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Literature summary extracted from

  • Gorina, S.S.; Toporkova, Y.Y.; Mukhtarova, L.S.; Smirnova, E.O.; Chechetkin, I.R.; Khairutdinov, B.I.; Gogolev, Y.V.; Grechkin, A.N.
    Oxylipin biosynthesis in spikemoss Selaginella moellendorffii molecular cloning and identification of divinyl ether synthases CYP74M1and CYP74M3 (2016), Biochim. Biophys. Acta, 1861, 301-309 .
    View publication on PubMed

Cloned(Commentary)

EC Number Cloned (Comment) Organism
4.2.1.B6 gene CYP74M1 , DNA and amino acid sequence determination and analysis, sequence comparisons and unrooted phylogenetic tree, recombinant expression in Escherichia coli strain BL21(DE3)pLysS Selaginella moellendorffii
4.2.1.B8 gene CYP74M1 , DNA and amino acid sequence determination and analysis, sequence comparisons and unrooted phylogenetic tree, recombinant expression in Escherichia coli strain Rosetta-gami(DE3)pLysS B Selaginella moellendorffii

KM Value [mM]

EC Number KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
4.2.1.B6 0.0114
-
(9Z,11E,13S,15Z)-13-hydroperoxy-9,11,15-octadecatrienoic acid pH 7.5, 25°C, recombinant enzyme Selaginella moellendorffii
4.2.1.B6 0.0703
-
(9Z,11E,13S)-13-hydroperoxy-9,11-octadecadienoic acid pH 7.5, 25°C, recombinant enzyme Selaginella moellendorffii
4.2.1.B8 0.0723
-
(9Z,11E,13S)-13-hydroperoxy-9,11-octadecadienoic acid pH 7.5, 25°C, recombinant enzyme Selaginella moellendorffii
4.2.1.B8 0.0893
-
(9Z,11E,13S,15Z)-13-hydroperoxy-9,11,15-octadecatrienoic acid pH 7.5, 25°C, recombinant enzyme Selaginella moellendorffii

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
4.2.1.B6 (9Z,11E,13S)-13-hydroperoxy-9,11-octadecadienoic acid Selaginella moellendorffii i.e. 13-HPOD (9Z,11E)-12[(1E)-hex-1-en-1-yloxy]dodeca-9,11-dienoic acid + H2O
-
?
4.2.1.B6 (9Z,11E,13S,15Z)-13-hydroperoxy-9,11,15-octadecatrienoic acid Selaginella moellendorffii i.e. 13-HPOT (9Z,11E)-12[(1Z,3Z)-hexa-1,3-dien-1-yloxy]dodeca-9,11-dienoic acid + H2O
-
?
4.2.1.B8 (9Z,11E,13S)-13-hydroperoxy-9,11-octadecadienoic acid Selaginella moellendorffii i.e. 13-HPOD (9Z,11E)-12[(1E)-hex-1-en-1-yloxy]dodeca-9,11-dienoic acid + H2O
-
?
4.2.1.B8 (9Z,11E,13S,15Z)-13-hydroperoxy-9,11,15-octadecatrienoic acid Selaginella moellendorffii i.e. 13-HPOT (9Z,11E)-12[(1Z,3Z)-hexa-1,3-dien-1-yloxy]dodeca-9,11-dienoic acid + H2O
-
?

Organism

EC Number Organism UniProt Comment Textmining
4.2.1.B6 Selaginella moellendorffii D8S724
-
-
4.2.1.B8 Selaginella moellendorffii D8QZ31
-
-

