Collect. Czech. Chem. Commun. 2008, 73, 786-794

The Concerted Nature of the Enzymatic Cyclization of Rings A-D of Squalene to Hopene

B. Andes Hess, Jr.a,* and Lidia Smenteka,b

a Department of Chemistry, Vanderbilt University, Nashville, Tennessee 37235, U.S.A.
b Institute of Physics, N. Copernicus University, 87-100 Toruń, Poland


A conformational analysis of squalene encapsulated in squalene-hopene cyclase has been performed based on Schulz's X-ray structure and our DFT calculations. Based on this analysis it is concluded that the formation of rings A-D in the cyclization of squalene are likely to be a concerted but highly asynchronous reaction.

Keywords: Squalene; Steroid biosynthesis; Hopene; Carbocation cyclizations.

References: 19 live references.