EC
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1.14.13.151
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Transferred entry: | linalool 8-monooxygenase. Now EC 1.14.14.84, linalool 8-monooxygenase
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[EC 1.14.13.151 created 1989 as EC 1.14.99.28, transferred 2012 to EC 1.14.13.151, deleted 2018] |
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EC
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1.14.13.152
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Transferred entry: | geraniol 8-hydroxylase. Now EC 1.14.14.83, geraniol 8-hydroxylase
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[EC 1.14.13.152 created 2012, deleted 2018] |
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EC |
1.14.14.58 |
Accepted name: |
trimethyltridecatetraene synthase |
Reaction: |
(6E,10E)-geranyllinalool + [reduced NADPH—hemoprotein reductase] + O2 = (3E,7E)-4,8,12-trimethyltrideca-1,3,7,11-tetraene + [oxidized NADPH—hemoprotein reductase] + but-3-en-2-one + 2 H2O |
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For diagram of acyclic diterpenoid biosynthesis, click here |
Glossary: |
(6E,10E)-geranyllinalool = (6E,10E)-3,7,11,15-tetramethylhexadeca-1,6,10,14-tetraen-3-ol |
Other name(s): |
CYP82G1; CYP92C5; CYP92C6; DMNT/TMTT homoterpene synthase |
Systematic name: |
(6E,10E)-geranyllinalool,[reduced NADPH—hemoprotein reductase]:oxygen oxidoreductase |
Comments: |
A cytochrome P-450 (heme-thiolate) protein isolated from the plants Arabidopsis thaliana (thale cress) and Zea mays (maize). It forms this C16 homoterpene in response to herbivore attack. In vitro some variants of the enzyme also convert (3S,6E)-nerolidol to (3E)-4,8-dimethylnona-1,3,7-triene (see EC 1.14.14.59, dimethylnonatriene synthase). |
Links to other databases: |
BRENDA, EXPASY, KEGG, MetaCyc |
References: |
1. |
Lee, S., Badieyan, S., Bevan, D.R., Herde, M., Gatz, C. and Tholl, D. Herbivore-induced and floral homoterpene volatiles are biosynthesized by a single P450 enzyme (CYP82G1) in Arabidopsis. Proc. Natl. Acad. Sci. USA 107 (2010) 21205–21210. [DOI] [PMID: 21088219] |
2. |
Richter, A., Schaff, C., Zhang, Z., Lipka, A.E., Tian, F., Kollner, T.G., Schnee, C., Preiss, S., Irmisch, S., Jander, G., Boland, W., Gershenzon, J., Buckler, E.S. and Degenhardt, J. Characterization of biosynthetic pathways for the production of the volatile homoterpenes DMNT and TMTT in Zea mays. Plant Cell 28 (2016) 2651–2665. [DOI] [PMID: 27662898] |
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[EC 1.14.14.58 created 2018] |
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EC |
1.14.14.59 |
Accepted name: |
dimethylnonatriene synthase |
Reaction: |
(3S,6E)-nerolidol + [reduced NADPH—hemoprotein reductase] + O2 = (3E)-4,8-dimethylnona-1,3,7-triene + [oxidized NADPH—hemoprotein reductase] + but-3-en-2-one + 2 H2O |
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For diagram of acyclic sesquiterpenoid biosynthesis, click here |
Other name(s): |
CYP82G1; CYP92C5; DMNT/TMTT homoterpene synthase |
Systematic name: |
(3S,6E)-nerolidol,[reduced NADPH—hemoprotein reductase]:oxygen oxidoreductase |
Comments: |
A cytochrome P-450 (heme-thiolate) protein isolated from the plants Arabidopsis thaliana (thale cress) and Zea mays (maize). It forms this C11 homoterpene in response to herbivore attack. In vitro the enzyme also converts (6E,10E)-geranyllinalool to (3E,7E)-4,8,12-trimethyltrideca-1,3,7,11-tetraene (see EC 1.14.14.58, trimethyltridecatetraene synthase). |
Links to other databases: |
BRENDA, EXPASY, KEGG, MetaCyc |
References: |
1. |
Lee, S., Badieyan, S., Bevan, D.R., Herde, M., Gatz, C. and Tholl, D. Herbivore-induced and floral homoterpene volatiles are biosynthesized by a single P450 enzyme (CYP82G1) in Arabidopsis. Proc. Natl. Acad. Sci. USA 107 (2010) 21205–21210. [DOI] [PMID: 21088219] |
2. |
Richter, A., Schaff, C., Zhang, Z., Lipka, A.E., Tian, F., Kollner, T.G., Schnee, C., Preiss, S., Irmisch, S., Jander, G., Boland, W., Gershenzon, J., Buckler, E.S. and Degenhardt, J. Characterization of biosynthetic pathways for the production of the volatile homoterpenes DMNT and TMTT in Zea mays. Plant Cell 28 (2016) 2651–2665. [DOI] [PMID: 27662898] |
