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
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General Information
General Information on EC 1.14.14.58 - trimethyltridecatetraene synthase
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evolution
malfunction
metabolism
physiological function
CYP705A1 is a member of the Brassicaceae-specific CYP705 family
evolution
B6ST66, B8A110
the DMNT biosynthetic pathway and both (DMNT and TMTT) monooxygenases are distinct from those previously characterized for (E)-4,8-dimethyl-1,3,7-nonatriene, DMNT, and (E,E)-4,8,12-trimethyltrideca-1,3,7,11-tetraene, TMTT, synthesis in Arabidopsis thaliana, suggesting independent evolution of these enzymatic activities. The amino acid identity between the maize and Arabidopsis enzymes is below 30%
CYP82G1 gene knockout plants do not produce (E,E)-4,8,12-trimethyltrideca-1,3,7,11-tetraene and their phenotype is complemented by the constitutive expression of CYP82G1
malfunction
the null mutant cyp82g1-1 is not impaired in root-specific DMNT biosynthesis, indicating that enzyme Cyp82g1 is not involved in the formation of DMNT in Arabidopsis thaliana roots
enzyme CYP705A1 is involved in DMNT biosynthesis in Arabidopsis thaliana roots. The formation of (E)-4,8-dimethyl-1,3,7-nonatriene, DMNT, and (E,E)-4,8,12-trimethyl-1,3,7,11-tridecatetraene, TMTT, in leaf or flower tissues usually occurs by the oxidative breakdown of (E)-nerolidol or (E,E)-geranyl linalool. Arabidiol Is the precursor in DMNT biosynthesis in Arabidopsis thaliana roots, it can be degraded by CYP705A1 to a C19 ketone product (14-apo-arabidiol). Role of the DMNT biosynthetic pathway in resistance against Pythium irregulare
metabolism
B6ST66, B8A110
the C11 homoterpene (E)-4,8-dimethyl-1,3,7-nonatriene (DMNT) is formed by the oxidative degradation of (E)-nerolidol. (E,E)-4,8,12-Trimethyltrideca-1,3,7,11-tetraene (TMTT) is produced via oxidative degradation of (E,E)-geranyllinalool. The first step of both pathways, the formation of the tertiary terpene alcohols (E,E)-geranyllinalool and (E)-nerolidol, is catalyzed by the terpene synthase, TPS2, whereas the subsequent oxidative degradation to DMNT and TMTT is catalyzed by two specific P450 monooxygenases, CYP92C5 and CYP92C6. Pathway mapping of 26 parent lines of US-NAM population for pathways and enzymes contributing to volatile terpene biosynthesis in maize leaves. TPS2 is the regulatory key enzyme
enzyme CYP82G1 produces (3E)-4,8-dimethylnona-1,3,7-triene, DMNT, and (E,E)-4,8,12-trimethyltrideca-1,3,7,11-tetraene, TMTT, in vitro but functions as a TMTT synthase in planta because of the presence of (E,E)-geranyllinalool but not of (E)-nerolidol in Arabidopsis thaliana leaves
physiological function
B6ST66, B8A110
gene disruption of CYP92C5 results in loss of (3E)-4,8-dimethylnona-1,3,7-triene production and reduced levels of (3E,7E)-4,8,12-trimethyltrideca-1,3,7,11-tetraene after simulated herbivory. In planta (3E)-4,8-dimethylnona-1,3,7-triene is primarily produced by isoform CYP92C5, whereas the majority of (3E,7E)-4,8,12-trimethyltrideca-1,3,7,11-tetraene is produced by cytochrome P450 monooxygenase, CYP92C6
physiological function
while Arabidopsis thaliana and other angiosperms are known to produce the homoterpene (E)-4,8-dimethyl-1,3,7-nonatriene, DMNT, or its C16-analogue (E,E)-4,8,12-trimethyl-1,3,7,11-tridecatetraene, TMTT, by the breakdown of sesquiterpene and diterpene tertiary alcohols in aboveground tissues, Arabidopsis thaliana roots biosynthesize DMNT by the degradation of the C30 triterpene diol, arabidiol. The reaction is catalyzed by the Brassicaceae-specific cytochrome P450 monooxygenase CYP705A1. In volatile terpene biosynthesis, irregular homo/norterpenes can arise from different biosynthetic routes in a tissue-specific manner. DMNT negatively affects pathogen Pythium irregulare oospore germination and growth
physiological function
B6ST66, B8A110
while enzyme CYP92C5 converts (E)-nerolidol and (E,E)-geranyllinalool to (3E)-4,8-dimethyl-1,3,7,-nonatriene (DMNT) and (E,E)-4,8,12-trimethyltrideca-1,3,7,11-tetraene, respectively, enzyme CYP92C6 only converts (E,E)-geranyllinalool to (E,E)-4,8,12-trimethyltrideca-1,3,7,11-tetraene, TMTT. (E)-4,8-Dimethyl-1,3,7-nonatriene, DMNT, and (E,E)-4,8,12-trimethyltrideca-1,3,7,11-tetraene, TMTT, are volatile homoterpenes. Many such volatiles are assigned functions in the defense against pathogens like lepidopteran larvae, aphids, fungi,and bacteria. Maize volatiles released after herbivore damage display high levels of quantitative and qualitative variation. In planta, DMNT is primarily produced by CYP92C5, whereas the majority of TMTT is produced by a related cytochrome P450 monooxygenase, CYP92C6, which is specific for the conversion of (E,E)-geranyllinalool to TMTT
physiological function
B6ST66, B8A110
while enzyme CYP92C5 converts (E)-nerolidol and (E,E)-geranyllinalool to DMNT and (E,E)-4,8,12-trimethyltrideca-1,3,7,11-tetraene, respectively, enzyme CYP92C6 only converts (E,E)-geranyllinalool to (E,E)-4,8,12-trimethyltrideca-1,3,7,11-tetraene, TMTT. (E)-4,8-Dimethyl-1,3,7-nonatriene, DMNT, and (E,E)-4,8,12-trimethyltrideca-1,3,7,11-tetraene, TMTT, are volatile homoterpenes. Many such volatiles are assigned functions in the defense against pathogens like lepidopteran larvae, aphids, fungi,and bacteria. Maize volatiles released after herbivore damage display high levels of quantitative and qualitative variation. In planta, DMNT is primarily produced by CYP92C5, whereas the majority of TMTT is produced by a related cytochrome P450 monooxygenase, CYP92C6, which is specific for the conversion of (E,E)-geranyllinalool to TMTT