |
Purification (Commentary)
| EC Number | Purification (Comment) | Organism |
|---|---|---|
| 1.13.11.60 | recombinant His-tagged wild-enzyme from Escherichia coli strain ER2566 by nickel affinity chromatography | Colletotrichum gloeosporioides |
| 5.4.4.6 | recombinant His-tagged wild-enzyme from Escherichia coli strain ER2566 by nickel affinity chromatography | Colletotrichum gloeosporioides |
Source Tissue
| EC Number | Source Tissue | Comment | Organism | Textmining |
|---|---|---|---|---|
| 1.13.11.60 | mycelium | - |
Colletotrichum gloeosporioides | - |
| 5.4.4.6 | mycelium | - |
Colletotrichum gloeosporioides | - |
Substrates and Products (Substrate)
| EC Number | Substrates | Comment Substrates | Organism | Products | Comment (Products) | Rev. | Reac. |
|---|---|---|---|---|---|---|---|
| 1.13.11.60 | alpha-linolenate + O2 | via (9Z,12Z,15Z)-8-hydroperoxyoctadeca-9,12,15-trienoate, whole enzyme reaction | Colletotrichum gloeosporioides | (9Z,12Z,15Z)-7,8-dihydroperoxyoctadeca-9,12,15-trienoate | - |
? | |
| 1.13.11.60 | alpha-linolenate + O2 | dioxygenase reaction of the N-terminal domain | Colletotrichum gloeosporioides | (9Z,12Z,15Z)-8-hydroperoxyoctadeca-9,12,15-trienoate | - |
? | |
| 1.13.11.60 | 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 | - |
r | |
| 1.13.11.60 | linoleate | via (8R,9Z,12Z)-8-hydroperoxyoctadeca-9,12-dienoate, whole enzyme reaction, best substrate | Colletotrichum gloeosporioides KACC 40961 | (7S,8S,9Z,12Z)-7,8-dihydroxyoctadeca-9,12-dienoate | - |
r | |
| 1.13.11.60 | linoleate + O2 | - |
Colletotrichum gloeosporioides | (8R,9Z,12Z)-8-hydroperoxyoctadeca-9,12-dienoate | - |
? | |
| 1.13.11.60 | linoleate + O2 | dioxygenase reaction of the N-terminal domain | Colletotrichum gloeosporioides | (8R,9Z,12Z)-8-hydroperoxyoctadeca-9,12-dienoate | - |
? | |
| 1.13.11.60 | linoleate + O2 | - |
Colletotrichum gloeosporioides KACC 40961 | (8R,9Z,12Z)-8-hydroperoxyoctadeca-9,12-dienoate | - |
? | |
| 1.13.11.60 | linoleate + O2 | dioxygenase reaction of the N-terminal domain | Colletotrichum gloeosporioides KACC 40961 | (8R,9Z,12Z)-8-hydroperoxyoctadeca-9,12-dienoate | - |
? | |
| 1.13.11.60 | linoleate + O2 | - |
Colletotrichum gloeosporioides | (7S,8S)-7,8-dihydroxy-(9Z,12Z)-octadecadienoic acid | - |
? | |
| 1.13.11.60 | linoleate + O2 | - |
Colletotrichum gloeosporioides KACC 40961 | (7S,8S)-7,8-dihydroxy-(9Z,12Z)-octadecadienoic acid | - |
? | |
| 1.13.11.60 | 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 | ? | - |
? | |
| 1.13.11.60 | 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 KACC 40961 | ? | - |
? | |
| 1.13.11.60 | oleate + O2 | via (9Z)-8-hydroperoxyoctadeca-9-enoic acid, whole enzyme reaction | Colletotrichum gloeosporioides | (9Z)-7,8-dihydroxyoctadeca-9-enoic acid | - |
? | |
| 1.13.11.60 | oleate + O2 | dioxygenase reaction of the N-terminal domain | Colletotrichum gloeosporioides | (9Z)-8-hydroperoxyoctadeca-9-enoic acid | - |
? | |
| 5.4.4.6 | (8R,9Z,12Z)-8-hydroperoxyoctadeca-9,12-dienoate | - |
Colletotrichum gloeosporioides | (7S,8S,9Z,12Z)-7,8-dihydroxyoctadeca-9,12-dienoate | - |
r | |
| 5.4.4.6 | (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 | - |
r | |
| 5.4.4.6 | (9Z)-8-hydroperoxyoctadeca-9-enoic acid | isomerase reaction of the C-terminal domain | Colletotrichum gloeosporioides | (9Z)-7,8-dihydroxyoctadeca-9-enoic acid | - |
r | |
| 5.4.4.6 | (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 | - |
r | |
| 5.4.4.6 | 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 | - |
? | |
| 5.4.4.6 | 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 | - |
r | |
| 5.4.4.6 | 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 | ? | - |
? | |
| 5.4.4.6 | oleate + O2 | via (9Z)-8-hydroperoxyoctadeca-9-enoic acid, whole enzyme reaction | Colletotrichum gloeosporioides | (9Z)-7,8-dihydroxyoctadeca-9-enoic acid | - |
? | |
Synonyms
| EC Number | Synonyms | Comment | Organism |
|---|---|---|---|
| 1.13.11.60 | 7,8-diol synthase | - |
Colletotrichum gloeosporioides |
| 1.13.11.60 | 7,8-LDS | - |
Colletotrichum gloeosporioides |
| 1.13.11.60 | 7,8-linoleate diol synthase | - |
Colletotrichum gloeosporioides |
| 5.4.4.6 | 7,8-diol synthase | - |
Colletotrichum gloeosporioides |
| 5.4.4.6 | 7,8-LDS | - |
Colletotrichum gloeosporioides |
| 5.4.4.6 | 7,8-linoleate diol synthase | - |
Colletotrichum gloeosporioides |
Temperature Optimum [°C]
| EC Number | Temperature Optimum [°C] | Temperature Optimum Maximum [°C] | Comment | Organism |
|---|---|---|---|---|
| 1.13.11.60 | 37 | - |
assay at | Colletotrichum gloeosporioides |
| 5.4.4.6 | 37 | - |
assay at | Colletotrichum gloeosporioides |
pH Optimum
| EC Number | pH Optimum Minimum | pH Optimum Maximum | Comment | Organism |
|---|---|---|---|---|
| 1.13.11.60 | 7.5 | - |
assay at | Colletotrichum gloeosporioides |
| 5.4.4.6 | 7.5 | - |
assay at | Colletotrichum gloeosporioides |
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