2003•Journal of Labelled Compounds and RadiopharmaceuticalsRequires access

Asymmetric epoxidation of digeranyl by cultured cells of Nicotiana tabacum

Osamu Nakagawa, Kei Shimoda, Sunsuke Izumi, Toshifumi Hirata

Abstract

Abstract Asymmetric epoxidation of digeranyl, which is a squalene analog, with cultured cells of Nicotiana tabacum was investigated. Feeding of [8‐3H]‐digeranyl into the cultured cells of N. tabacum resulted in the formation of (3S)‐2,3‐epoxydigeranyl and 6,7‐epoxydigeranyl. It was found that the epoxidation of digeranyl with N. tabacum was highly stereoselective. Copyright © 2003 John Wiley & Sons, Ltd.

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Key concepts: Nicotiana tabacum, Chemistry, Squalene, Stereoselectivity, Stereochemistry, Botany, Biochemistry, Gene