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

  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},
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. 
Enzymatic synthesis of cyclic triterpenes.
  • I. Abe
  • Chemistry
    Natural product reports
  • 2007
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
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.


Enyzmatic cyclization of 2,3-dihydrosqualene into euph-7-ene by a cell-free system from the protozoon Tetrahymena pyriformis
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
Biosynthesis of terpenes and steroids. Part IV. Specific hydride shifts in the biosynthesis of lanosterol and β-amyrin
The hydride shifts accompanying 2,3-epoxysqualene cyclisation to lanosterol in yeast and to β-amyrin in peas have been checked using 2,3-epoxy[11,14-3H2]squalene. The results support the
Stereospecific synthesis of squalenoid epoxide vinyl ethers as inhibitors of 2,3-oxidosqualene cyclase
The stereospecific synthesis of squalenoid epoxide vinyl ethers with an isopentyloxy group is described. The synthesis involves the preparation of the C22 squalenoid aldehyde bromohydrin (15) by a
Enzymic cyclization of 2,3-dihydrosqualene and squalene 2,3-epoxide by squalene cyclases: from pentacyclic to tetracyclic triterpenes
Cell-free systems from the protozoon Tetrahymena pyriformis and the bacterium Alicyclobacillus acidocaldarius normally convert squalene into pentacyclic triterpenes of the gammacerane and hopane
Biosynthesis of (+)-cubenene and (+)-epicubenol by cell-free extracts of cultured cells of Heteroscyphus planus and cyclization of [^2H]farnesyl diphosphates
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
Enzymatic cyclization of all-trans pentaprenyl and hexaprenyl methyl ethers by a cell-free system from the protozoon Tetrahymena pyriformis. The biosynthesis of scalarane and polycyclohexaprenyl derivatives.
The cyclization of hexaprenyl methyl ether is the first attempt of identification of these tricyclopolyprenol derivatives in living organisms.