Enzymatic formation of unnatural novel polyketide scaffolds by plant-specific type III polyketide synthase

She Po Shi; Hiroyuki Morita; Kiyofumi Wanibuchi; Hiroshi Noguchi; Ikuro Abe

doi:10.1016/j.tetlet.2009.02.170

Enzymatic formation of unnatural novel polyketide scaffolds by plant-specific type III polyketide synthase

She Po Shi, Hiroyuki Morita, Kiyofumi Wanibuchi, 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

5 被引用数 (Scopus)

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The catalytic potential of octaketide synthase (OKS), a plant-specific type III polyketide synthase (PKS) from Aloe arborescens, was investigated by phenylacetyl-CoA and benzoyl-CoA as starter substrates. As a result, a novel C₁₆ pentaketide coumarin was produced from phenylacetyl-CoA, whereas benzoyl-CoA was not a good substrate of OKS. Remarkably, a structure-guided OKS N222G mutant dramatically extended the product chain length to yield four novel polyketides including C₂₂ aromatic octaketides from the C₆-C₂ phenylacetyl starter, as well as a novel C₁₉ heptaketide benzophenone from the C₆-C₁ benzoyl starter.

本文言語	英語
ページ（範囲）	2150-2153
ページ数	4
ジャーナル	Tetrahedron Letters
巻	50
号	18
DOI	https://doi.org/10.1016/j.tetlet.2009.02.170
出版ステータス	出版済み - 2009/05/06

ASJC Scopus 主題領域

生化学
創薬
有機化学

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10.1016/j.tetlet.2009.02.170

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@article{b6428cb7b96e4349a314673c67f38660,

title = "Enzymatic formation of unnatural novel polyketide scaffolds by plant-specific type III polyketide synthase",

abstract = "The catalytic potential of octaketide synthase (OKS), a plant-specific type III polyketide synthase (PKS) from Aloe arborescens, was investigated by phenylacetyl-CoA and benzoyl-CoA as starter substrates. As a result, a novel C16 pentaketide coumarin was produced from phenylacetyl-CoA, whereas benzoyl-CoA was not a good substrate of OKS. Remarkably, a structure-guided OKS N222G mutant dramatically extended the product chain length to yield four novel polyketides including C22 aromatic octaketides from the C6-C2 phenylacetyl starter, as well as a novel C19 heptaketide benzophenone from the C6-C1 benzoyl starter.",

author = "Shi, {She Po} and Hiroyuki Morita and Kiyofumi Wanibuchi and Hiroshi Noguchi and Ikuro Abe",

note = "Funding Information: This work was supported by the PRESTO program from Japan Science and Technology Agency, Grant-in-Aid scientific Research from the Ministry of Education, Culture, Sports, Science and Technology, Japan, and Research Grants from the Astellas Foundation for Research on Metabolic Disorders, and the Uehara Memorial Foundation, Japan. S.-P.S. and K.W. are recipients of the JSPS Postdoctoral Fellowship for Foreign Researchers (no. P07048) and the JSPS Fellowship for Young Scientists (no. 207112), respectively. ",

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doi = "10.1016/j.tetlet.2009.02.170",

language = "英語",

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T1 - Enzymatic formation of unnatural novel polyketide scaffolds by plant-specific type III polyketide synthase

AU - Shi, She Po

AU - Morita, Hiroyuki

AU - Wanibuchi, Kiyofumi

AU - Noguchi, Hiroshi

AU - Abe, Ikuro

N1 - Funding Information: This work was supported by the PRESTO program from Japan Science and Technology Agency, Grant-in-Aid scientific Research from the Ministry of Education, Culture, Sports, Science and Technology, Japan, and Research Grants from the Astellas Foundation for Research on Metabolic Disorders, and the Uehara Memorial Foundation, Japan. S.-P.S. and K.W. are recipients of the JSPS Postdoctoral Fellowship for Foreign Researchers (no. P07048) and the JSPS Fellowship for Young Scientists (no. 207112), respectively.

PY - 2009/5/6

Y1 - 2009/5/6

N2 - The catalytic potential of octaketide synthase (OKS), a plant-specific type III polyketide synthase (PKS) from Aloe arborescens, was investigated by phenylacetyl-CoA and benzoyl-CoA as starter substrates. As a result, a novel C16 pentaketide coumarin was produced from phenylacetyl-CoA, whereas benzoyl-CoA was not a good substrate of OKS. Remarkably, a structure-guided OKS N222G mutant dramatically extended the product chain length to yield four novel polyketides including C22 aromatic octaketides from the C6-C2 phenylacetyl starter, as well as a novel C19 heptaketide benzophenone from the C6-C1 benzoyl starter.

AB - The catalytic potential of octaketide synthase (OKS), a plant-specific type III polyketide synthase (PKS) from Aloe arborescens, was investigated by phenylacetyl-CoA and benzoyl-CoA as starter substrates. As a result, a novel C16 pentaketide coumarin was produced from phenylacetyl-CoA, whereas benzoyl-CoA was not a good substrate of OKS. Remarkably, a structure-guided OKS N222G mutant dramatically extended the product chain length to yield four novel polyketides including C22 aromatic octaketides from the C6-C2 phenylacetyl starter, as well as a novel C19 heptaketide benzophenone from the C6-C1 benzoyl starter.

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M3 - 学術論文

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SN - 0040-4039

VL - 50

SP - 2150

EP - 2153

JO - Tetrahedron Letters

JF - Tetrahedron Letters

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ER -

Enzymatic formation of unnatural novel polyketide scaffolds by plant-specific type III polyketide synthase

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