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Literature summary for 1.14.14.80 extracted from
- Expression and characterization of CYP52 genes involved in the biosynthesis of sophorolipid and alkane metabolism from Starmerella bombicola (2014), Appl. Environ. Microbiol., 80, 766-776 .
Cloned(Commentary)
| Cloned (Comment) | Organism |
|---|---|
| gene CYP52E3, DNA and amino acid sequence determination and analysis, recombinant expression in Saccharomyces cerevisiae strains WAT11 and and INVSc1 | Starmerella bombicola |
| gene CYP52M1, DNA and amino acid sequence determination and analysis, recombinant expression in Saccharomyces cerevisiae strains WAT11 and and INVSc1. 17-Hydroxy linoleic acid is detected in addition to 18-carboxy linoleic acid (cis-9, cis-12-octadecadien-1,18-dioic acid) in the reaction mixture of linoleic acid with CYP52M1-transformed cells | Starmerella bombicola |
| gene CYP52N1, DNA and amino acid sequence determination and analysis, recombinant expression in Saccharomyces cerevisiae strains WAT11 and and INVSc1 | Starmerella bombicola |
KM Value [mM]
| KM Value [mM] | KM Value Maximum [mM] | Substrate | Comment | Organism | Structure |
|---|---|---|---|---|---|
| 0.04 | - |
oleic acid | pH 7.0, 30°C, recombinant enzyme | Starmerella bombicola |  |
| 0.046 | - |
arachidonic acid | pH 7.0, 30°C, recombinant enzyme | Starmerella bombicola | |
| 0.068 | - |
linoleic acid | pH 7.0, 30°C, recombinant enzyme | Starmerella bombicola | |
Localization
| Localization | Comment | Organism | GeneOntology No. | Textmining |
|---|---|---|---|---|
| microsome | - |
Starmerella bombicola | - |
- |
Natural Substrates/ Products (Substrates)
| Natural Substrates | Organism | Comment (Nat. Sub.) | Natural Products | Comment (Nat. Pro.) | Rev. | Reac. |
|---|---|---|---|---|---|---|
| alpha-linolenic acid + [reduced NADPH-hemoprotein reductase] + O2 | Starmerella bombicola | low activity | 18-hydroxylinolenic acid + [oxidized NADPH-hemoprotein reductase] + H2O | - |
? | |
| alpha-linolenic acid + [reduced NADPH-hemoprotein reductase] + O2 | Starmerella bombicola ATCC 22214 | low activity | 18-hydroxylinolenic acid + [oxidized NADPH-hemoprotein reductase] + H2O | - |
? | |
| arachidonic acid + [reduced NADPH-hemoprotein reductase] + O2 | Starmerella bombicola | - |
20-hydroxyarachidonic acid + [oxidized NADPH-hemoprotein reductase] + H2O | - |
? | |
| arachidonic acid + [reduced NADPH-hemoprotein reductase] + O2 | Starmerella bombicola ATCC 22214 | - |
20-hydroxyarachidonic acid + [oxidized NADPH-hemoprotein reductase] + H2O | - |
? | |
| linoleic acid + [reduced NADPH-hemoprotein reductase] + O2 | Starmerella bombicola | - |
18-hydroxylinoleic acid + [oxidized NADPH-hemoprotein reductase] + H2O | - |
? | |
| linoleic acid + [reduced NADPH-hemoprotein reductase] + O2 | Starmerella bombicola ATCC 22214 | - |
18-hydroxylinoleic acid + [oxidized NADPH-hemoprotein reductase] + H2O | - |
? | |
| additional information | Starmerella bombicola | enzyme CYP52E3 minor omega-hydroxylation activity against myristic acid, palmitic acid, palmitoleic acid, and oleic acid. Transformation efficiency of fatty acids into glucolipids by CYP52M1/UGTA1 is much higher than those by CYP52N1/UGTA1 and CYP52E3/UGTA1 in Starmerella bombicola | ? | - |
? | |
| additional information | Starmerella bombicola | enzyme CYP52M1 oxidizes C16 to C20 fatty acids preferentially. It converts oleic acid (C18:1) more efficiently than stearic acid (C18:0) and linoleic acid (C18:2) and much more effectively than linolenic acid (C18:3). No products are detected when C10 to C12 fatty acids are used as the substrates. CYP52M1 hydroxylates fatty acids at their omega and omega-1 positions. Transformation efficiency of fatty acids into glucolipids by CYP52M1/UGTA1 is much higher than those by CYP52N1/UGTA1 and CYP52E3/UGTA1 in Starmerella bombicola | ? | - |
