Stereochemical Course in Water Addition during LUP1-Catalyzed Triterpene Cyclization

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 config...

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Veröffentlicht in:	Organic letters 2006-11, Vol.8 (24), p.5589-5592
Hauptverfasser:	Kushiro, Tetsuo, Hoshino, Masaki, Tsutsumi, Takehiko, Kawai, Ken-ichi, Shiro, Motoo, Shibuya, Masaaki, Ebizuka, Yutaka
Format:	Artikel
Sprache:	eng
Schlagworte:	Arabidopsis Proteins - chemistry Crystallography, X-Ray Cyclization Intramolecular Transferases - chemistry Magnetic Resonance Spectroscopy Molecular Conformation Oxidation-Reduction Stereoisomerism Triterpenes - chemical synthesis Water - chemistry
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Zusammenfassung:	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. LiAlD4 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.
ISSN:	1523-7060 1523-7052
DOI:	10.1021/ol062310d