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[EC 1.14.14.59 created 2018] |
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EC |
1.14.14.83 |
Accepted name: |
geraniol 8-hydroxylase |
Reaction: |
geraniol + [reduced NADPH—hemoprotein reductase] + O2 = (6E)-8-hydroxygeraniol + [oxidized NADPH—hemoprotein reductase] + H2O |
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For diagram of acyclic monoterpenoid biosynthesis, click here |
Other name(s): |
CYP76B6 (gene name); G10H (gene name) |
Systematic name: |
geraniol,[reduced NADPH—hemoprotein reductase]:oxygen oxidoreductase (8-hydroxylating) |
Comments: |
A cytochrome P-450 (heme thiolate) protein found in plants. Also hydroxylates nerol and citronellol, cf. EC 1.14.14.84, linalool 8-monooxygenase. The recommended numbering of geraniol gives 8-hydroxygeraniol as the product rather than 10-hydroxygeraniol as used by references 1-3. See prenol nomenclature Pr-1. The cloned enzyme also catalysed, but less efficiently, the 3′-hydroxylation of naringenin (cf. EC 1.14.14.82, flavonoid 3′-monooxygenase) [3]. |
Links to other databases: |
BRENDA, EXPASY, KEGG, MetaCyc |
References: |
1. |
Collu, G., Unver, N., Peltenburg-Looman, A.M., van der Heijden, R., Verpoorte, R. and Memelink, J. Geraniol 10-hydroxylase, a cytochrome P450 enzyme involved in terpenoid indole alkaloid biosynthesis. FEBS Lett. 508 (2001) 215–220. [DOI] [PMID: 11718718] |
2. |
Wang, J., Liu, Y., Cai, Y., Zhang, F., Xia, G. and Xiang, F. Cloning and functional analysis of geraniol 10-hydroxylase, a cytochrome P450 from Swertia mussotii Franch. Biosci. Biotechnol. Biochem. 74 (2010) 1583–1590. [PMID: 20699579] |
3. |
Sung, P.H., Huang, F.C., Do, Y.Y. and Huang, P.L. Functional expression of geraniol 10-hydroxylase reveals its dual function in the biosynthesis of terpenoid and phenylpropanoid. J. Agric. Food Chem. 59 (2011) 4637–4643. [DOI] [PMID: 21504162] |
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[EC 1.14.14.83 created 2012 as EC 1.14.13.152, transferred 2018 to EC 1.14.14.83] |
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EC |
1.14.14.84 |
Accepted name: |
linalool 8-monooxygenase |
Reaction: |
linalool + 2 [reduced NADPH—hemoprotein reductase] + 2 O2 = (6E)-8-oxolinalool + 2 [oxidized NADPH—hemoprotein reductase] + 3 H2O (overall reaction) (1a) linalool + [reduced NADPH—hemoprotein reductase] + O2 = (6E)-8-hydroxylinalool + [oxidized NADPH—hemoprotein reductase] + H2O (1b) (6E)-8-hydroxylinalool + [reduced NADPH—hemoprotein reductase] + O2 = (6E)-8-oxolinalool + [oxidized NADPH—hemoprotein reductase] + 2 H2O |
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For diagram of acyclic monoterpenoid biosynthesis, click here |
Glossary: |
linalool = 3,7-dimethylocta-1,6-dien-3-ol |
Other name(s): |
P-450lin; CYP111 |
Systematic name: |
linalool,[reduced NADPH—hemoprotein reductase]:oxygen oxidoreductase (8-hydroxylating) |
Comments: |
A cytochrome P-450 (heme-thiolate) protein found in plants. The secondary electron donor is a specific [2Fe-2S] ferredoxin from the same bacterial strain. |
Links to other databases: |
BRENDA, EXPASY, KEGG, MetaCyc |
References: |
1. |
Ullah, A.J., Murray, R.I., Bhattacharyya, P.K., Wagner, G.C. and Gunsalus, I.C. Protein components of a cytochrome P-450 linalool 8-methyl hydroxylase. J. Biol. Chem. 265 (1990) 1345–1351. [PMID: 2295633] |
2. |
Ropp, J.D., Gunsalus, I.C. and Sligar, S.G. Cloning and expression of a member of a new cytochrome P-450 family: cytochrome P-450lin (CYP111) from Pseudomonas incognita. J. Bacteriol. 175 (1993) 6028–6037. [DOI] [PMID: 8376348] |
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[EC 1.14.14.84 created 1989 as EC 1.14.99.28, transferred 2012 to EC 1.14.13.151, transferred 2018 to EC 1.14.14.84] |
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EC
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1.14.99.28
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Transferred entry: | linalool 8-monooxygenase. Now EC 1.14.14.84, linalool 8-monooxygenase
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[EC 1.14.99.28 created 1989, deleted 2012] |
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EC |