? | |
| additional information | Starmerella bombicola | enzyme CYP52N1 oxidizes C14 to C20 saturated and unsaturated fatty acids and preferentially oxidizes palmitic acid, oleic acid, and linoleic acid. It only catalyzes omega-hydroxylation of fatty acids. Transformation efficiency of fatty acids into glucolipids by CYP52M1/UGTA1 is much higher than those by CYP52N1/UGTA1 and CYP52E3/UGTA1 in Starmerella bombicola | ? | - |
? | |
| additional information | Starmerella bombicola ATCC 22214 | enzyme CYP52M1 oxidizes C16 to C20 fatty acids preferentially. It converts oleic acid (C18:1) more efficiently than stearic acid (C18:0) and linoleic acid (C18:2) and much more effectively than linolenic acid (C18:3). No products are detected when C10 to C12 fatty acids are used as the substrates. CYP52M1 hydroxylates fatty acids at their omega and omega-1 positions. Transformation efficiency of fatty acids into glucolipids by CYP52M1/UGTA1 is much higher than those by CYP52N1/UGTA1 and CYP52E3/UGTA1 in Starmerella bombicola | ? | - |
? | |
| additional information | Starmerella bombicola ATCC 22214 | enzyme CYP52E3 minor omega-hydroxylation activity against myristic acid, palmitic acid, palmitoleic acid, and oleic acid. Transformation efficiency of fatty acids into glucolipids by CYP52M1/UGTA1 is much higher than those by CYP52N1/UGTA1 and CYP52E3/UGTA1 in Starmerella bombicola | ? | - |
? | |
| additional information | Starmerella bombicola ATCC 22214 | enzyme CYP52N1 oxidizes C14 to C20 saturated and unsaturated fatty acids and preferentially oxidizes palmitic acid, oleic acid, and linoleic acid. It only catalyzes omega-hydroxylation of fatty acids. Transformation efficiency of fatty acids into glucolipids by CYP52M1/UGTA1 is much higher than those by CYP52N1/UGTA1 and CYP52E3/UGTA1 in Starmerella bombicola | ? | - |
? | |
| myristic acid + [reduced NADPH-hemoprotein reductase] + O2 | Starmerella bombicola | - |
14-hydroxymyristic acid + [oxidized NADPH-hemoprotein reductase] + H2O | - |
? | |
| myristic acid + [reduced NADPH-hemoprotein reductase] + O2 | Starmerella bombicola ATCC 22214 | - |
14-hydroxymyristic acid + [oxidized NADPH-hemoprotein reductase] + H2O | - |
? | |
| oleic acid + [reduced NADPH-hemoprotein reductase] + O2 | Starmerella bombicola | - |
18-hydroxyoleic acid + [oxidized NADPH-hemoprotein reductase] + H2O | - |
? | |
| oleic acid + [reduced NADPH-hemoprotein reductase] + O2 | Starmerella bombicola | best substrate | 18-hydroxyoleic acid + [oxidized NADPH-hemoprotein reductase] + H2O | - |
? | |
| oleic acid + [reduced NADPH-hemoprotein reductase] + O2 | Starmerella bombicola ATCC 22214 | best substrate | 18-hydroxyoleic acid + [oxidized NADPH-hemoprotein reductase] + H2O | - |
? | |
| oleic acid + [reduced NADPH-hemoprotein reductase] + O2 | Starmerella bombicola ATCC 22214 | - |
18-hydroxyoleic acid + [oxidized NADPH-hemoprotein reductase] + H2O | - |
? | |
| palmitic acid + [reduced NADPH-hemoprotein reductase] + O2 | Starmerella bombicola | - |
16-hydroxypalmitic acid + [oxidized NADPH-hemoprotein reductase] + H2O | - |
? | |
| palmitic acid + [reduced NADPH-hemoprotein reductase] + O2 | Starmerella bombicola ATCC 22214 | - |
16-hydroxypalmitic acid + [oxidized NADPH-hemoprotein reductase] + H2O | - |
? | |
| palmitoleic acid + [reduced NADPH-hemoprotein reductase] + O2 | Starmerella bombicola | - |
18-hydroxypalmitoleic acid + [oxidized NADPH-hemoprotein reductase] + H2O | - |
? | |
| palmitoleic acid + [reduced NADPH-hemoprotein reductase] + O2 | Starmerella bombicola | - |
16-hydroxypalmitoleic acid + [oxidized NADPH-hemoprotein reductase] + H2O | - |
? | |
| stearic acid + [reduced NADPH-hemoprotein reductase] + O2 | Starmerella bombicola | - |
