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

被引:45
作者
Hoshino, T [1 ]
Kouda, M
Abe, T
Ohashi, S
机构
[1] Niigata Univ, Fac Agr, Dept Appl Biol Chem, Niigata 9502181, Japan
[2] Niigata Univ, Grad Sch Sci & Technol, Niigata 9502181, Japan
关键词
squalene; hopene; triterpene cyclase; 2,3-oxidosqualene;
D O I
10.1271/bbb.63.2038
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
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.
引用
收藏
页码:2038 / 2041
页数:4
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