4.2.1.127 |
Accepted name: |
linalool dehydratase |
Reaction: |
(3S)-linalool = myrcene + H2O |
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For diagram of acyclic monoterpenoid biosynthesis, click here |
Glossary: |
linalool = 3,7-dimethylocta-1,6-dien-3-ol |
Other name(s): |
linalool hydro-lyase (myrcene-forming) |
Systematic name: |
(3S)-linalool hydro-lyase (myrcene-forming) |
Comments: |
In absence of oxygen the bifunctional linalool dehydratase-isomerase can catalyse in vitro two reactions, the hydration of myrcene to (3S)-linalool and the isomerization of (3S)-linalool to geraniol, the latter activity being classified as EC 5.4.4.4, geraniol isomerase. |
Links to other databases: |
BRENDA, EXPASY, KEGG, MetaCyc, PDB |
References: |
1. |
Brodkorb, D., Gottschall, M., Marmulla, R., Lüddeke, F. and Harder, J. Linalool dehydratase-isomerase, a bifunctional enzyme in the anaerobic degradation of monoterpenes. J. Biol. Chem. 285 (2010) 30436–30442. [DOI] [PMID: 20663876] |
2. |
Lüddeke, F. and Harder, J. Enantiospecific (S)-(+)-linalool formation from β-myrcene by linalool dehydratase-isomerase. Z. Naturforsch. C 66 (2011) 409–412. [PMID: 21950166] |
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[EC 4.2.1.127 created 2011, modified 2012] |
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EC |
4.2.3.25 |
Accepted name: |
S-linalool synthase |
Reaction: |
geranyl diphosphate + H2O = (3S)-linalool + diphosphate |
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For diagram of acyclic monoterpenoid biosynthesis, click here |
Glossary: |
(3S)-linalool = (3S)-3,7-dimethylocta-1,6-dien-3-ol |
Other name(s): |
LIS; Lis; 3S-linalool synthase |
Systematic name: |
geranyl-diphosphate diphosphate-lyase [(3S)-linalool-forming] |
Comments: |
Requires Mn2+ or Mg2+ for activity. Neither (S)- nor (R)-linalyl diphosphate can act as substrate for the enzyme from the flower Clarkia breweri [1]. Unlike many other monoterpene synthases, only a single product, (3S)-linalool, is formed. |
Links to other databases: |
BRENDA, EXPASY, KEGG, MetaCyc, CAS registry number: 160477-81-6 |
References: |
1. |
Pichersky, E., Lewinsohn, E. and Croteau, R. Purification and characterization of S-linalool synthase, an enzyme
involved in the production of floral scent in Clarkia breweri. Arch. Biochem. Biophys. 316 (1995) 803–807. [DOI] [PMID: 7864636] |
2. |
Lücker, J., Bouwmeester, H.J., Schwab, W., Blaas, J., van der Plas, L.H. and Verhoeven, H.A. Expression of Clarkia S-linalool synthase in transgenic petunia plants results in the accumulation of S-linalyl-β-D-glucopyranoside. Plant J. 27 (2001) 315–324. [DOI] [PMID: 11532177] |
3. |
Dudareva, N., Cseke, L., Blanc, V.M. and Pichersky, E. Evolution of floral scent in Clarkia: novel patterns of S-linalool synthase gene expression in the C. breweri flower. Plant Cell 8 (1996) 1137–1148. [DOI] [PMID: 8768373] |
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[EC 4.2.3.25 created 2006] |
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EC |
4.2.3.26 |
Accepted name: |
R-linalool synthase |
Reaction: |
geranyl diphosphate + H2O = (3R)-linalool + diphosphate |
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For diagram of acyclic monoterpenoid biosynthesis, click here |
Glossary: |
(3R)-linalool = (3R)-3,7-dimethylocta-1,6-dien-3-ol |
Other name(s): |
(3R)-linalool synthase; (–)-3R-linalool synthase |
Systematic name: |
geranyl-diphosphate diphosphate-lyase [(3R)-linalool-forming] |
Comments: |
Geranyl diphosphate cannot be replaced by isopentenyl diphosphate (3-methylbut-3-en-1-yl diphosphate), prenyl diphosphate, farnesyl diphosphate or geranylgeranyl diphosphate as substrate [1]. Requires Mg2+ or Mn2+ for activity. Unlike many other monoterpene synthases, only a single product, (3R)-linalool, is formed. |
Links to other databases: |
BRENDA, EXPASY, KEGG, MetaCyc, PDB, CAS registry number: 254993-26-5 |
References: |
1. |
Jia, J.W., Crock, J., Lu, S., Croteau, R. and Chen, X.Y. (3R)-Linalool synthase from Artemisia annua L.: cDNA isolation,
characterization, and wound induction. Arch. Biochem. Biophys. 372 (1999) 143–149. [DOI] [PMID: 10562427] |
2. |
