| EC |
4.2.1.121 |
| Accepted name: |
colneleate synthase |
| Reaction: |
(9S,10E,12Z)-9-hydroperoxyoctadeca-10,12-dienoate = (8E)-9-[(1E,3Z)-nona-1,3-dien-1-yloxy]non-8-enoate + H2O |
| Glossary: |
colneleate = (8E)-9-[(1E,3Z)-nona-1,3-dien-1-yloxy]non-8-enoate |
| Other name(s): |
9-divinyl ether synthase; 9-DES; CYP74D; CYP74D1; CYP74 cytochrome P-450; DES1; (8E)-9-[(1E,3E)-nona-1,3-dien-1-yloxy]non-8-enoate synthase |
| Systematic name: |
(9S,10E,12Z)-9-hydroperoxyoctadeca-10,12-dienoate hydro-lyase |
| Comments: |
A heme-thiolate protein (P-450) [2]. It catalyses the selective removal of pro-R hydrogen at C-8 in the biosynthesis of colneleic acid [4]. It forms also (8E)-9-[(1E,3Z,6Z)-nona-1,3,6-trien-1-yloxy]non-8-enoic acid (i.e. colnelenate) from (9S,10E,12Z,15Z)-9-hydroperoxy-10,12,15-octadecatrienoate. The corresponding 13-hydroperoxides are poor substrates [1,3]. The divinyl ethers colneleate and colnelenate have antimicrobial activity. |
| Links to other databases: |
BRENDA, EXPASY, KEGG, MetaCyc |
| References: |
| 1. |
Stumpe, M., Kandzia, R., Gobel, C., Rosahl, S. and Feussner, I. A pathogen-inducible divinyl ether synthase (CYP74D) from elicitor-treated potato suspension cells. FEBS Lett. 507 (2001) 371–376. [DOI] [PMID: 11696374] |
| 2. |
Itoh, A. and Howe, G.A. Molecular cloning of a divinyl ether synthase. Identification as a CYP74 cytochrome P-450. J. Biol. Chem. 276 (2001) 3620–3627. [DOI] [PMID: 11060314] |
| 3. |
Fammartino, A., Cardinale, F., Gobel, C., Mene-Saffrane, L., Fournier, J., Feussner, I. and Esquerre-Tugaye, M.T. Characterization of a divinyl ether biosynthetic pathway specifically associated with pathogenesis in tobacco. Plant Physiol. 143 (2007) 378–388. [DOI] [PMID: 17085514] |
| 4. |
Hamberg, M. Hidden stereospecificity in the biosynthesis of divinyl ether fatty acids. FEBS J. 272 (2005) 736–743. [DOI] [PMID: 15670154] |
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| [EC 4.2.1.121 created 2011, modified 2014] |
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| EC |
4.2.1.183 |
| Accepted name: |
etheroleic acid synthase |
| Reaction: |
(9Z,11E,13S)-13-hydroperoxy-9,11-octadecadienoate = (9Z,11E)-12-[(1E)-hex-1-en-1-yloxy]dodeca-9,11-dienoate + H2O |
| Glossary: |
(9Z,11E)-12-[(1E)-hex-1-en-1-yloxy]dodeca-9,11-dienoic acid = etheroleic acid
(9Z,11E,13S)-13-hydroperoxy-9,11-octadecadienoic acid = 13(S)-HPOD |
| Other name(s): |
colneleic acid/etheroleic acid synthase; 13/9-DES; 9/13-DES; 13/9-divinyl ether synthase; (9Z,11E)-12-[(1E)-hex-1-en-1-yloxy]dodeca-9,11-dienoate synthase |
| Systematic name: |
(9Z,11E,13S)-13-hydroperoxy-9,11-octadecadienoate lyase |
| Comments: |
A heme-thiolate protein (P-450) occurring in several plants, including Allium sativum (garlic) and Selaginella moellendorffii (spikemoss). The enzyme also catalyses the reaction of EC 4.2.1.121, colneleate synthase, to a lesser extent. |
| Links to other databases: |
BRENDA, EXPASY, KEGG, MetaCyc |
| References: |
| 1. |
Grechkin, A.N., Fazliev, F.N. and Mukhtarova, L.S. The lipoxygenase pathway in garlic (Allium sativum L.) bulbs: detection of the novel divinyl ether oxylipins. FEBS Lett. 371 (1995) 159–162. [DOI] [PMID: 7672118] |
| 2. |
Stumpe, M., Carsjens, J.G., Gobel, C. and Feussner, I. Divinyl ether synthesis in garlic bulbs. J. Exp. Bot. 59 (2008) 907–915. [DOI] [PMID: 18326559] |
| 3. |
Gorina, S.S., Toporkova, Y.Y., Mukhtarova, L.S., Smirnova, E.O., Chechetkin, I.R., Khairutdinov, B.I., Gogolev, Y.V. and Grechkin, A.N. Oxylipin biosynthesis in spikemoss Selaginella moellendorffii: Molecular cloning and identification of divinyl ether synthases CYP74M1 and CYP74M3. Biochim. Biophys Acta 1861 (2016) 301–309. [DOI] [PMID: 26776054] |
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| [EC 4.2.1.183 created 2024] |
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