EC Number   |
Substrates |
Organism |
Products |
Reversibility |
|---|
   4.2.3.9 | (2E,6E)-farnesyl diphosphate |
- |
Nicotiana tabacum |
(+)-5-epi-aristolochene + diphosphate |
- |
? |
| 4.2.3.9 | (2E,6E)-farnesyl diphosphate |
- |
Penicillium roqueforti |
(+)-5-epi-aristolochene + diphosphate |
- |
? |
| 4.2.3.9 | (2E,6E)-farnesyl diphosphate |
- |
Penicillium roqueforti |
(+)-5-epi-aristolochene + diphosphate |
the steric bulk of residue 92 is central in binding of farnesyl diphosphate to the active site of aristolochene synthase in a quasi-cyclic conformation, thereby facilitating attack of C1 by the C10-C11 double bond to produce the cis-fused decalin S-germacrene A. Reduction of the size of the side chain of residue 92 leads to the production of the alicyclic sesquiterpenes (E)-beta- and (E,E)-alpha-farnesene. The relative amounts of linear products formed depend linearly on the size of the residues at position 92 |
? |
| 4.2.3.9 | (2E,6E)-farnesyl diphosphate |
- |
Penicillium roqueforti |
(+)-aristolochene + diphosphate |
- |
? |
| 4.2.3.9 | (2E,6E)-farnesyl diphosphate |
- |
Penicillium roqueforti |
(+)-aristolochene + diphosphate |
major product (92%) |
? |
| 4.2.3.9 | (2E,6E)-farnesyl diphosphate |
- |
Nicotiana tabacum |
(+)-5-epiaristolochene + diphosphate |
in addition to the major products (+)-5-epiaristolochene (78.9%), its DELTA1(10) isomer (-)-4-epieremophilene (6.2%), and (R)-germacrene A (3.7%), incubations of (2Z,6E)-farnesyl diphosphate with the enzyme lead to 22 additional sesquiterpenes (11% of total products), among the identified minor products are (-)-R-cedrene, an isomer of (-)-prezizaene and an acoradiene (together accounting for 2.5% of the total hydrocarbon fraction) |
? |
| 4.2.3.9 | (2E,6E)-farnesyl diphosphate |
- |
Aspergillus terreus |
aristolochene + diphosphate |
- |
? |
| 4.2.3.9 | (2E,6E)-farnesyl diphosphate |
- |
Penicillium roqueforti |
aristolochene + diphosphate |
products are 91.5% aristolochene, 7.5% germacrene A, 1% valencene |
? |
| 4.2.3.9 | (2E,6E)-farnesyl diphosphate |
reaction proceeds via germacrene A and eudesmane cation. The amount of germacrene A generated by mutant enzymes serves as a measure of the stabilization of eudesmane cation |
Penicillium roqueforti |
aristolochene + diphosphate |
wild-type, about 8% of germacrene A as by-product. His-tagged wild-type, about 4% of germacrene A |
? |
| 4.2.3.9 | (2Z,6E)-farnesyl diphosphate |
- |
Nicotiana tabacum |
(+)-2-epiprezizaene + (-)-alpha-cedrene + (-)-beta-curcumene + alpha-acoradiene + 4-epi-alpha-acoradiene + alpha-bisabolol + epi-alpha-bisabolol + nerolidol + (2Z,6E)-farnesol + diphosphate |
(+)-2-epiprezizaene (44% yield), (-)-alpha-cedrene (21.5% yield), (-)-beta-curcumene (15.5% yield), alpha-acoradiene (3.9% yield), 4-epi-alpha-acoradiene (1.3% yield), alpha-bisabolol (1.8% yield), epi-alpha-bisabolol (1.8% yield), nerolidol (3.6% yield), (2Z,6E)-farnesol (6.7% yield) |
? |