18-hydroxystearic acid + [oxidized NADPH-hemoprotein reductase] + H2O | - |
? | |
Organism
| Organism | UniProt | Comment | Textmining |
|---|---|---|---|
| Starmerella bombicola | B8QHP1 | formerly Candida bombicola | - |
| Starmerella bombicola | B8QHP3 | formerly Candida bombicola | - |
| Starmerella bombicola | B8QHP5 | formerly Candida bombicola | - |
| Starmerella bombicola ATCC 22214 | B8QHP1 | formerly Candida bombicola | - |
| Starmerella bombicola ATCC 22214 | B8QHP3 | formerly Candida bombicola | - |
| Starmerella bombicola ATCC 22214 | B8QHP5 | formerly Candida bombicola | - |
Purification (Commentary)
| Purification (Comment) | Organism |
|---|---|
| native enzyme partially by isolation of microsomes | Starmerella bombicola |
Substrates and Products (Substrate)
| Substrates | Comment Substrates | Organism | Products | Comment (Products) | Rev. | Reac. |
|---|---|---|---|---|---|---|
| alpha-linolenic acid + [reduced NADPH-hemoprotein reductase] + O2 | low activity | Starmerella bombicola | 18-hydroxylinolenic acid + [oxidized NADPH-hemoprotein reductase] + H2O | - |
? | |
| alpha-linolenic acid + [reduced NADPH-hemoprotein reductase] + O2 | low activity | Starmerella bombicola ATCC 22214 | 18-hydroxylinolenic acid + [oxidized NADPH-hemoprotein reductase] + H2O | - |
? | |
| arachidonic acid + [reduced NADPH-hemoprotein reductase] + O2 | - |
Starmerella bombicola | 20-hydroxyarachidonic acid + [oxidized NADPH-hemoprotein reductase] + H2O | - |
? | |
| arachidonic acid + [reduced NADPH-hemoprotein reductase] + O2 | - |
Starmerella bombicola ATCC 22214 | 20-hydroxyarachidonic acid + [oxidized NADPH-hemoprotein reductase] + H2O | - |
? | |
| cis-9,10-epoxystearic acid + [reduced NADPH-hemoprotein reductase] + O2 | - |
Starmerella bombicola | 18-hydroxy-cis-9,10-epoxystearic acid + [oxidized NADPH-hemoprotein reductase] + H2O | - |
? | |
| linoleic acid + [reduced NADPH-hemoprotein reductase] + O2 | - |
Starmerella bombicola | 18-hydroxylinoleic acid + [oxidized NADPH-hemoprotein reductase] + H2O | - |
? | |
| linoleic acid + [reduced NADPH-hemoprotein reductase] + O2 | - |
Starmerella bombicola ATCC 22214 | 18-hydroxylinoleic acid + [oxidized NADPH-hemoprotein reductase] + H2O | - |
? | |
| additional information | enzyme CYP52E3 minor omega-hydroxylation activity against myristic acid, palmitic acid, palmitoleic acid, and oleic acid. Transformation efficiency of fatty acids into glucolipids by CYP52M1/UGTA1 is much higher than those by CYP52N1/UGTA1 and CYP52E3/UGTA1 in Starmerella bombicola | Starmerella bombicola | ? | - |
? | |
| additional information | enzyme CYP52M1 oxidizes C16 to C20 fatty acids preferentially. It converts oleic acid (C18:1) more efficiently than stearic acid (C18:0) and linoleic acid (C18:2) and much more effectively than linolenic acid (C18:3). No products are detected when C10 to C12 fatty acids are used as the substrates. CYP52M1 hydroxylates fatty acids at their omega and omega-1 positions. Transformation efficiency of fatty acids into glucolipids by CYP52M1/UGTA1 is much higher than those by CYP52N1/UGTA1 and CYP52E3/UGTA1 in Starmerella bombicola | Starmerella bombicola | ? | - |
? | |
| additional information | enzyme CYP52N1 oxidizes C14 to C20 saturated and unsaturated fatty acids and preferentially oxidizes palmitic acid, oleic acid, and linoleic acid. It only catalyzes omega-hydroxylation of fatty acids. Transformation efficiency of fatty acids into glucolipids by CYP52M1/UGTA1 is much higher than those by CYP52N1/UGTA1 and CYP52E3/UGTA1 in Starmerella bombicola | Starmerella bombicola | ? | - |
? | |
