The enzyme is activated by Mg2+ . Similar to many other plant terpenoid synthases, this enzyme produces many products from a single substrate. The predominant product is the cyclic sesquiterpenoid alcohol, 8-epi-cedrol, with minor products including cedrol and the olefins alpha-cedrene, beta-cedrene, (E)-beta-farnesene and (E)-alpha-bisabolene .
reaction mechanism and cyclization of 8-epi-cedrol. Allylic carbocation formation, isomerization to nerolidyl diphosphate, and cyclization generate the monocyclic bisabolyl cation, a hydride shift is followed by two cyclizations to yield the cedryl cation, and the reaction is terminated by quenching the tricyclic cation with a hydroxide equivalent to form 8-epicedrol, overview
The enzyme is activated by Mg2+ [2]. Similar to many other plant terpenoid synthases, this enzyme produces many products from a single substrate. The predominant product is the cyclic sesquiterpenoid alcohol, 8-epi-cedrol, with minor products including cedrol and the olefins alpha-cedrene, beta-cedrene, (E)-beta-farnesene and (E)-alpha-bisabolene [1].
geranyl diphosphate is converted to monoterpenes by the recombinant enzyme at a rate of about 15% of that observed with farnesyl diphosphate as substrate
the native enzyme is specifically producing 8-epi-cedrol, but the enzyme recombinantly expressed in Escherichia coli also produces cedrol, with 8-epi-cedrol and cedrol in a 96:4 ratio, GC-MS product analysis, overview
Sesquiterpene cyclases or synthases catalyze the conversion of the isoprenoid intermediate farnesyl diphosphate to various sesquiterpene structural types
Sesquiterpene cyclases or synthases catalyze the conversion of the isoprenoid intermediate farnesyl diphosphate to various sesquiterpene structural types
product formation specificity, overview. Native epi-cedrol synthase is not active with geranylgeranyl diphosphate as substrate. The recombinant enzyme catalyzes the formation of both olefinic sesquiterpene, i.e. 57% alpha-cedrene, 13% beta-cedrene, 5% (E)-beta-farnesene , 1% alpha-acoradiene, 8% (E)-alpha-bisabolene, and 16% of three unknown olefins, but mainly oxygenates sesquiterpenes, 97% of total sesquiterpene generated, composed of 96% epi-cedrol and 4% cedrol, from farnesyl diphosphate, GC-MS product analysis, overview
product formation specificity, overview. Native epi-cedrol synthase is not active with geranylgeranyl diphosphate as substrate. The recombinant enzyme catalyzes the formation of both olefinic sesquiterpene, i.e. 57% alpha-cedrene, 13% beta-cedrene, 5% (E)-beta-farnesene , 1% alpha-acoradiene, 8% (E)-alpha-bisabolene, and 16% of three unknown olefins, but mainly oxygenates sesquiterpenes, 97% of total sesquiterpene generated, composed of 96% epi-cedrol and 4% cedrol, from farnesyl diphosphate, GC-MS product analysis, overview
Sesquiterpene cyclases or synthases catalyze the conversion of the isoprenoid intermediate farnesyl diphosphate to various sesquiterpene structural types
Sesquiterpene cyclases or synthases catalyze the conversion of the isoprenoid intermediate farnesyl diphosphate to various sesquiterpene structural types
functional expression in Saccharomyces cerevisiae, native mating type alpha yeast strain JBY574 and constructed strain EHY42, leading to production of sesquiterpenes in yeast. Expressing epi-cedrol synthase in the upc2-1 mutant CJ-2A actually decreases foreign sesquiterpene yields relative to wild-type strain. FPP is apparently less accessible to the epi-cedrol synthase in the upc2-1 mutant, overview. Mating type influences foreign sesquiterpene production, overview
homology-based cloning from a cDNA library, DNA and amino acid sequence determination and analysis, cloning and expression in Escherichia coli strains DH5alpha and BL21(DE3), respectively