Isolated from the fungus Coprinus cinereus. The enzyme also forms (+)-delta-cadinene, beta-copaene, (+)-sativene and traces of several other sequiterpenoids [2-4]. It is found in many higher plants such as Magnolia grandiflora (Southern Magnolia) together with germacrene A . See EC 4.2.3.13, (+)-delta-cadinene synthase, EC 4.2.3.127, beta-copaene synthase, EC 4.2.3.129, (+)-sativene synthase, and EC 4.2.3.23, germacrene A synthase.
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The enzyme appears in viruses and cellular organisms
reaction mechanism, structure-function relationship, overview. The reaction mechanism for (E,E)-FPP cyclization by Cop4 involves the 1,10-cyclization of a cisoid neryl cation to form a (Z,E)-germacradienyl cation, which undergoes a 1,3-hydride shift to form an allylic carbocation that is either deprotonated to yield (-)-germacrene D, the major product of Cop4, or 1,6 cyclized to the bicyclic cadinyl cation
Isolated from the fungus Coprinus cinereus. The enzyme also forms (+)-delta-cadinene, beta-copaene, (+)-sativene and traces of several other sequiterpenoids [2-4]. It is found in many higher plants such as Magnolia grandiflora (Southern Magnolia) together with germacrene A [1]. See EC 4.2.3.13, (+)-delta-cadinene synthase, EC 4.2.3.127, beta-copaene synthase, EC 4.2.3.129, (+)-sativene synthase, and EC 4.2.3.23, germacrene A synthase.
Cop4 converts 30% of (E)-geraniol diphosphate into cyclic monoterpene products. Limonene is synthesized as the major cyclic monoterpene product. Limonene can be derived from either a cisoid, exo- or cisoid, endo-conformation of the initial geranyl cation of the initial geranyl cation. Exo-conformation yields (Z)-beta-ocimene and linalool, while the endoconformation would give (E)-beta-ocimene
enzyme CoTPS2 is multifunctional and a terpene synthase that catalyses the synthesis of three sesquiterpenes, beta-ylangene, beta-copaene, and beta-cubebene
Cop4 is a catalytically promiscuous enzyme that cyclizes (2E,6E)-farnesyl diphosphate into multiple products, including (-)-germacrene D and cubebol. Cop 4 produces several volatile sesquiterpene products, including delta-cadinene as the major product, when expressed in Escherichia coli
the dominant reaction products generated by Mg25 are beta-cubebene with 24.5%, alpha-muurolene with 19.3%, cf. EC 4.2.3.125, delta-cadinol with 18.6%, delta-elemene with 16.0%, tau-muurolene with 10.8%, and beta-elemene with 10.8%
the enzyme also forms beta-caryophyllene via (Z,E)-germacradienyl cation and (E,E)-humulyl cation intermediates. The product profile of the VvShirazTPS-Y2 reaction includes alpha- and beta-cubebene, alpha-copaene, isocaryophyllene, alpha-caryophyllene, (+)-delta-cadinene, cadina-1,4-diene, and caryophyllene oxide, overview. The major products are isocaryophyllene and beta-cubenene
enzyme CoTPS2 is multifunctional and a terpene synthase that catalyses the synthesis of three sesquiterpenes, beta-ylangene, beta-copaene, and beta-cubebene
Cop4 is a catalytically promiscuous enzyme that cyclizes (2E,6E)-farnesyl diphosphate into multiple products, including (-)-germacrene D and cubebol. Cop 4 produces several volatile sesquiterpene products, including delta-cadinene as the major product, when expressed in Escherichia coli
the dominant reaction products generated by Mg25 are beta-cubebene with 24.5%, alpha-muurolene with 19.3%, cf. EC 4.2.3.125, delta-cadinol with 18.6%, delta-elemene with 16.0%, tau-muurolene with 10.8%, and beta-elemene with 10.8%
required, enzyme CoTPS2 has the conserved aspartate-rich motif (DDXXD) and NSE/DTE motifs that chelate divalent metal ions, typically Mg2+, in the C-terminal domain
required, substitution of Mg2+ with Mn2+ as the divalent metal ion shifts the product profile of Cop4 to germacrene D, disfavoring subsequent ring closures that produce the cadinyl cation and its tricyclic descendents. Two consensus sequences - an aspartate rich DDXXD/E and a NSE/DTE motif - located at the entrance of the active site coordinate a trinuclear Mg2+ cluster that ligands the diphosphate moiety of the isoprenoid substrate, positions the isoprenyl chain in the binding pocket and triggers closure of the active site along with diphosphate cleavage to generate an initial transoid, allylic carbocation