| additional information | in coassays with glucosyltransferase UGTA1, UGTA1 glycosylates all hydroxyl fatty acids generated by CYP52E3. Product identification und quantification by LC-MS and GC-MS. CYP52E3 displays activity in the resting cell system but not in the in vitro system. No formation of 17-hydroxy linoleic acid. No activity with stearic acid, linoleic acid, alpha-linolenic acid, cis-11-eicosenoic acid, arachidonic acid, hexadecane, octadecane, capric acid, and lauric acid | Starmerella bombicola | ? | - |
? | |
| additional information | in coassays with glucosyltransferase UGTA1, UGTA1 glycosylates all hydroxyl fatty acids generated by CYP52N1 Product identification und quantification by LC-MS and GC-MS. CYP52N1 displays activity in the resting cell system but not in the in vitro system. No activity with hexadecane, octadecane, capric acid, lauric acid, and cis-11-eicosenoic acid | Starmerella bombicola | ? | - |
? | |
| additional information | no activity with C10 to C12 fatty acids, myristic acid is a poor substrate, also no activity with hexadecane, octadecane, capric acid, lauric acid, and cis-11-eicosenoic acid. In coassays with glucosyltransferase UGTA1, UGTA1 glycosylates all hydroxyl fatty acids generated by CYP52M1. Product identification und quantification by LC-MS and GC-MS | Starmerella bombicola | ? | - |
? | |
| additional information | enzyme CYP52M1 oxidizes C16 to C20 fatty acids preferentially. It converts oleic acid (C18:1) more efficiently than stearic acid (C18:0) and linoleic acid (C18:2) and much more effectively than linolenic acid (C18:3). No products are detected when C10 to C12 fatty acids are used as the substrates. CYP52M1 hydroxylates fatty acids at their omega and omega-1 positions. Transformation efficiency of fatty acids into glucolipids by CYP52M1/UGTA1 is much higher than those by CYP52N1/UGTA1 and CYP52E3/UGTA1 in Starmerella bombicola | Starmerella bombicola ATCC 22214 | ? | - |
? | |
| additional information | no activity with C10 to C12 fatty acids, myristic acid is a poor substrate, also no activity with hexadecane, octadecane, capric acid, lauric acid, and cis-11-eicosenoic acid. In coassays with glucosyltransferase UGTA1, UGTA1 glycosylates all hydroxyl fatty acids generated by CYP52M1. Product identification und quantification by LC-MS and GC-MS | Starmerella bombicola ATCC 22214 | ? | - |
? | |
| additional information | enzyme CYP52E3 minor omega-hydroxylation activity against myristic acid, palmitic acid, palmitoleic acid, and oleic acid. Transformation efficiency of fatty acids into glucolipids by CYP52M1/UGTA1 is much higher than those by CYP52N1/UGTA1 and CYP52E3/UGTA1 in Starmerella bombicola | Starmerella bombicola ATCC 22214 | ? | - |
? | |
| additional information | in coassays with glucosyltransferase UGTA1, UGTA1 glycosylates all hydroxyl fatty acids generated by CYP52E3. Product identification und quantification by LC-MS and GC-MS. CYP52E3 displays activity in the resting cell system but not in the in vitro system. No formation of 17-hydroxy linoleic acid. No activity with stearic acid, linoleic acid, alpha-linolenic acid, cis-11-eicosenoic acid, arachidonic acid, hexadecane, octadecane, capric acid, and lauric acid | Starmerella bombicola ATCC 22214 | ? | - |
? | |
| additional information | enzyme CYP52N1 oxidizes C14 to C20 saturated and unsaturated fatty acids and preferentially oxidizes palmitic acid, oleic acid, and linoleic acid. It only catalyzes omega-hydroxylation of fatty acids. Transformation efficiency of fatty acids into glucolipids by CYP52M1/UGTA1 is much higher than those by CYP52N1/UGTA1 and CYP52E3/UGTA1 in Starmerella bombicola | Starmerella bombicola ATCC 22214 | ? | - |
? | |
| additional information | in coassays with glucosyltransferase UGTA1, UGTA1 glycosylates all hydroxyl fatty acids generated by CYP52N1 Product identification und quantification by LC-MS and GC-MS. CYP52N1 displays activity in the resting cell system but not in the in vitro system. No activity with hexadecane, octadecane, capric acid, lauric acid, and cis-11-eicosenoic acid | Starmerella bombicola ATCC 22214 | ? | - |
