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Literature summary extracted from

  • Little, D.B.; Croteau, R.B.
    Alteration of product formation by directed mutagenesis and truncation of the multiple-product sesquiterpene synthases delta-selinene synthase and gamma-humulene synthase (2002), Arch. Biochem. Biophys., 402, 120-135.
    View publication on PubMed

Cloned(Commentary)

EC Number Cloned (Comment) Organism
4.2.3.56 expressed in Escherichia coli BL21(DE3) cells Abies grandis
4.2.3.60 expression in Escherichia coli Abies grandis
4.2.3.71 expression in Escherichia coli Abies grandis
4.2.3.76 expression in Escherichia coli Abies grandis

Protein Variants

EC Number Protein Variants Comment Organism
4.2.3.56 D343A the mutation results in severely impaired activity for olefin production (estimated kcat reduction by more than 3000fold), the mutant produces 27.9% sativene from (2E,6E)-farnesyl diphosphate as the main product and only 12.9% gamma-humulene (the main product of the wild type enzyme) Abies grandis
4.2.3.56 D343E the mutant produces 34.4% sativene from (2E,6E)-farnesyl diphosphate as the main product and no gamma-humulene (the main product of the wild type enzyme), the mutant is capable of producing sesquiterpenols (61% nerolidol and 14% bisabolol, very similar to wild type distribution) at a rate comparable to that of olefin formation by the wild type enzyme Abies grandis
4.2.3.56 D488A the mutant produces 40% sativene from (2E,6E)-farnesyl diphosphate as the main product and no gamma-humulene (the main product of the wild type enzyme) Abies grandis
4.2.3.56 D488E the mutant produces 19.6% sativene from (2E,6E)-farnesyl diphosphate as the main product and only 6.0% gamma-humulene (the main product of the wild type enzyme), olefin synthase activity is reduced to 3% of wild type enzyme Abies grandis
4.2.3.56 D488N the mutant produces 21.7% sativene from (2E,6E)-farnesyl diphosphate as the main product and only 18.7% gamma-humulene (the main product of the wild type enzyme) Abies grandis
4.2.3.56 D570N the mutant produces 13.1% sativene from (2E,6E)-farnesyl diphosphate as the main product and 29.3% gamma-humulene (the main product of the wild type enzyme) Abies grandis
4.2.3.56 Y566F the mutant produces 42.6% gamma-humulene (the main product of the wild type enzyme) Abies grandis
4.2.3.60 D331A mutation results in main products 24.6% delta-amorphene, 12.9 beta-bisabolene, 22.0% germacrene A Abies grandis
4.2.3.60 D331E mutation results in main products 16.6% beta-bisabolene, 29.3% germacrene A, 9.3% alpha-bisabolene Abies grandis
4.2.3.60 D475A mutation results in main products 16.6% beta-bisabolene, 29.1% germacrene A, 8.8% alpha-bisabolene Abies grandis
4.2.3.60 D475E mutation results in main products 13.4% siberene, 27.4% amorphene, 9.1% beta-bisabolene, 10.9% germacrene A Abies grandis
4.2.3.60 D475N mutation results in main products 16.8% siberene, 34.7% amorphene, 8.2% beta-bisabolene, 6.8% germacrene A Abies grandis
4.2.3.60 D566N mutation results in main products 20.6% beta-bisabolene, 29.1% germacrene A, 8.4% alpha-bisabolene Abies grandis
4.2.3.60 H16A mutation results in main products 2.0% delta-selinene, 19.5% germacrene A, 33.7% germacrene C, 21.9% germacrene B Abies grandis
4.2.3.60 H17A mutation results in main products 1.5% delta-selinene, 19.8% germacrene A, 34.0% germacrene C, 21.8% germacrene B Abies grandis
4.2.3.60 additional information truncation at residue R11 results in main products 8.7% delta-selinene, 17.7% germacrene A, 21.8% germacrene C, 32.4% germacrene B. Truncation at residue H16 results in main products 1.8% delta-selinene, 17.0% germacrene A, 27.6% germacrene C, 19.7% germacrene B, 18.0% gamma-humulene. Truncation at residue W21 results in main products 23.4% beta-bisabolene, 24.4% germacrene A, 15.2% germacrene C, 4.7% germacrene B, 26.4% gamma-humulene Abies grandis
4.2.3.60 R11A mutation results in main products 2.5% delta-selinene, 18.2% germacrene A, 33.2% germacrene C, 26.5% germacrene B Abies grandis
4.2.3.60 R12A mutation results in main products 3.4% delta-selinene, 17.7% germacrene A, 35.8% germacrene C, 28.1% germacrene B Abies grandis
