1.14.14.58: trimethyltridecatetraene synthase
This is an abbreviated version!
For detailed information about trimethyltridecatetraene synthase, go to the full flat file.
Reaction
Synonyms
At3g25180, CYP82G1, CYP92C5, CYP92C6, cytochrome P450 82G1, DMNT homoterpene synthase, DMNT synthase, DMNT/TMTT homoterpene synthase, TMTT homoterpene synthase, TMTT synthase
ECTree
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Substrates Products
Substrates Products on EC 1.14.14.58 - trimethyltridecatetraene synthase
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REACTION DIAGRAM
(3S)-(E,E)-geranyllinalool + [reduced NADPH-hemoprotein reductase] + O2
(E,E)-4,8,12-trimethyltrideca-1,3,7,11-tetraene + but-1-en-3-one + [oxidized NADPH-hemoprotein reductase] + 2 H2O
(3S,6E)-nerolidol + [reduced NADPH-hemoprotein reductase] + O2
(3E)-4,8-dimethylnona-1,3,7-triene + but-1-en-3-one + [oxidized NADPH-hemoprotein reductase] + 2 H2O
(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
(E)-nerolidol + [reduced NADPH-hemoprotein reductase] + O2
4,8-dimethylnona-1,3,7-triene + but-1-en-3-one + [oxidized NADPH-hemoprotein reductase] + 2 H2O
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?
(E,E)-geranyllinalool + [reduced NADPH-hemoprotein reductase] + O2
(E,E)-4,8,12-trimethyltrideca-1,3,7,11-tetraene + but-1-en-3-one + [oxidized NADPH-hemoprotein reductase] + 2 H2O
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?
arabidiol + [reduced NADPH-hemoprotein reductase] + O2
(3E)-4,8-dimethylnona-1,3,7-triene + ? + [oxidized NADPH-hemoprotein reductase] + 2 H2O
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?
(E,E)-4,8,12-trimethyltrideca-1,3,7,11-tetraene + but-1-en-3-one + [oxidized NADPH-hemoprotein reductase] + 2 H2O
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?
(3S)-(E,E)-geranyllinalool + [reduced NADPH-hemoprotein reductase] + O2
(E,E)-4,8,12-trimethyltrideca-1,3,7,11-tetraene + but-1-en-3-one + [oxidized NADPH-hemoprotein reductase] + 2 H2O
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?
(3S)-(E,E)-geranyllinalool + [reduced NADPH-hemoprotein reductase] + O2
(E,E)-4,8,12-trimethyltrideca-1,3,7,11-tetraene + but-1-en-3-one + [oxidized NADPH-hemoprotein reductase] + 2 H2O
biosynthesis of the volatile organic compound (E,E)-4,8,12-trimethyltrideca-1,3,7,11-tetraene
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?
(3S)-(E,E)-geranyllinalool + [reduced NADPH-hemoprotein reductase] + O2
(E,E)-4,8,12-trimethyltrideca-1,3,7,11-tetraene + but-1-en-3-one + [oxidized NADPH-hemoprotein reductase] + 2 H2O
major substrate
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?
(3S)-(E,E)-geranyllinalool + [reduced NADPH-hemoprotein reductase] + O2
(E,E)-4,8,12-trimethyltrideca-1,3,7,11-tetraene + but-1-en-3-one + [oxidized NADPH-hemoprotein reductase] + 2 H2O
B6ST66, B8A110
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?
(3E)-4,8-dimethylnona-1,3,7-triene + but-1-en-3-one + [oxidized NADPH-hemoprotein reductase] + 2 H2O
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?
(3S,6E)-nerolidol + [reduced NADPH-hemoprotein reductase] + O2
(3E)-4,8-dimethylnona-1,3,7-triene + but-1-en-3-one + [oxidized NADPH-hemoprotein reductase] + 2 H2O
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?
(3S,6E)-nerolidol + [reduced NADPH-hemoprotein reductase] + O2
(3E)-4,8-dimethylnona-1,3,7-triene + but-1-en-3-one + [oxidized NADPH-hemoprotein reductase] + 2 H2O
in vitro activity is 5.3fold higher than with (E,E)-geranyllinalool. (3E)-4,8-dimethylnona-1,3,7-triene is not emitted from Arabidopsis leaves (or only in negligible amounts according to our analysis) because of the absence of a prominent (E)-nerolidol synthase activity in this tissue
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?
(3S,6E)-nerolidol + [reduced NADPH-hemoprotein reductase] + O2
(3E)-4,8-dimethylnona-1,3,7-triene + but-1-en-3-one + [oxidized NADPH-hemoprotein reductase] + 2 H2O
B6ST66, B8A110
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?
(3S,6E)-nerolidol + [reduced NADPH-hemoprotein reductase] + O2
(3E)-4,8-dimethylnona-1,3,7-triene + but-1-en-3-one + [oxidized NADPH-hemoprotein reductase] + 2 H2O
B6ST66, B8A110
major substrate
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?
(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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?
(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
B6ST66, B8A110
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no activity with isophytol, (E)-geraniol, linalool, 3,7,11-trimethyl-3-dodecanol, (Z)-nerolidol. Less than 1% of the activity with (3S,6E)-nerolidol: (E,E,E)-geranylgeraniol, (E,E)-farnesylacetone, (E,E)-farnesol, (E)-geranylacetone. Construction of a protein model based on multiple mammalian P450 templates with closest sequence similarity. Subsequent molecular docking confirms a position of (E)-nerolidol and (E,E)-geranyllinalool in the active site cavity that allows the suggested oxidative bond cleavage reaction to proceed by a syn-elimination (beta-elimination) mechanism. In particular, the carbonyl oxygen of Thr313 in one of the substrate recognition sites appears to be essential for anchoring the substrates by forming a strong hydrogen bond with the hydroxyl group at C3. The model supported the observed differences in substrate specificities
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additional information
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cytochrome P450 monooxygenase with narrow substrate specificity for (E,E)-geranyllinalool and (E)-nerolidol. Mechanism follows oxidative bond cleavage of the alcohol substrate via syn-elimination of the polar head, together with an allylic C-5 hydrogen atom. No substrate: racemic linalool or (R)-(-)-linalool
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additional information
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linalool, (Z)-nerolidol, the primary terpene alcohols (E,E,E)-geranylgeraniol, (E,E)-farnesol, and (E)-geraniol, or fully saturated analogs of (E)-nerolidol and (E,E)-geranyllinalool (3,7,11-trimethyl-3-dodecanol, isophytol) are no functional substrates of the CYP82G1 enzyme
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additional information
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CYP705A1 cleaves the prenyl side chain of arabidiol to produce (E)-4,8-dimethyl-1,3,7-nonatriene, DMNT, and a nonvolatile C19-ketone derivative
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additional information
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CYP705A1 cleaves the prenyl side chain of arabidiol to produce (E)-4,8-dimethyl-1,3,7-nonatriene, DMNT, and a nonvolatile C19-ketone derivative
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