substitution of Mg2+ with Mn2+ as the divalent metal ion shifts the product profile of Cop4 to germacrene D, disfavoring subsequent ring closures that produce the cadinyl cation and its tricyclic descendents
increasing the reaction temperature to 37°C decreases the fidelity of Cop4. At this temperature Cop4 generates a relative larger fraction of products beta-cubebene, sativene, delta-cadinene and beta-copaene, that are derived from a cadinyl cation intermediate
changing the pH of the reaction drastically alters the fidelity of Cop4 and makes it a highly selective enzyme. Increasing the reaction temperature to 37°C decreases the fidelity of Cop4. At this temperature Cop4 generates a relative larger fraction of products beta-cubebene, sativene, delta-cadinene and beta-copaene, that are derived from a cadinyl cation intermediate. The histidine side chain in the Cop4 loop, in particular, has a strong impact on the net charge of the loop at different pH values
the enzyme expression increases from undeveloped small flowers to mature green flowers, is absent in mature yellow flowers, but very high in flower buds
in orange tissues, the sesquiterpene profile is qualitatively rich. Overall, up to 25 sesquiterpenes are identified in total, overview. Small amounts of beta-caryophyllene are detected in all samples, while alpha-copaene, beta-elemene, alpha-humulene, and alpha-selinene are emitted by all tissues except young leaves. Beside this, each tissue shows a characteristic sesquiterpene emission profile. Major sesquiterpenes emitted by adult leaves are beta-elemene and beta-caryophyllene, while flowers emitt nerolidol, absent from most tissues analyzed. In fruit tissues, valencene emission contributes greatly to total emitted volatiles, in much more extent in peel than in pulp
the terpene synthase Mg25 belongs to the angiosperm sesquiterpene synthase subclass TPS-a. The structural diversity observed in the three Magnolia terpene synthase genes have occurred either by a rapid loss of introns from a common ancestor TPS gene or by a gain of introns into an intron-deficient progenote TPS gene
the enzyme belongs to the terpene sythase superfamily, subfamily TPS-a. The arginine-tryptophan motif, R(R)X8W, present at the N terminus of most mono-TPS and in some sesqui-TPS and di-TPS, is found in CoTPS2. CoTPS2 does not contain a plastid Tp sequence
the farnesyl cation can undergo either 1,10- or 1,11-cyclization, giving rise to either an (E,E)-germacradienyl cation or an (E,E)-humulyl cation, respectively
the enzyme belongs to the sesquiterpene synthases that are responsible for the cyclization of farnesyl diphosphate into a myriad of structurally diverse compounds with various biological activities
in sweet orange tissues sesquiterpene profile is qualitatively rich. Overall, up to 25 sesquiterpenes are identified in total. Enzyme CsSesquiTPS1 catalyzes formation of a 62:38% mixture of (Z)-beta-cubebene and alpha-copaene
recombinant CoTPS2 catalysed the synthesis of three compounds, beta-ylangene, beta-copaene, and beta-cubebene, from farnesyl diphosphate. CoTPS2 is a multifunctional beta-ylangene/beta-copaene/beta-cubebene synthase capable of producing three sesquiterpenes, beta-ylangene, beta-copaene, and beta-cubebene. The enzyme is part of the biosynthesis of volatile organic compounds (VOCs) in flowers. Floral scents are a key factor in plant-insect interactions and are vital for successful pollination. The scented flowers of Cananga odorata var. fruticosa are analysed by GC-MS and a total of 49 VOCs are identified at four different stages of flower development. The bulk of these VOCs are terpenes, mainly sesquiterpenes. Enzyme CoTPS2 is a multifunctional terpene synthase that catalyses the synthesis of three sesquiterpenes, beta-ylangene, beta-copaene, and beta-cubebene
