@article{oai:niigata-u.repo.nii.ac.jp:00002231,
 author = {Hoshino, Tsutomu and Nakano, Schin-ichi and Kondo, Tomohiro and Sato, Tsutomu and Miyoshi, Aya},
 journal = {Organic & biomolecular chemistry, Organic & biomolecular chemistry},
 month = {Dec},
 note = {To provide insight into the polycyclization mechanism of squalene by squalene–hopene cyclase (SHC) from Alicyclobacilus acidocaldarius, some analogs of nor- and bisnorsqualenes were synthesized including the deuterium-labeled squalenes and incubated with the wild-type SHC, leading to the following inferences. (1) The deprotonation reaction for the introduction of the double bond of the hopene skeleton occurs exclusively from the Z-methyl group on the terminal double bond of squalene. (2) 3R-Oxidosqualene was folded in a boat conformation for the A-ring construction, while the 3S-form was in a chair structure. (3) The terminal two methyl groups are indispensable both for the formation of the 5-membered E-ring of the hopene skeleton and for the initiation of the polycyclization cascade, but the terminal Z-methyl group has a more crucial role for the construction of the 5-membered E-ring than the E-methyl group. (4) Some of the novel terpene skeletons, 36, 37, 39 and 40, were created from the analogs employed in this investigation.},
 pages = {1456--1470},
 title = {Squalene–hopene cyclase : final deprotonation reaction, conformational analysis for the cyclization of (3R,S)-2,3-oxidosqualene and further evidence for the requirement of an isopropylidene moiety both for initiation of the polycyclization cascade and for the formation of the 5-membered E-ring},
 volume = {2},
 year = {2004}
}