The synthesis of (S)-β-macrocarpene from (2E,6E)-farnesyl diphosphate proceeds in two steps. The first step is the cyclization to (S)-β-bisabolene. The second step is the isomerization to (S)-β-macrocarpene (cf. EC 5.5.1.17, (S)-β-macrocarpene synthase). The enzyme requires Mg2+ or Mn2+ for activity.
The enzyme appears in viruses and cellular organisms
The synthesis of (S)-beta-macrocarpene from (2E,6E)-farnesyl diphosphate proceeds in two steps. The first step is the cyclization to (S)-beta-bisabolene. The second steps is the isomerization to (S)-beta-macrocarpene (c.f. EC 5.5.1.a, (S)-beta-macrocarpene synthase). The enzyme requires Mg2+ or Mn2+ for activity.
The synthesis of (S)-beta-macrocarpene from (2E,6E)-farnesyl diphosphate proceeds in two steps. The first step is the cyclization to (S)-beta-bisabolene. The second step is the isomerization to (S)-beta-macrocarpene (cf. EC 5.5.1.17, (S)-beta-macrocarpene synthase). The enzyme requires Mg2+ or Mn2+ for activity.
Substrates: - Products: The synthesis of (S)-beta-macrocarpene from (2E,6E)-farnesyl diphosphate proceeds in two steps. The first step is the cyclization to (S)-beta-bisabolene. The second step is the isomerization to (S)-beta-macrocarpene ((S)-beta-macrocarpene synthase). Product is identified by GC-MS
Substrates: - Products: The synthesis of (S)-beta-macrocarpene from (2E,6E)-farnesyl diphosphate proceeds in two steps. The first step is the cyclization to (S)-beta-bisabolene. The second step is the isomerization to (S)-beta-macrocarpene ((S)-beta-macrocarpene synthase). Product is identified by GC-MS
Substrates: no activity with geranylgeranyl diphosphate. TPS6 accepts the monoterpene precursor geranyl diphosphate but the monoterpene products are produced at a lower velocity Products: -
Substrates: no activity with geranylgeranyl diphosphate. TPS6 accepts the monoterpene precursor geranyl diphosphate but the monoterpene products are produced at a lower velocity Products: -
Substrates: no activity with geranylgeranyl diphosphate. TPS6 accepts the monoterpene precursor geranyl diphosphate but the monoterpene products are produced at a lower velocity Products: -
TPS6 requires a divalent metal ion, with Mg2+ and Mn2+ being effective, optimum activity with 5 mM Mg2+ and 5 mM Mn2+. Although the Km for Mn2+ is significantly lower than for Mg2+, the enzyme is more likely to operate with a Mg2+ cofactor in planta, because the concentration of Mg2+ in plant cells is about 2 orders of magnitudes higher than Mn2+. In the presence of Mn2+, the product spectrum of TPS6 is shifted toward an increased production of (S)-beta bisabolene and a decreased production of (S)-beta-macrocarpene. KM-value for Mg2+ measured with 0.01 mM farnesyl diphosphate: 0.131 mM
TPS6 requires a divalent metal ion, with Mg2+ and Mn2+ being effective, optimum activity with 5 mM Mg2+ and 5 mM Mn2+. Although the Km for Mn2+ is significantly lower than for Mg2+, the enzyme is more likely to operate with a Mg2+ cofactor in planta, because the concentration of Mg2+ in plant cells is about 2 orders of magnitudes higher than Mn2+. In the presence of Mn2+, the product spectrum of TPS6 is shifted toward an increased production of (S)-beta bisabolene and a decreased production of (S)-beta-macrocarpene. KM-value for Mn2+ measured with 0.01 mM farnesyl diphosphate: 0.0234 mM
half-maximal activity at pH 6.2 and at pH 8.6, in presence of 5 mM Mg2+. Within a pH range from 5.0 to 8.0, the major product is (S)-beta-macrocarpene, but higher pH values favor the formation of (S)-beta-bisabolene
mutation reduces the production of (S)-beta-macrocarpene to trace amounts, the enzyme forms (S)-beta-bisabolene almost exclusively, the overall activity of the mutated enzyme is dramatically reduced
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CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
cloning from wood shavings from the interface of heartwood and sapwood from mature sandalwood trees, DNA and amino acid sequence determination and analysis, sequence comparisons and phylogenetic analysis, semi-quantitative real-time enzyme expression analysis, and transcriptome screening, recombinant expression of N-terminally His6-tagged enzyme in Escherichia coli strain Rosetta 2 (DE3)
Protonation of a neutral (S)-beta-bisabolene intermediate is involved in (S)-beta-macrocarpene formation by the maize sesquiterpene synthases TPS6 and TPS11
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