Stereochemical course in water addition during LUP1-catalyzed triterpene cyclization

Tetsuo Kushiro, Masaki Hoshino, Takehiko Tsutsumi, Ken Ichi Kawai, Motoo Shiro, Masaaki Shibuya, Yutaka Ebizuka

Research output: Contribution to journalArticlepeer-review

11 Citations (Scopus)


Arabidopsis thaliana LUP1 (At1g78970) catalyzes the cyclization of oxidosqualene into lupeol and 3β,20-dihydroxylupane (lupanediol). The stereochemical course of water addition to the lupanyl cation was studied. The X-ray crystal structure of lupanylepoxide 3,5-dinitrobenzoate established the configuration of epoxide as 20S. LiAID4 reduction of the epoxide enabled the chemical shift assignment of prochiral methyl groups at C20 of lupanediol. Correlation of these methyl groups with biosynthetic lupanediol from [1,2-13C2] acetate established the stereochemical course of water addition.

Original languageEnglish
Pages (from-to)5589-5592
Number of pages4
JournalOrganic Letters
Issue number24
Publication statusPublished - 23 Nov 2006


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