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
4.2.1.B6 (9Z,11E,13S)-13-hydroperoxy-9,11-octadecadienoic acid i.e. 13-HPOD Selaginella moellendorffii (9Z,11E)-12[(1E)-hex-1-en-1-yloxy]dodeca-9,11-dienoic acid + H2O
-
?
4.2.1.B6 (9Z,11E,13S,15Z)-13-hydroperoxy-9,11,15-octadecatrienoic acid i.e. 13-HPOT Selaginella moellendorffii (9Z,11E)-12[(1Z,3Z)-hexa-1,3-dien-1-yloxy]dodeca-9,11-dienoic acid + H2O
-
?
4.2.1.B6 additional information products are analyzed by gas chromatography-mass spectrometry, Individual oxylipins are purified by HPLC and finally identified by their NMR data, including the 1H NMR, 2D-COSY, HSQC and HMBC, overview. Enzyme CYP74M1 (SmDES1) specifically converts 13-HPOT to (11Z)-etherolenic acid and 13-HPOD to (11Z)-etheroleic acid via a (Z)-vinyl ether radial intermediate. The enzyme is inactive towards (9S,10E,12Z,15Z)-9-hydroperoxy-10,12,15-octadecatrienoic acid (9-HPOT) and (9S,10E,12Z)-9-hydroperoxy-10,12-octadecadienoic acid (9-HPOD) Selaginella moellendorffii ?
-
?
4.2.1.B8 (9Z,11E,13S)-13-hydroperoxy-9,11-octadecadienoic acid i.e. 13-HPOD Selaginella moellendorffii (9Z,11E)-12[(1E)-hex-1-en-1-yloxy]dodeca-9,11-dienoic acid + H2O
-
?
4.2.1.B8 (9Z,11E,13S,15Z)-13-hydroperoxy-9,11,15-octadecatrienoic acid i.e. 13-HPOT Selaginella moellendorffii (9Z,11E)-12[(1Z,3Z)-hexa-1,3-dien-1-yloxy]dodeca-9,11-dienoic acid + H2O
-
?
4.2.1.B8 additional information products are analyzed by gas chromatography-mass spectrometry, individual oxylipins are purified by HPLC and finally identified by their NMR data, including the 1H NMR, 2D-COSY, HSQC and HMBC, overview. Enzyme CYP74M3 (SmDES2) converts 13-HPOT and 13-HPOD mainly to etherolenic and etheroleic acids, respectively, via an (E)-vinyl ether radial intermediate. The enzyme is inactive towards (9S,10E,12Z,15Z)-9-hydroperoxy-10,12,15-octadecatrienoic acid (9-HPOT) and (9S,10E,12Z)-9-hydroperoxy-10,12-octadecadienoic acid (9-HPOD) Selaginella moellendorffii ?
-
?

Synonyms

EC Number Synonyms Comment Organism
4.2.1.B6 CYP74M1
-
Selaginella moellendorffii
4.2.1.B6 SmDES1
-
Selaginella moellendorffii
4.2.1.B8 CYP74M3
-
Selaginella moellendorffii
4.2.1.B8 SmDES2
-
Selaginella moellendorffii

Temperature Optimum [°C]

EC Number Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
4.2.1.B6 25
-
assay at Selaginella moellendorffii
4.2.1.B8 25
-
assay at Selaginella moellendorffii

Turnover Number [1/s]

EC Number Turnover Number Minimum [1/s] Turnover Number Maximum [1/s] Substrate Comment Organism Structure
4.2.1.B6 185.3
-
(9Z,11E,13S,15Z)-13-hydroperoxy-9,11,15-octadecatrienoic acid pH 7.5, 25°C, recombinant enzyme Selaginella moellendorffii
4.2.1.B6 261.1
-
(9Z,11E,13S)-13-hydroperoxy-9,11-octadecadienoic acid pH 7.5, 25°C, recombinant enzyme Selaginella moellendorffii
4.2.1.B8 193.5
-
(9Z,11E,13S)-13-hydroperoxy-9,11-octadecadienoic acid pH 7.5, 25°C, recombinant enzyme Selaginella moellendorffii
4.2.1.B8 266.7
-
(9Z,11E,13S,15Z)-13-hydroperoxy-9,11,15-octadecatrienoic acid pH 7.5, 25°C, recombinant enzyme Selaginella moellendorffii

pH Optimum

EC Number pH Optimum Minimum pH Optimum Maximum Comment Organism
4.2.1.B6 7.5
-
assay at Selaginella moellendorffii
4.2.1.B8 7.5
-
assay at Selaginella moellendorffii

kcat/KM [mM/s]

EC Number kcat/KM Value [1/mMs-1] kcat/KM Value Maximum [1/mMs-1] Substrate Comment Organism Structure
4.2.1.B6 3714.1
-
(9Z,11E,13S)-13-hydroperoxy-9,11-octadecadienoic acid pH 7.5, 25°C, recombinant enzyme Selaginella moellendorffii
4.2.1.B6 16254.4
-
(9Z,11E,13S,15Z)-13-hydroperoxy-9,11,15-octadecatrienoic acid pH 7.5, 25°C, recombinant enzyme Selaginella moellendorffii
4.2.1.B8 2676.3
-
(9Z,11E,13S)-13-hydroperoxy-9,11-octadecadienoic acid pH 7.5, 25°C, recombinant enzyme Selaginella moellendorffii
4.2.1.B8 2986.6
-
(9Z,11E,13S,15Z)-13-hydroperoxy-9,11,15-octadecatrienoic acid pH 7.5, 25°C, recombinant enzyme Selaginella moellendorffii