Detection of 1,2-hydride shifts in the formation of euph-7-ene by the squalene-tetrahymanol cyclase of Tetrahymena pyriformis.

@article{Giner2005DetectionO1,
  title={Detection of 1,2-hydride shifts in the formation of euph-7-ene by the squalene-tetrahymanol cyclase of Tetrahymena pyriformis.},
  author={Jos{\'e}-Luis Giner and Stefano Rocchetti and Serge J.M. Neunlist and Michel. Rohmer and Duilio Arigoni},
  journal={Chemical communications},
  year={2005},
  volume={24},
  pages={
          3089-91
        }
}
Incubation of samples of 2,3-dihydrosqualene, specifically labeled with deuterium at either carbon position 7 or 11, with an enzyme extract from Tetrahymena pyriformis, containing a squalene-tetrahymanol cyclase, provided specimens of euph-7-enes displaying deuterium patterns consistent with the biosynthetic operation of two consecutive 1,2-hydride shifts. 
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Enzymatic synthesis of cyclic triterpenes.
  • I. Abe
  • Chemistry
    Natural product reports
  • 2007
TLDR
Recent crystallographic and structure-based mutagenesis studies as well as utilization of chemically synthesized active-site probes have begun to reveal intimate structural details of the enzyme-templated cyclization reactions.
A Novel Soluble Squalene-Hopene Cyclase and Its Application in Efficient Synthesis of Hopene
TLDR
A novel SHC named OUC-SaSHC is found from Streptomyces albolongus ATCC 27414 with great potential for use as biocatalyst on scale-up production of hopene and improves the SHC-catalyzing enzyme synthesis ofHopene from laboratory level to application level.
Deciphering the evolutionary history of microbial cyclic triterpenoids.

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The cyclase of the protozoon Tetrahymena pyriformis, which normally converts squalene into the pentacyclic tetrahymanol, cyclized 2,3-dihydrosqualene into euph-7-ene with an unexpected tetracyclic…
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Cell-free systems from the protozoon Tetrahymena pyriformis and the bacterium Alicyclobacillus acidocaldarius normally convert squalene into pentacyclic triterpenes of the gammacerane and hopane…
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The absolute stereochemistry of cubenene and epicubenol from cultured cells of Heteroscyphus planus was determined as both (+)-isomers by 1H and 13C NMR spectroscopy, GLC using a chiral capillary…
Functional analysis of phenylalanine 365 in hopene synthase, a conserved amino acid in the families of squalene and oxidosqualene cyclases†
Two bicyclic products were accumulated by the mutant F365A, showing the amino acid residue is located close to the transient C-8 carbocation intermediate in the active site cavity; the mutants of…
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TLDR
The cyclization of hexaprenyl methyl ether is the first attempt of identification of these tricyclopolyprenol derivatives in living organisms.
Fern constituents: Polypodatetraenes, novel bicyclic triterpenoids, isolated from polypodiaceous and aspidiaceous plants
Stereochemical aspects of sesquiterpene biosynthesis
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