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Literature summary for 1.14.14.80 extracted from

  • Huang, F.; Peter, A.; Schwab, W.
    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 .
    View publication on PubMedView publication on EuropePMC

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