期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 133, 期 32, 页码 12342-12345出版社
AMER CHEMICAL SOC
DOI: 10.1021/ja2034969
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资金
- National Sciences and Engineering Research Council of Canada (NSERC)
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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