Organic Letters

, volume 23 , issue 5 , pages 1904-1909

An Enzyme-Mediated Aza-Michael Addition Is Involved in the Biosynthesis of an Imidazoyl Hybrid Product of Conidiogenone B

Ranuka T Hewage ^{1, 2, 3}

Rou Jie Huang ³

Shu-Jung Lai ^{1, 4, 5}

Ya Chu Lien ¹

Shao-Hsing Weng ⁶

Dehai Li ⁷

Yu-Ju Chen ⁶

Shih-Tse Wu ^{1, 2, 3}

Rong Jie Chein ^{2, 6}

Hsiao-Ching Lin ^{1, 2}

Hide authors affiliations Show authors affiliations: 7 affiliations

Institute of Biological Chemistry, Academia  Sinica, Taipei 115, Taiwan R.O.C. |

Chemical Biology and Molecular Biophysics Program, Taiwan International Graduate Program, Academia Sinica, Taipei 115, Taiwan R.O.C. |

Department of Chemistry, National Taiwan University, Taipei 106, Taiwan R.O.C. |

⁴

Graduate Institute of Biomedical Sciences, China Medical University, Taichung 404, Taiwan R.O.C. |

⁵

Research Center for Cancer Biology, China Medical University, Taichung 404, Taiwan R.O.C. |

⁶

Institute of Chemistry,  Academia Sinica, Taipei 115, Taiwan R.O.C. |

⁷

Key Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, P.R. China |

Publication type: Journal Article

Publication date: 2021-02-11

American Chemical Society (ACS)

Organic Letters

scimago Q1

wos Q1

SJR: 1.235

CiteScore: 8.7

Impact factor: 5.0

ISSN: 15237060, 15237052

DOI: 10.1021/acs.orglett.1c00330

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PubMed ID: 33570417

Organic Chemistry

Biochemistry

Physical and Theoretical Chemistry

Abstract

Meleagrin B is a terpene-alkaloid hybrid natural product that contains both the conidiogenone and meleagrin scaffold. Their derivatives show diverse biological activities. We characterized the biosynthesis of (-)-conidiogenone B (1), which involves a diterpene synthase and a P450 monooxygenase. In addition, an α,β-hydrolase (Con-ABH) was shown to catalyze an aza-Michael addition between 1 and imidazole to give 3S-imidazolyl conidiogenone B (6). Compound 6 was more potent than 1 against Staphylococcus aureus strains.

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GOST Copy

Hewage R. T. et al. An Enzyme-Mediated Aza-Michael Addition Is Involved in the Biosynthesis of an Imidazoyl Hybrid Product of Conidiogenone B // Organic Letters. 2021. Vol. 23. No. 5. pp. 1904-1909.

GOST all authors (up to 50) Copy

Hewage R. T., Huang R. J., Lai S., Lien Ya. C., Weng S., Li D., Chen Y., Wu S., Chein R. J., Lin H. An Enzyme-Mediated Aza-Michael Addition Is Involved in the Biosynthesis of an Imidazoyl Hybrid Product of Conidiogenone B // Organic Letters. 2021. Vol. 23. No. 5. pp. 1904-1909.

RIS |

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RIS Copy

TY - JOUR

DO - 10.1021/acs.orglett.1c00330

UR - https://doi.org/10.1021/acs.orglett.1c00330

TI - An Enzyme-Mediated Aza-Michael Addition Is Involved in the Biosynthesis of an Imidazoyl Hybrid Product of Conidiogenone B

T2 - Organic Letters

AU - Hewage, Ranuka T

AU - Huang, Rou Jie

AU - Lai, Shu-Jung

AU - Lien, Ya Chu

AU - Weng, Shao-Hsing

AU - Li, Dehai

AU - Chen, Yu-Ju

AU - Wu, Shih-Tse

AU - Chein, Rong Jie

AU - Lin, Hsiao-Ching

PY - 2021

DA - 2021/02/11

PB - American Chemical Society (ACS)

SP - 1904-1909

IS - 5

VL - 23

PMID - 33570417

SN - 1523-7060

SN - 1523-7052

ER -

BibTex |

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BibTex (up to 50 authors) Copy

@article{2021_Hewage,

author = {Ranuka T Hewage and Rou Jie Huang and Shu-Jung Lai and Ya Chu Lien and Shao-Hsing Weng and Dehai Li and Yu-Ju Chen and Shih-Tse Wu and Rong Jie Chein and Hsiao-Ching Lin},

title = {An Enzyme-Mediated Aza-Michael Addition Is Involved in the Biosynthesis of an Imidazoyl Hybrid Product of Conidiogenone B},

journal = {Organic Letters},

year = {2021},

volume = {23},

publisher = {American Chemical Society (ACS)},

month = {feb},

url = {https://doi.org/10.1021/acs.orglett.1c00330},

number = {5},

pages = {1904--1909},

doi = {10.1021/acs.orglett.1c00330}

}

MLA

Cite this

MLA Copy

Hewage, Ranuka T., et al. “An Enzyme-Mediated Aza-Michael Addition Is Involved in the Biosynthesis of an Imidazoyl Hybrid Product of Conidiogenone B.” Organic Letters, vol. 23, no. 5, Feb. 2021, pp. 1904-1909. https://doi.org/10.1021/acs.orglett.1c00330.

Publisher

American Chemical Society (ACS)

Journal

Organic Letters

scimago Q1

wos Q1

SJR

1.235

CiteScore

8.7

Impact factor

5.0

ISSN

15237060 (Print)

15237052 (Electronic)