Crowell, A.L., Williams, D.C., Davis, E.M., Wildung, M.R. and Croteau, R. Molecular cloning and characterization of a new linalool synthase. Arch. Biochem. Biophys. 405 (2002) 112–121. [DOI] [PMID: 12176064] |
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[EC 4.2.3.26 created 2006] |
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EC |
4.2.3.144 |
Accepted name: |
geranyllinalool synthase |
Reaction: |
geranylgeranyl diphosphate + H2O = (6E,10E)-geranyllinalool + diphosphate |
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For diagram of acyclic diterpenoid biosynthesis, click here |
Glossary: |
geranylgeranyl diphosphate = (2E,6E,10E)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-yl diphosphate
(6E,10E)-geranyllinalool = (6E,10E)-3,7,11,15-tetramethylhexadeca-1,6,10,14-tetraen-3-ol |
Other name(s): |
TPS04/GES; GES |
Systematic name: |
geranylgeranyl-diphosphate diphosphate-lyase [(E,E)-geranyllinalool-forming] |
Comments: |
The enzyme is a component of the herbivore-induced indirect defense system. The product, (E,E)-geranyllinalool, is a precursor to the volatile compound 4,8,12-trimethyl-1,3,7,11-tridecatetraene (TMTT), which is released by many plants in response to damage. |
Links to other databases: |
BRENDA, EXPASY, KEGG, MetaCyc |
References: |
1. |
Herde, M., Gartner, K., Kollner, T.G., Fode, B., Boland, W., Gershenzon, J., Gatz, C. and Tholl, D. Identification and regulation of TPS04/GES, an Arabidopsis geranyllinalool synthase catalyzing the first step in the formation of the insect-induced volatile C16-homoterpene TMTT. Plant Cell 20 (2008) 1152–1168. [DOI] [PMID: 18398052] |
2. |
Attaran, E., Rostas, M. and Zeier, J. Pseudomonas syringae elicits emission of the terpenoid (E,E)-4,8,12-trimethyl-1,3,7,11-tridecatetraene in Arabidopsis leaves via jasmonate signaling and expression of the terpene synthase TPS4. Mol. Plant Microbe Interact. 21 (2008) 1482–1497. [DOI] [PMID: 18842097] |
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[EC 4.2.3.144 created 2013] |
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EC |
5.4.4.4 |
Accepted name: |
geraniol isomerase |
Reaction: |
geraniol = (3S)-linalool |
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For diagram of acyclic monoterpenoid biosynthesis, click here |
Systematic name: |
geraniol hydroxymutase |
Comments: |
In absence of oxygen the bifunctional linalool dehydratase-isomerase can catalyse in vitro two reactions, the isomerization of (3S)-linalool to geraniol and the hydration of myrcene to (3S)-linalool, the latter activity being classified as EC 4.2.1.127, linalool dehydratase. |
Links to other databases: |
BRENDA, EXPASY, KEGG, MetaCyc, PDB |
References: |
1. |
Brodkorb, D., Gottschall, M., Marmulla, R., Lüddeke, F. and Harder, J. Linalool dehydratase-isomerase, a bifunctional enzyme in the anaerobic degradation of monoterpenes. J. Biol. Chem. 285 (2010) 30436–30442. [DOI] [PMID: 20663876] |
2. |
Lüddeke, F. and Harder, J. Enantiospecific (S)-(+)-linalool formation from β-myrcene by linalool dehydratase-isomerase. Z. Naturforsch. C 66 (2011) 409–412. [PMID: 21950166] |
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[EC 5.4.4.4 created 2011, modified 2012] |
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EC |
5.4.4.8 |
Accepted name: |
linalool isomerase |
Reaction: |
(RS)-linalool = geraniol
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For diagram of acyclic monoterpenoid biosynthesis, click here |
Other name(s): |
3,1-hydroxyl-Δ1-Δ2-mutase (linalool isomerase) |
Systematic name: |
(RS)-linalool hydroxymutase |
Comments: |
Isolated from the bacterium Thauera linaloolentis grown on (RS)-linalool as the sole source of carbon. Unlike EC 5.4.4.4, geraniol isomerase, which only acts on (S)-linalool, this enzyme acts equally well on both enantiomers. |
Links to other databases: |
BRENDA, EXPASY, KEGG, MetaCyc |
References: |
1. |
Marmulla, R., Šafarić, B., Markert, S., Schweder, T. and Harder, J. Linalool isomerase, a membrane-anchored enzyme in the anaerobic monoterpene degradation in Thauera linaloolentis 47Lol. BMC Biochem. 17:6 (2016). [DOI] [PMID: 26979141] |
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[EC 5.4.4.8 created 2017] |
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