New cyclization mechanism for squalene: a ring-expansion step for the five-membered C-ring intermediate in hopene biosynthesis.

Abstract

Three triterpenes having the 6/6/5-fused tri- and 6/6/6/5-fused tetracyclic skeletons were isolated from an incubation mixture of the mutated F601A enzyme, these products being in accordance with a Markovnikov closure. Successful trapping of the tricyclic cationic intermediate by using the squalene analog having a highly nucleophilic hydroxyl group leads us to propose that the ring expansion process of the 5-membered C-ring is involved in the squalene cyclization cascade.

Cite this paper

@article{Hoshino1999NewCM, title={New cyclization mechanism for squalene: a ring-expansion step for the five-membered C-ring intermediate in hopene biosynthesis.}, author={Tsutomu Hoshino and Masanori Kouda and Toshiaki Abe and Shinya Ohashi}, journal={Bioscience, biotechnology, and biochemistry}, year={1999}, volume={63 11}, pages={2038-41} }