Combinatorial Biosynthesis of (+)-Daurichromenic Acid and Its Halogenated Analogue

Masahiro Okada; Kai Saito; Chin Piow Wong; Chang Li; Dongmei Wang; Miu Iijima; Futoshi Taura; Fumiya Kurosaki; Takayoshi Awakawa; Ikuro Abe

doi:10.1021/acs.orglett.7b01288

Combinatorial Biosynthesis of (+)-Daurichromenic Acid and Its Halogenated Analogue

Masahiro Okada^*, Kai Saito, Chin Piow Wong, Chang Li, Dongmei Wang, Miu Iijima, Futoshi Taura, Fumiya Kurosaki, Takayoshi Awakawa, Ikuro Abe

^*この論文の責任著者

薬用生物資源学研究室

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)

抄録

Daurichromenic acid is a meroterpenoid with various pharmacological activities that is biosynthesized from grifolic acid in Rhododendron dauricum. Heterologous expression of grifolic acid synthases from Stachybotrys bisbyi and a daurichromenic acid synthase from R. dauricum in Aspergillus oryzae mediated three-step combinatorial biosynthesis of (+)-daurichromenic acid through enantioselective 6-endo-trig cyclization. Additional introduction of a halogenase from Fusarium sp. into the strain resulted in the biosynthesis of (+)-5-chlorodaurichromenic acid, which exceeds the antibacterial activity of the original compounds.

本文言語	英語
ページ（範囲）	3183-3186
ページ数	4
ジャーナル	Organic Letters
巻	19
号	12
DOI	https://doi.org/10.1021/acs.orglett.7b01288
出版ステータス	出版済み - 2017/06/16

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/acs.orglett.7b01288

引用スタイル

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title = "Combinatorial Biosynthesis of (+)-Daurichromenic Acid and Its Halogenated Analogue",

abstract = "Daurichromenic acid is a meroterpenoid with various pharmacological activities that is biosynthesized from grifolic acid in Rhododendron dauricum. Heterologous expression of grifolic acid synthases from Stachybotrys bisbyi and a daurichromenic acid synthase from R. dauricum in Aspergillus oryzae mediated three-step combinatorial biosynthesis of (+)-daurichromenic acid through enantioselective 6-endo-trig cyclization. Additional introduction of a halogenase from Fusarium sp. into the strain resulted in the biosynthesis of (+)-5-chlorodaurichromenic acid, which exceeds the antibacterial activity of the original compounds.",

author = "Masahiro Okada and Kai Saito and Wong, {Chin Piow} and Chang Li and Dongmei Wang and Miu Iijima and Futoshi Taura and Fumiya Kurosaki and Takayoshi Awakawa and Ikuro Abe",

note = "Publisher Copyright: {\textcopyright} 2017 American Chemical Society.",

year = "2017",

month = jun,

day = "16",

doi = "10.1021/acs.orglett.7b01288",

language = "英語",

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T1 - Combinatorial Biosynthesis of (+)-Daurichromenic Acid and Its Halogenated Analogue

AU - Okada, Masahiro

AU - Saito, Kai

AU - Wong, Chin Piow

AU - Li, Chang

AU - Wang, Dongmei

AU - Iijima, Miu

AU - Taura, Futoshi

AU - Kurosaki, Fumiya

AU - Awakawa, Takayoshi

AU - Abe, Ikuro

PY - 2017/6/16

Y1 - 2017/6/16

N2 - Daurichromenic acid is a meroterpenoid with various pharmacological activities that is biosynthesized from grifolic acid in Rhododendron dauricum. Heterologous expression of grifolic acid synthases from Stachybotrys bisbyi and a daurichromenic acid synthase from R. dauricum in Aspergillus oryzae mediated three-step combinatorial biosynthesis of (+)-daurichromenic acid through enantioselective 6-endo-trig cyclization. Additional introduction of a halogenase from Fusarium sp. into the strain resulted in the biosynthesis of (+)-5-chlorodaurichromenic acid, which exceeds the antibacterial activity of the original compounds.

AB - Daurichromenic acid is a meroterpenoid with various pharmacological activities that is biosynthesized from grifolic acid in Rhododendron dauricum. Heterologous expression of grifolic acid synthases from Stachybotrys bisbyi and a daurichromenic acid synthase from R. dauricum in Aspergillus oryzae mediated three-step combinatorial biosynthesis of (+)-daurichromenic acid through enantioselective 6-endo-trig cyclization. Additional introduction of a halogenase from Fusarium sp. into the strain resulted in the biosynthesis of (+)-5-chlorodaurichromenic acid, which exceeds the antibacterial activity of the original compounds.

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U2 - 10.1021/acs.orglett.7b01288

DO - 10.1021/acs.orglett.7b01288

M3 - 学術論文

C2 - 28541042

AN - SCOPUS:85020893472

SN - 1523-7060

VL - 19

SP - 3183

EP - 3186

JO - Organic Letters

JF - Organic Letters

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Combinatorial Biosynthesis of (+)-Daurichromenic Acid and Its Halogenated Analogue

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