Requires Mg2+. The enzyme from Pogostemon cablin gives 13% alpha-guaiene as well as 37% (-)-patchoulol (see EC 4.2.3.70), 13% delta-guaiene (see EC 4.2.3.93), and traces of at least ten other sesquiterpenoids . In Aquilaria crassna three clones of the enzyme gave about 80% delta-guaiene and 20% alpha-guaiene, with traces of alpha-humulene. A fourth clone gave 54% delta-guaiene and 45% alpha-guaiene .
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The enzyme appears in viruses and cellular organisms
Requires Mg2+. The enzyme from Pogostemon cablin gives 13% alpha-guaiene as well as 37% (-)-patchoulol (see EC 4.2.3.70), 13% delta-guaiene (see EC 4.2.3.93), and traces of at least ten other sesquiterpenoids [1]. In Aquilaria crassna three clones of the enzyme gave about 80% delta-guaiene and 20% alpha-guaiene, with traces of alpha-humulene. A fourth clone gave 54% delta-guaiene and 45% alpha-guaiene [2].
GC-MS libraries enable identification of the major products as alpha-guaiene (44%) and alpha-bulnesene (35%, also known as delta-guaiene). A number of minor products are also produced, putatively annotated as epiglobulol, gamma-gurjunene, and pogostol, that also exhibit the characteristic guaiene-type 5,7 bicyclic carbon skeleton of the peppery aroma compound rotundone. Substrate analysis of wild-type and mutant enzymes compared to selinene synthase, EC 4.2.3.86
GC-MS libraries enable identification of the major products as alpha-guaiene (44%) and alpha-bulnesene (35%, also known as delta-guaiene). A number of minor products are also produced, putatively annotated as epiglobulol, gamma-gurjunene, and pogostol, that also exhibit the characteristic guaiene-type 5,7 bicyclic carbon skeleton of the peppery aroma compound rotundone. Substrate analysis of wild-type and mutant enzymes compared to selinene synthase, EC 4.2.3.86
enzyme produces alpha-guaiene, a precursor of rotundone, proposed pathway for (-)-rotundone biosynthesis overview. Analysis of the cultivars Syrah, grown in the Iwaimura and Johnohira vineyards in Japan, reveals that the expression levels of the mevalonate pathway genes, Vixadtis vinifera terpene synthase gene (VvTPS24) and cyxadtochrome P450 gene (CYP71BE5) in the final step of (-)-rotundone biosynthesis are not significantly difxadferent between samples from the two vineyards during grape maturation. In contrast, the farnesyl diphosxadphate synthase gene (FPPS) expression level is conxadsiderably higher in the grape exocarp from the Johnoxadhira vineyard than in that from the Iwaimura vineyard. Relationship between alpha-guaiene and (-)-rotundone accumulation during grape maturation in the grape exocarp, overview
the T414 and V530 residues both contribute to the internal binding site of farnesyl diphosphate and are located on separate alpha-helices that contribute to the formation of the internal cavity comprising the FPP substrate-binding site. Molecular modelling of the two enzymes, selinene synthase (EC 4.2.3.86) and alpha-guayene synthase (EC 4.2.3.87) based on the TEAS template structure reveals that two of the varying amino acid positions are directly located in the active site, proximal to the location of FPP binding and subsequent catalysis, while the other four amino acid differences are located more peripherally, structure-function analysis
the T414 and V530 residues both contribute to the internal binding site of farnesyl diphosphate and are located on separate alpha-helices that contribute to the formation of the internal cavity comprising the FPP substrate-binding site. Molecular modelling of the two enzymes, selinene synthase (EC 4.2.3.86) and alpha-guayene synthase (EC 4.2.3.87) based on the TEAS template structure reveals that two of the varying amino acid positions are directly located in the active site, proximal to the location of FPP binding and subsequent catalysis, while the other four amino acid differences are located more peripherally, structure-function analysis
site-directed mutagenesis, the mutant shows a guaiene synthase activity that is almost completely compromised, with only 5% of the volatile products comprising alpha-guaiene, and alpha-bulnesene not detectable. Instead, the major products are predominantly the 6,6 bicyclic sesquiterpenes selina-4,11-diene (40%), alpha-selinene (23%), epi-alpha-selinene (12%), and a hydroxylated selinene (9%) with the same reported RI as intermedeo
gene VvGuaS, which is a polymorphic variant of the VvTPS24 gene, sequence comparisons and phylogenetic analysis, Agrobacterium-mediated transient expression of VvTPS24 cDNA in Nicotiana benthamiana leaves
Two key polymorphisms in a newly discovered allele of the Vitis vinifera TPS24 gene are responsible for the production of the rotundone precursor ?-guaiene