directed mutations of the H-alpha1 loop have a marked effect on the product profile Cop4, loop mutations in Cop4 also implicate specific residues responsible for the pH sensitivity of the enzyme. In vivo analysis of sesquiterpene product profiles of H-alpha1 loop mutants, overview. Mutation of K233, presumed to interact with the second Asp92 in the DDXXD motif of Cop4, does not significantly change the overall product promiscuity of Cop4, though beta-cubebene, with 27% of total sesquiterpene products, does become the major product
structural modeling, structure-function relationship, overview. Changing the pH of the reaction drastically alters the fidelity of Cop4 and makes it a highly selective enzyme
two terpenes dominate the plant sesquiterpene profile, with beta-cubebene accounting for 31.3% of the total and beta-elemene for 25.3%. The enzyme contains the conserved Asp-rich domain, DDXXD, that coordinates substrate binding via the formation of divalent cation salt bridges
structure comparison, homology structural modeling of Cop enzymes, overview. Cop4 has a large active site cavity that undergoes substantial conformational change in the model upon ligand binding
site-directed mutagenesis, the mutation converts Cop4 into a much more selective enzyme that produces (-)-germacrene D as the major cyclization product with 50% of total sesquiterpenes products. The mutant makes beta-ylangene, which is a diastereomer of beta-copaene and not synthesized by wild-type Cop4
site-directed mutagenesis, mutation of K233, interacting with the second Asp92 in the DDXXD motif of Cop4, does not significantly change the overall product promiscuity of Cop4, though beta-cubebene 4 does become the major product
site-directed mutagenesis, the mutant shows a altered product profile compared to the wild-type enzyme with a slight reduction in beta-cubebene synthesis. The mutant does no longer show production of cubebol and has reduced (-)-germacrene D synthesis activity compared to the wild-type enzyme, synthesis of beta-cubebene, beta-copaene, delta-cadinene, and alpha-cubebene
site-directed mutagenesis, no production of beta-cubebene, the mutation converts Cop4 into a much more selective enzyme that produces (-)-germacrene D as the major cyclization product with 50% of total sesquiterpenes products. The mutant makes beta-ylangene, which is a diastereomer of beta-copaene and not synthesized by wild-type Cop4
site-directed mutagenesis, the mutant shows a altered product profile compared to the wild-type enzyme with an increase in beta-cubebene synthesis. The mutant does no longer show production of cubebol and (-)-germacrene D compared to the wild-type enzyme
directed mutations of the H-alpha1 loop have a marked effect on the product profile Cop4, loop mutations in Cop4 also implicate specific residues responsible for the pH sensitivity of the enzyme. H-alpha1 loop swap between Cop4 and Cop6 shifts Cop4 to a germacrene D synthase
gene CsSesquiTPS1, DNA and amino acid sequence determination and analysis, sequence comparisons and phylogenetic analysis, the enzyme encoded by CsSesquiTPS1 produces a 62:38% mixture of (Z)-beta-cubebene and alpha-copaene
gene Mg25, DNA and amino acid sequence determination and analysis, Mg25 has one single intron located near the 5' terminus of the gene, expression analysis and phylogenetic analysis
gene TPS2, sequence comparisons and phylogenetic analysis and tree, quantitative real-time PCR enzyme expression analysis, recombinant expression of His-tagged enzyme in Escherichia coli strain BL21(DE3)pLysS, transient and functional recombinant expression of YFP-tagged enzyme CoTPS2 in transgenic Nicotiana benthamiana leaves in cytosol under control of CaMV 35S promoter via Agrobacterium tumefaciens-mediated transfection method
The floral transcriptome of ylang ylang (Cananga odorata var. fruticosa) uncovers biosynthetic pathways for volatile organic compounds and a multifunctional and novel sesquiterpene synthase