4.2.3.60 Y552F mutation results in main products 9.1% dleta-selinene, 17.0% germacrene A, 22.9% germacrene C, 33.4% germacrene B Abies grandis
4.2.3.71 D331A mutation results in main products 24.6% delta-amorphene, 12.9 beta-bisabolene, 22.0% germacrene A Abies grandis
4.2.3.71 D331E mutation results in main products 16.6% beta-bisabolene, 29.3% germacrene A, 9.3% alpha-bisabolene Abies grandis
4.2.3.71 D475A mutation results in main products 16.6% beta-bisabolene, 29.1% germacrene A, 8.8% alpha-bisabolene Abies grandis
4.2.3.71 D475E mutation results in main products 13.4% siberene, 27.4% amorphene, 9.1% beta-bisabolene, 10.9% germacrene A Abies grandis
4.2.3.71 D475N mutation results in main products 16.8% siberene, 34.7% amorphene, 8.2% beta-bisabolene, 6.8% germacrene A Abies grandis
4.2.3.71 D566N mutation results in main products 20.6% beta-bisabolene, 29.1% germacrene A, 8.4% alpha-bisabolene Abies grandis
4.2.3.71 H16A mutation results in main products 2.0% delta-selinene, 19.5% germacrene A, 33.7% germacrene C, 21.9% germacrene B Abies grandis
4.2.3.71 H17A mutation results in main products 1.5% delta-selinene, 19.8% germacrene A, 34.0% germacrene C, 21.8% germacrene B Abies grandis
4.2.3.71 additional information truncation at residue R11 results in main products 8.7% delta-selinene, 17.7% germacrene A, 21.8% germacrene C, 32.4% germacrene B. Truncation at residue H16 results in main products 1.8% delta-selinene, 17.0% germacrene A, 27.6% germacrene C, 19.7% germacrene B, 18.0% gamma-humulene. Truncation at residue W21 results in main products 23.4% beta-bisabolene, 24.4% germacrene A, 15.2% germacrene C, 4.7% germacrene B, 26.4% gamma-humulene Abies grandis
4.2.3.71 R11A mutation results in main products 2.5% delta-selinene, 18.2% germacrene A, 33.2% germacrene C, 26.5% germacrene B Abies grandis
4.2.3.71 R12A mutation results in main products 3.4% delta-selinene, 17.7% germacrene A, 35.8% germacrene C, 28.1% germacrene B Abies grandis
4.2.3.71 Y552F mutation results in main products 9.1% dleta-selinene, 17.0% germacrene A, 22.9% germacrene C, 33.4% germacrene B Abies grandis
4.2.3.76 D331A mutation results in main products 24.6% delta-amorphene, 12.9 beta-bisabolene, 22.0% germacrene A Abies grandis
4.2.3.76 D331E mutation results in main products 16.6% beta-bisabolene, 29.3% germacrene A, 9.3% alpha-bisabolene Abies grandis
4.2.3.76 D475A mutation results in main products 16.6% beta-bisabolene, 29.1% germacrene A, 8.8% alpha-bisabolene Abies grandis
4.2.3.76 D475E mutation results in main products 13.4% siberene, 27.4% amorphene, 9.1% beta-bisabolene, 10.9% germacrene A Abies grandis
4.2.3.76 D475N mutation results in main products 16.8% siberene, 34.7% amorphene, 8.2% beta-bisabolene, 6.8% germacrene A Abies grandis
4.2.3.76 D566N mutation results in main products 20.6% beta-bisabolene, 29.1% germacrene A, 8.4% alpha-bisabolene Abies grandis
4.2.3.76 H16A mutation results in main products 2.0% delta-selinene, 19.5% germacrene A, 33.7% germacrene C, 21.9% germacrene B Abies grandis
4.2.3.76 H17A mutation results in main products 1.5% delta-selinene, 19.8% germacrene A, 34.0% germacrene C, 21.8% germacrene B Abies grandis
4.2.3.76 additional information truncation at residue R11 results in main products 8.7% delta-selinene, 17.7% germacrene A, 21.8% germacrene C, 32.4% germacrene B. Truncation at residue H16 results in main products 1.8% delta-selinene, 17.0% germacrene A, 27.6% germacrene C, 19.7% germacrene B, 18.0% gamma-humulene. Truncation at residue W21 results in main products 23.4% beta-bisabolene, 24.4% germacrene A, 15.2% germacrene C, 4.7% germacrene B, 26.4% gamma-humulene Abies grandis
4.2.3.76 R11A mutation results in main products 2.5% delta-selinene, 18.2% germacrene A, 33.2% germacrene C, 26.5% germacrene B Abies grandis
4.2.3.76 R12A mutation results in main products 3.4% delta-selinene, 17.7% germacrene A, 35.8% germacrene C, 28.1% germacrene B Abies grandis
4.2.3.76 Y552F mutation results in main products 9.1% dleta-selinene, 17.0% germacrene A, 22.9% germacrene C, 33.4% germacrene B Abies grandis

