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Literature summary for 4.2.3.87 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
Search for more literature for 4.2.3.87

Cloned(Commentary)

Cloned (Comment) Organism
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

Protein Variants Comment Organism
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
T414S site-directed mutagenesis, the mutant shows altered substrate specificity compared to the wild-type enzyme Vitis vinifera
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
V530M site-directed mutagenesis, the mutant shows altered substrate specificity compared to the wild-type enzyme Vitis vinifera

Natural Substrates/ Products (Substrates)

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

Organism

Organism UniProt Comment Textmining
Vitis vinifera E0CSJ0 cv. Shiraz, grown in the Nuriootpa Research vineyard, Barossa Valley, South Australia, and harvested at various times of the 2013 season
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Source Tissue

Source Tissue Comment Organism Textmining
berry
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 Vitis vinifera
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fruit
-
 Vitis vinifera
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Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
(2E,6E)-farnesyl diphosphate
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 Vitis vinifera alpha-guaiene + diphosphate
-
 ?
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 ?
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 ?

Synonyms

Synonyms Comment Organism
TPS24
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 Vitis vinifera
VIT_19s0014g02590
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 Vitis vinifera
VvGuaS
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 Vitis vinifera
VvTPS24
-
 Vitis vinifera

General Information

General Information Comment Organism
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
physiological function the enzyme produces alpha-guaiene, a precursor of rotundone Vitis vinifera