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A cope rearrangement in the reaction catalyzed by dimethylallyltryptophan synthase?

Luk, Louis Yu Pan, Qian, Qi and Tanner, Martin E. 2011. A cope rearrangement in the reaction catalyzed by dimethylallyltryptophan synthase? Journal of the American Chemical Society 133 (32) , pp. 12342-12345. 10.1021/ja2034969

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Abstract

The enzyme dimethylallyltryptophan synthase catalyzes the “normal” 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 “reverse-prenylated” at C-3 as its major product. This is interpreted as evidence in support of a mechanism that involves an initial “reverse-prenylation” at C-3, followed by a Cope rearrangement and rearomatization.

Item Type: Article
Date Type: Publication
Status: Published
Schools: Chemistry
Subjects: Q Science > QD Chemistry
Publisher: American Chemical Society
ISSN: 0002-7863
Last Modified: 04 Jun 2017 04:56
URI: http://orca.cf.ac.uk/id/eprint/46576

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