Mechanistic studies on the indole prenyltransferases

Covering: up to 2014 Prenylated indole alkaloids comprise a large and structurally diverse family of natural products that often display potent biological activities. In recent years a large family of prenyltransferases that install prenyl groups onto the indole core have been discovered. While the...

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Bibliographic Details
Published in:Natural product reports 2015-01, Vol.32 (1), p.88-11
Main Author: Tanner, Martin E
Format: Article
Language:English
Subjects:
Biological Products
Dimethylallyltranstransferase
Indole Alkaloids
Molecular Structure
Prenylation
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Summary:Covering: up to 2014 Prenylated indole alkaloids comprise a large and structurally diverse family of natural products that often display potent biological activities. In recent years a large family of prenyltransferases that install prenyl groups onto the indole core have been discovered. While the vast majority of these enzymes are evolutionarily related and share a common protein fold, they are remarkably versatile in their ability to catalyze reverse and normal prenylations at all positions on the indole ring. This highlight article will focus on recent studies of the mechanisms utilized by indole prenyltransferases. While all of the prenylation reactions may follow a direct electrophilic aromatic substitution mechanism, studies of structure and reactivity suggest that in some cases prenylation may first occur at the nucleophilic C-3 position, and subsequent rearrangements then generate the final product. This review article presents a review of recent mechanistic studies on the reactions catalyzed by the soluble indole prenyltransferases.
ISSN:0265-0568
1460-4752
DOI:10.1039/c4np00099d