Prenylation of a nonaromatic carbon of indolylbutenone by a fungal indole prenyltransferase

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

doi:10.1021/ol301129x

Prenylation of a nonaromatic carbon of indolylbutenone by a fungal indole prenyltransferase

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

^*この論文の責任著者

和漢医薬学総合研究所研究開発部門資源開発分野（天然物創薬学領域）

研究成果: ジャーナルへの寄稿 › 学術論文 › 査読

27 被引用数 (Scopus)

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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.

本文言語	英語
ページ（範囲）	3080-3083
ページ数	4
ジャーナル	Organic Letters
巻	14
号	12
DOI	https://doi.org/10.1021/ol301129x
出版ステータス	出版済み - 2012/06/15

ASJC Scopus 主題領域

生化学
物理化学および理論化学
有機化学

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10.1021/ol301129x

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title = "Prenylation of a nonaromatic carbon of indolylbutenone by a fungal indole prenyltransferase",

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.",

author = "Jing Chen and Hiroyuki Morita and Toshiyuki Wakimoto and Takahiro Mori and Hiroshi Noguchi and Ikuro Abe",

year = "2012",

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doi = "10.1021/ol301129x",

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T1 - Prenylation of a nonaromatic carbon of indolylbutenone by a fungal indole prenyltransferase

AU - Chen, Jing

AU - Morita, Hiroyuki

AU - Wakimoto, Toshiyuki

AU - Mori, Takahiro

AU - Noguchi, Hiroshi

AU - Abe, Ikuro

PY - 2012/6/15

Y1 - 2012/6/15

N2 - 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.

AB - 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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U2 - 10.1021/ol301129x

DO - 10.1021/ol301129x

M3 - 学術論文

C2 - 22642693

AN - SCOPUS:84862581870

SN - 1523-7060

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SP - 3080

EP - 3083

JO - Organic Letters

JF - Organic Letters

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Prenylation of a nonaromatic carbon of indolylbutenone by a fungal indole prenyltransferase

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