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Literature summary extracted from

  • Drew, D.P.; Andersen, T.B.; Sweetman, C.; M?ller, B.L.; Ford, C.; Simonsen, H.T.
    Two key polymorphisms in a newly discovered allele of the Vitis vinifera TPS24 gene are responsible for the production of the rotundone precursor ?-guaiene (2016), J. Exp. Bot., 67, 799-808 .
    View publication on PubMedView publication on EuropePMC

Cloned(Commentary)

EC Number Cloned (Comment) Organism
4.2.3.86 construction of the synthetic terpene synthase construct from the sequence of alpga-guaiene synthase (EC 4.2.3.87), sequence comparisons and phylogenetic analysis, the recombinant enzyme is transiently expressed in Nicotiana benthamiana leaves and produces mainly alpha-guaiene and alpha-bulnesene, and also lower amounts of alpha-copaene, alpha-gurjunene, gamm-gurlunene, epiglobulol, epi-?alpha-selinene, and pogostol. Selina-4(14),11-diene, alpha-selinene, delta-cadinene, and intermedeol are not found Vitis vinifera
4.2.3.87 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 Vitis vinifera

Protein Variants

EC Number Protein Variants Comment Organism
4.2.3.87 additional information the two polymorphisms within the active site of VvGuaS compared to VvPNSeInt (EC 4.2.3.86) correspond to T414S and V530M substitutions Vitis vinifera
4.2.3.87 T414S site-directed mutagenesis, the mutant shows altered substrate specificity compared to the wild-type enzyme Vitis vinifera
4.2.3.87 T414S/V530M 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 Vitis vinifera
4.2.3.87 V530M site-directed mutagenesis, the mutant shows altered substrate specificity compared to the wild-type enzyme Vitis vinifera

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
4.2.3.86 (2E,6E)-farnesyl diphosphate Vitis vinifera
-
 alpha-guaiene + diphosphate
-
 ?
4.2.3.87 (2E,6E)-farnesyl diphosphate Vitis vinifera
-
 alpha-guaiene + diphosphate
-
 ?

Organism

EC Number Organism UniProt Comment Textmining
4.2.3.86 Vitis vinifera AM459143 cv. Shiraz, grown in the Nuriootpa Research vineyard, Barossa Valley, South Australia, and harvested at various times of the 2013 season
-
4.2.3.87 Vitis vinifera E0CSJ0 cv. Shiraz, grown in the Nuriootpa Research vineyard, Barossa Valley, South Australia, and harvested at various times of the 2013 season
-

Source Tissue

EC Number Source Tissue Comment Organism Textmining
4.2.3.86 fruit
-
 Vitis vinifera
-
4.2.3.87 berry
-
 Vitis vinifera
-
4.2.3.87 fruit
-
 Vitis vinifera
-

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
4.2.3.86 (2E,6E)-farnesyl diphosphate
-
 Vitis vinifera alpha-guaiene + diphosphate
-
 ?
4.2.3.86 additional information substrate analysis of wild-type and mutant enzymes compared to alpha-guaiene synthase, EC 4.2.3.87 Vitis vinifera ?
-
 ?
4.2.3.87 (2E,6E)-farnesyl diphosphate
-
 Vitis vinifera alpha-guaiene + diphosphate
-
 ?
4.2.3.87 additional information 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 Vitis vinifera ?
-
 ?

Synonyms

EC Number Synonyms Comment Organism
4.2.3.86 selinene synthase
-
 Vitis vinifera
4.2.3.86 VvPNSeInt
-
 Vitis vinifera
4.2.3.87 TPS24
-
 Vitis vinifera
4.2.3.87 VIT_19s0014g02590
-
 Vitis vinifera
4.2.3.87 VvGuaS
-
 Vitis vinifera
4.2.3.87 VvTPS24
-
 Vitis vinifera

General Information

EC Number General Information Comment Organism
4.2.3.86 additional information 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 S414 and M530 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 Vitis vinifera
4.2.3.86 physiological function the enzyme produces alpha-guaiene, a precursor of rotundone Vitis vinifera
4.2.3.87 additional information 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 Vitis vinifera
4.2.3.87 physiological function the enzyme produces alpha-guaiene, a precursor of rotundone Vitis vinifera