A Cope Rearrangement in the Reaction Catalyzed by Dimethylallyltryptophan Synthase?

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• 作者：Louis Y. P. Luk ; Qi Qian ; Martin E. Tanner
• 刊名：Journal of the American Chemical Society
• 出版年：2011
• 出版时间：August 17, 2011
• 年：2011
• 卷：133
• 期：32
• 页码：12342-12345
• 全文大小：736K
• 年卷期：v.133,no.32(August 17, 2011)
• ISSN：1520-5126

文摘

The enzyme dimethylallyltryptophan synthase catalyzes the 鈥渘ormal鈥?prenylation of Trp at C-4 in the first step of ergot alkaloid biosynthesis. The Lys174Ala mutant is found to produce a hexahydropyrroloindole alkaloid that is 鈥渞everse-prenylated鈥?at C-3 as its major product. This is interpreted as evidence in support of a mechanism that involves an initial 鈥渞everse-prenylation鈥?at C-3, followed by a Cope rearrangement and rearomatization.