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EC Tree
IUBMB Comments Initial cyclization probably gives biyclogermacrene in an enzyme bound form which is not released to the medium. The enzyme from Solidago canadensis also forms a small amount of (+)-gamma-gurjunene .
The enzyme appears in viruses and cellular organisms
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(2E,6E)-farnesyl diphosphate = (-)-alpha-gurjunene + diphosphate
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(2E,6E)-farnesyl-diphosphate diphosphate-lyase [(-)-alpha-gurjunene-forming]
Initial cyclization probably gives biyclogermacrene in an enzyme bound form which is not released to the medium. The enzyme from Solidago canadensis also forms a small amount of (+)-gamma-gurjunene [1].
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(2E,6E)-farnesyl diphosphate
(-)-alpha-gurjunene + diphosphate
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initial step is the formation of a germacrenyl cation after abstraction of the diphosphate group. Internal shifts of electron pairs lead to the patchoulenyl cation, which then undergoes a double 1,2-hydride shift. Rearrangement leads to the aromadendrenyl cation, which then undergoes a 1,2-hydride shift. Abstraction of a proton by the enzyme yields isoledene, which is reprotonated at the active site of the enzyme. At this junction two proton abstractions are possible, one leading to (-)-alpha-gurjunene and the other to (+)-gamma-gurjunene
product ratio 91% (-)-alpha-gurjunene and 9% (+)-gamma-gurjunene
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(2E,6E)-farnesyl diphosphate
alpha-gurjunene + diphosphate
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additional information
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no activity with geranyl diphosphate and geranylgeranyl diphosphate
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(2E,6E)-farnesyl diphosphate
alpha-gurjunene + diphosphate
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0.0055
(2E,6E)-farnesyl diphosphate
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pH 7.0, 30°C
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5.1
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calculated from amino acid sequence
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female flower
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highest expression in young leaves
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additional information
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the enzyme is absent in male flowers, phloem, xylem, bark, root, and 22-day-old seedlings
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MTSL4_MARPO
431
0
50271
Swiss-Prot
other Location (Reliability: 4 )
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60000
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1 * 60000, SDS-PAGE
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x * 70200, calculated from amino acid sequence
monomer
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1 * 60000, SDS-PAGE
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expressed in Escherichia coli BL21(DE3) cells
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enzyme expression in leaves is enhanced 61fold by 0.1 mM salicylic acid after 2 h
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enzyme expression is not affected by jasmonic acid treatment and physical wounding
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Schmidt, C.O.; Bouwmeester, H.J.; Buelow, N.; Koenig, W.A.
Isolation, characterization, and mechanistic studies of (-)-alpha-gurjunene synthase from Solidago canadensis
Arch. Biochem. Biophys.
364
167-177
1999
Solidago canadensis
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Hsieh, H.; Ma, L.; Wang, S.; Chu, F.
Cloning and expression of a sesquiterpene synthase gene from Taiwania cryptomerioides
Holzforschung
69
1041-1048
2015
Taiwania cryptomerioides
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