Prenylation of a nonaromatic carbon of indolylbutenone by a fungal indole prenyltransferase - PubMed (original) (raw)
. 2012 Jun 15;14(12):3080-3.
doi: 10.1021/ol301129x. Epub 2012 May 30.
Affiliations
- PMID: 22642693
- DOI: 10.1021/ol301129x
Prenylation of a nonaromatic carbon of indolylbutenone by a fungal indole prenyltransferase
Jing Chen et al. Org Lett. 2012.
Abstract
FtmPT1 from Aspergillus fumigatus is a fungal indole prenyltransferase (PT) that normally catalyzes the regiospecific prenylation of brevianamide F (cyclo-L-Trp-L-Pro) at the C-2 position of the indole ring with dimethylallyl diphosphate (DMAPP). Interestingly, FtmPT1 exhibited remarkable substrate tolerance and accepted (E)-4-(1H-indol-3-yl)but-3-en-2-one (1) as a substrate to produce an unnatural novel α-prenylindolylbutenone (1a). This is the first demonstration of the prenylation of a nonaromatic carbon of the acceptor substrate by a fungal indole PT.
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