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(2E,6E)-farnesyl diphosphate + H2O
(+)-isoafricanol + diphosphate
(2E,6E)-farnesyl diphosphate + H2O
(+)-isoafricanol + diphosphate
-
-
-
-
?
(2E,6E)-farnesyl diphosphate + H2O
(+)-isoafricanol + diphosphate
-
the sesquiterpene alcohol (+)-isoafricanol is the main product (ca. 95%) plus traces of african-1-ene and african-2(6)-ene that are identified by GC/MS, (+)-isoafricanol i.e. (1aS,4aR,5R,7aS,7bR)-3,3,5,7b-tetramethyldecahydro-4aH-cyclopropa[e]azulen-4a-ol. Type I terpene cyclases ionise these achiral linear precursors by diphosphate abstraction, resulting in an allyl cation that undergoes multistep cyclisation cascades to a usually polycyclic terpene with several stereocentres. The cyclisation mechanism is extensively studied using isotopically labelled precursors. The enzyme follows a strict stereochemical course with respect to the fate of the geminal methyl groups C12 and C13, as observed for most terpene cyclases. Stereoselectively deuterated and 13C-labelled substrates reveal inversion of configuration at C1 during 1,11-cyclisation. Appropriate combinations of deuterium and 13C-labellings reveal two 1,2-hydride migrations including the stereochemical course for the second shift. No activity with geranyl diphosphate and geranylgeranyl diphosphate
-
-
?
(2E,6E)-farnesyl diphosphate + H2O
(+)-isoafricanol + diphosphate
-
-
-
-
?
(2E,6E)-farnesyl diphosphate + H2O
(+)-isoafricanol + diphosphate
-
the sesquiterpene alcohol (+)-isoafricanol is the main product (ca. 95%) plus traces of african-1-ene and african-2(6)-ene that are identified by GC/MS, (+)-isoafricanol i.e. (1aS,4aR,5R,7aS,7bR)-3,3,5,7b-tetramethyldecahydro-4aH-cyclopropa[e]azulen-4a-ol. Type I terpene cyclases ionise these achiral linear precursors by diphosphate abstraction, resulting in an allyl cation that undergoes multistep cyclisation cascades to a usually polycyclic terpene with several stereocentres. The cyclisation mechanism is extensively studied using isotopically labelled precursors. The enzyme follows a strict stereochemical course with respect to the fate of the geminal methyl groups C12 and C13, as observed for most terpene cyclases. Stereoselectively deuterated and 13C-labelled substrates reveal inversion of configuration at C1 during 1,11-cyclisation. Appropriate combinations of deuterium and 13C-labellings reveal two 1,2-hydride migrations including the stereochemical course for the second shift. No activity with geranyl diphosphate and geranylgeranyl diphosphate
-
-
?
(2E,6E)-farnesyl diphosphate + H2O
(+)-isoafricanol + diphosphate
(+)-isoafricanol i.e. (1aS,4aR,5R,7aS,7bR)-3,3,5,7b-tetramethyldecahydro-4aH-cyclopropa[e]azulen-4a-ol
-
-
?
(2E,6E)-farnesyl diphosphate + H2O
(+)-isoafricanol + diphosphate
(+)-isoafricanol i.e. (1aS,4aR,5R,7aS,7bR)-3,3,5,7b-tetramethyldecahydro-4aH-cyclopropa[e]azulen-4a-ol
-
-
?
(2E,6E)-farnesyl diphosphate + H2O
(+)-isoafricanol + diphosphate
(+)-isoafricanol i.e. (1aS,4aR,5R,7aS,7bR)-3,3,5,7b-tetramethyldecahydro-4aH-cyclopropa[e]azulen-4a-ol
-
-
?
(2E,6E)-farnesyl diphosphate + H2O
(+)-isoafricanol + diphosphate
-
(+)-isoafricanol i.e. (1aS,4aR,5R,7aS,7bR)-3,3,5,7b-tetramethyldecahydro-4aH-cyclopropa[e]azulen-4a-ol
-
-
?
(2E,6E)-farnesyl diphosphate + H2O
(+)-isoafricanol + diphosphate
-
(+)-isoafricanol i.e. (1aS,4aR,5R,7aS,7bR)-3,3,5,7b-tetramethyldecahydro-4aH-cyclopropa[e]azulen-4a-ol
-
-
?
(2E,6E)-farnesyl diphosphate + H2O
(+)-isoafricanol + diphosphate
(+)-isoafricanol i.e. (1aS,4aR,5R,7aS,7bR)-3,3,5,7b-tetramethyldecahydro-4aH-cyclopropa[e]azulen-4a-ol
-
-
?
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Riclea, R.; Citron, C.A.; Rinkel, J.; Dickschat, J.S.
Identification of isoafricanol and its terpene cyclase in Streptomyces violaceusniger using CLSA-NMR
Chem. Commun. (Camb.)
50
4228-4230
2014
Streptomyces violaceusniger (G2P5T1), Streptomyces violaceusniger T 4113 (G2P5T1)
brenda
Rabe, P.; Samborskyy, M.; Leadlay, P.F.; Dickschat, J.S.
Isoafricanol synthase from Streptomyces malaysiensis
Org. Biomol. Chem.
15
2353-2358
2017
Streptomyces malaysiensis, Streptomyces violaceusniger, Streptomyces rapamycinicus (A0A0A0NRS4), Streptomyces rapamycinicus NRRL 5491 (A0A0A0NRS4), Streptomyces violaceusniger T 4113, Streptomyces malaysiensis DSM 4137
brenda