Organism

EC Number Organism UniProt Comment Textmining
4.2.3.56 Abies grandis O64405 grand fir
-
4.2.3.60 Abies grandis O64404
-
-
4.2.3.71 Abies grandis O64404
-
-
4.2.3.76 Abies grandis O64404
-
-

Purification (Commentary)

EC Number Purification (Comment) Organism
4.2.3.56 hydroxyapatite column chromatography followed by gradient elution from an anion-exchange matrix Abies grandis
4.2.3.60 partial Abies grandis
4.2.3.71 partial Abies grandis
4.2.3.76 partial Abies grandis

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
4.2.3.56 (2E,6E)-farnesyl diphosphate
-
 Abies grandis gamma-humulene + diphosphate gamma-humulene is the main product (30.9% yield) of the wild type enzyme ?
4.2.3.56 additional information besides gamma-humulene (30.9% yield), gamma-humulene synthase produces 18.9% siberene, 11.4% longifolene, 7.4% beta-bisabolene, 4.3% sativene, 4.1% alpha-longipinene, 3.0% beta-farnesene, 2.6% alpha-ylangene, 2.1% beta-gurjunene, 2.0% gamma-bisabolene, 1.7% beta-longipinene, 1.3% alpha-bisaolene, 1.3% alpha-himachalene, 1.1% gamma-himachalene, 1.0% cyclosativene, 0.6% beta-ylangene, and 0.2% beta-cubebene Abies grandis ?
-
 ?
4.2.3.60 (2E,6E)-farnesyl diphosphate
-
 Abies grandis germacrene C + diphosphate main products are 12.3% delta-selinene, 17.2% germacrene A, 14.2% germacrene C, 33.2% germacrene B ?
4.2.3.71 (2E,6E)-farnesyl diphosphate
-
 Abies grandis germacrene B + diphosphate main products are 12.3% delta-selinene, 17.2% germacrene A, 14.2% germacrene C, 33.2% germacrene B ?
4.2.3.76 (2E,6E)-farnesyl diphosphate
-
 Abies grandis (+)-delta-selinene + diphosphate main products are 12.3% delta-selinene, 17.2% germacrene A, 14.2% germacrene C, 33.2% germacrene B ?

Synonyms

EC Number Synonyms Comment Organism
4.2.3.56 gamma-humulene synthase
-
 Abies grandis
4.2.3.56 gammaHS
-
 Abies grandis