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

Author:
Chen, Jing, Morita, Hiroyuki, Wakimoto, Toshiyuki, Mori, Takahiro, Noguchi, Hiroshi, Abe, Ikuro
Source:
Organic letters 2012 v.14 no.12 pp. 3080-3083
ISSN:
1523-7052
Subject:
Aspergillus fumigatus, carbon, chemical reactions, chemical structure, fungi, organic compounds, regioselectivity
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.
Agid:
5783923