Detection of 1,2-hydride shifts in the formation of euph-7-ene by the squalene-tetrahymanol cyclase of Tetrahymena pyriformis.
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.
Giner
José-Luis
JL
Laboratorium für Organische Chemie, ETH-Hönggerberg HCI H307, CH-8093, Zürich, Switzerland.
Rocchetti
Stefano
S
Neunlist
Serge
S
Rohmer
Michel
M
Arigoni
Duilio
D
D000818:Animals; D003903:Deuterium; D008190:Lyases / Q000378:metabolism*; D013185:Squalene / Q000031:analogs & derivatives* / Q000378:metabolism; D013769:Tetrahymena pyriformis / Q000201:enzymology*; D014315:Triterpenes / Q000378:metabolism
D014315:Triterpenes; C517934:euph-7-ene; D013185:Squalene; D003903:Deuterium; D008190:Lyases; C022651:squalene cyclase