Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 133, Issue 32, Pages 12342-12345Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja2034969
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- National Sciences and Engineering Research Council of Canada (NSERC)
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The enzyme dimethylallyltryptophan synthase catalyzes the normal prenylation of Tip 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.
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