A cope rearrangement in the reaction catalyzed by dimethylallyltryptophan synthase?

Luk, Louis Yu Pan ORCID: https://orcid.org/0000-0002-7864-6261, 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:	Schools > Chemistry
Subjects:	Q Science > QD Chemistry
Publisher:	American Chemical Society
ISSN:	0002-7863
Last Modified:	24 Oct 2022 10:59
URI:	https://orca.cardiff.ac.uk/id/eprint/46576

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