Prenylation of a Nonaromatic Carbon of Indolylbutenone by a Fungal Indole Prenyltransferase

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.

Jing Chen, Hiroyuki Morita, Toshiyuki Wakimoto, Takahiro Mori, Hiroshi Noguchi, Ikuro Abe

Organic Letters

2012, 14, 3080