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Literature summary for 4.2.3.118 extracted from

  • Koeksal, M.; Chou, W.K.; Cane, D.E.; Christianson, D.W.
    Unexpected reactivity of 2-fluorolinalyl diphosphate in the active site of crystalline 2-methylisoborneol synthase (2013), Biochemistry, 52, 5247-5255.
    View publication on PubMedView publication on EuropePMC

Crystallization (Commentary)

Crystallization (Comment) Organism
in unliganded state and in complex with two Mg2+ ions and 2-fluoroneryl diphosphate at 1.85 and 2.00 A resolution, respectively. Cocrystallization with the fluorinated analogue of the tertiary allylic diphosphate intermediate, 2-fluorolinalyl diphosphate yields the crystal structure of the complex with the primary allylic diphosphate, 2-fluoroneryl diphosphate. The crystalline enzyme active site remains partially open, presumably due to the binding of only two Mg2+ ions Streptomyces coelicolor

Metals/Ions

Metals/Ions Comment Organism Structure
Mg2+ three Mg2+ ions are presumed to be required for the cyclization reaction Streptomyces coelicolor

Organism

Organism UniProt Comment Textmining
Streptomyces coelicolor Q9F1Y6
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Streptomyces coelicolor A3(2) Q9F1Y6
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Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
2-fluorolinalyl diphosphate + H2O
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Streptomyces coelicolor (1R)-(+)-camphor + HF + diphosphate single cyclic product, obtained via the (4R)-alpha-2-fluoroterpinyl carbocation intermediate. The initially generated 2-fluoroisoborneol cyclization product is unstable and undergoes elimination of hydrogen fluoride to yield (1R)-(+)-camphor ?
2-fluorolinalyl diphosphate + H2O
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Streptomyces coelicolor A3(2) (1R)-(+)-camphor + HF + diphosphate single cyclic product, obtained via the (4R)-alpha-2-fluoroterpinyl carbocation intermediate. The initially generated 2-fluoroisoborneol cyclization product is unstable and undergoes elimination of hydrogen fluoride to yield (1R)-(+)-camphor ?
2-methyllinalyl diphosphate + H2O natural intermediate of the cyclization reaction Streptomyces coelicolor 2-methylisoborneol + diphosphate
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?
2-methyllinalyl diphosphate + H2O natural intermediate of the cyclization reaction Streptomyces coelicolor A3(2) 2-methylisoborneol + diphosphate
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?