? | |
| myristic acid + [reduced NADPH-hemoprotein reductase] + O2 | - |
Starmerella bombicola | 14-hydroxymyristic acid + [oxidized NADPH-hemoprotein reductase] + H2O | - |
? | |
| myristic acid + [reduced NADPH-hemoprotein reductase] + O2 | - |
Starmerella bombicola ATCC 22214 | 14-hydroxymyristic acid + [oxidized NADPH-hemoprotein reductase] + H2O | - |
? | |
| oleic acid + [reduced NADPH-hemoprotein reductase] + O2 | - |
Starmerella bombicola | 18-hydroxyoleic acid + [oxidized NADPH-hemoprotein reductase] + H2O | - |
? | |
| oleic acid + [reduced NADPH-hemoprotein reductase] + O2 | best substrate | Starmerella bombicola | 18-hydroxyoleic acid + [oxidized NADPH-hemoprotein reductase] + H2O | - |
? | |
| oleic acid + [reduced NADPH-hemoprotein reductase] + O2 | best substrate | Starmerella bombicola ATCC 22214 | 18-hydroxyoleic acid + [oxidized NADPH-hemoprotein reductase] + H2O | - |
? | |
| oleic acid + [reduced NADPH-hemoprotein reductase] + O2 | - |
Starmerella bombicola ATCC 22214 | 18-hydroxyoleic acid + [oxidized NADPH-hemoprotein reductase] + H2O | - |
? | |
| palmitic acid + [reduced NADPH-hemoprotein reductase] + O2 | - |
Starmerella bombicola | 16-hydroxypalmitic acid + [oxidized NADPH-hemoprotein reductase] + H2O | - |
? | |
| palmitic acid + [reduced NADPH-hemoprotein reductase] + O2 | - |
Starmerella bombicola ATCC 22214 | 16-hydroxypalmitic acid + [oxidized NADPH-hemoprotein reductase] + H2O | - |
? | |
| palmitoleic acid + [reduced NADPH-hemoprotein reductase] + O2 | - |
Starmerella bombicola | 18-hydroxypalmitoleic acid + [oxidized NADPH-hemoprotein reductase] + H2O | - |
? | |
| palmitoleic acid + [reduced NADPH-hemoprotein reductase] + O2 | - |
Starmerella bombicola | 16-hydroxypalmitoleic acid + [oxidized NADPH-hemoprotein reductase] + H2O | - |
? | |
| stearic acid + [reduced NADPH-hemoprotein reductase] + O2 | - |
Starmerella bombicola | 18-hydroxystearic acid + [oxidized NADPH-hemoprotein reductase] + H2O | - |
? | |
| trans-9,10-epoxystearic acid + [reduced NADPH-hemoprotein reductase] + O2 | - |
Starmerella bombicola | 18-hydroxy-trans-9,10-epoxystearic acid + [oxidized NADPH-hemoprotein reductase] + H2O | - |
? | |
Synonyms
| Synonyms | Comment | Organism |
|---|---|---|
| CYP52E3 | - |
Starmerella bombicola |
| CYP52M1 | - |
Starmerella bombicola |
| CYP52N1 | - |
Starmerella bombicola |
Temperature Optimum [°C]
| Temperature Optimum [°C] | Temperature Optimum Maximum [°C] | Comment | Organism |
|---|---|---|---|
| 25 | 30 | - |
Starmerella bombicola |
| 30 | - |
assay at | Starmerella bombicola |
pH Optimum
| pH Optimum Minimum | pH Optimum Maximum | Comment | Organism |
|---|---|---|---|
| 7 | - |
- |
Starmerella bombicola |
| 7 | - |
assay at | Starmerella bombicola |
Cofactor
| Cofactor | Comment | Organism | Structure |
|---|---|---|---|
| cytochrome P450 | - |
Starmerella bombicola | |
| NADPH | - |
Starmerella bombicola | |
General Information
| General Information | Comment | Organism |
|---|---|---|
| evolution | the enzyme is a member of the cytochrome P450 monooxygenase CYP52 gene family | Starmerella bombicola |
| metabolism | CYP52M1 is involved in the biosynthesis of sophorolipid | Starmerella bombicola |
| metabolism | enzyme CYP52E3 might be involved in alkane metabolism in Starmerella bombicola but downstream of the initial oxidation steps | Starmerella bombicola |
| metabolism | enzyme CYP52N1 might be involved in alkane metabolism in Starmerella bombicola but downstream of the initial oxidation steps | Starmerella bombicola |
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