Dual Engineering of Olivetolic Acid Cyclase and Tetraketide Synthase to Generate Longer Alkyl-Chain Olivetolic Acid Analogs

Yuan E. Lee; Yu Nakashima; Takeshi Kodama; Xinrui Chen; Hiroyuki Morita

doi:10.1021/acs.orglett.1c04089

Dual Engineering of Olivetolic Acid Cyclase and Tetraketide Synthase to Generate Longer Alkyl-Chain Olivetolic Acid Analogs

Yuan E. Lee, Yu Nakashima, Takeshi Kodama, Xinrui Chen, Hiroyuki Morita^*

^*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

8 被引用数 (Scopus)

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The therapeutic effects of Δ⁹-tetrahydrocannabinol (Δ⁹-THC) can be enhanced by modifications of the pentyl moiety at C-3. The engineering of Cannabis sativa olivetolic acid cyclase and tetraketide synthase with F24I and L190G substitutions, respectively, in the biosynthesis of Δ⁹-THC serves as a platform for the generation of resorcylic acids up to 6-undecylresorcylic acid. These results provide insights into the development of THC analogs with chemically distinct acyl moieties at C-3.

本文言語	英語
ページ（範囲）	410-414
ページ数	5
ジャーナル	Organic Letters
巻	24
号	1
DOI	https://doi.org/10.1021/acs.orglett.1c04089
出版ステータス	出版済み - 2022/01/14

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.1c04089

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title = "Dual Engineering of Olivetolic Acid Cyclase and Tetraketide Synthase to Generate Longer Alkyl-Chain Olivetolic Acid Analogs",

abstract = "The therapeutic effects of Δ9-tetrahydrocannabinol (Δ9-THC) can be enhanced by modifications of the pentyl moiety at C-3. The engineering of Cannabis sativa olivetolic acid cyclase and tetraketide synthase with F24I and L190G substitutions, respectively, in the biosynthesis of Δ9-THC serves as a platform for the generation of resorcylic acids up to 6-undecylresorcylic acid. These results provide insights into the development of THC analogs with chemically distinct acyl moieties at C-3.",

author = "Lee, {Yuan E.} and Yu Nakashima and Takeshi Kodama and Xinrui Chen and Hiroyuki Morita",

note = "Publisher Copyright: {\textcopyright} 2021 American Chemical Society",

year = "2022",

month = jan,

day = "14",

doi = "10.1021/acs.orglett.1c04089",

language = "英語",

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T1 - Dual Engineering of Olivetolic Acid Cyclase and Tetraketide Synthase to Generate Longer Alkyl-Chain Olivetolic Acid Analogs

AU - Lee, Yuan E.

AU - Nakashima, Yu

AU - Kodama, Takeshi

AU - Chen, Xinrui

AU - Morita, Hiroyuki

PY - 2022/1/14

Y1 - 2022/1/14

N2 - The therapeutic effects of Δ9-tetrahydrocannabinol (Δ9-THC) can be enhanced by modifications of the pentyl moiety at C-3. The engineering of Cannabis sativa olivetolic acid cyclase and tetraketide synthase with F24I and L190G substitutions, respectively, in the biosynthesis of Δ9-THC serves as a platform for the generation of resorcylic acids up to 6-undecylresorcylic acid. These results provide insights into the development of THC analogs with chemically distinct acyl moieties at C-3.

AB - The therapeutic effects of Δ9-tetrahydrocannabinol (Δ9-THC) can be enhanced by modifications of the pentyl moiety at C-3. The engineering of Cannabis sativa olivetolic acid cyclase and tetraketide synthase with F24I and L190G substitutions, respectively, in the biosynthesis of Δ9-THC serves as a platform for the generation of resorcylic acids up to 6-undecylresorcylic acid. These results provide insights into the development of THC analogs with chemically distinct acyl moieties at C-3.

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U2 - 10.1021/acs.orglett.1c04089

DO - 10.1021/acs.orglett.1c04089

M3 - 学術論文

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AN - SCOPUS:85122593923

SN - 1523-7060

VL - 24

SP - 410

EP - 414

JO - Organic Letters

JF - Organic Letters

IS - 1

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Dual Engineering of Olivetolic Acid Cyclase and Tetraketide Synthase to Generate Longer Alkyl-Chain Olivetolic Acid Analogs

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