| Literature DB >> 21766851 |
Louis Y P Luk1, Qi Qian, Martin E Tanner.
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.Entities:
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Year: 2011 PMID： 21766851 DOI： 10.1021/ja2034969
Source DB: PubMed Journal: J Am Chem Soc ISSN： 0002-7863 Impact factor: 15.419