Biosynthesis of Atypical Angucyclines Unveils New Ring Rearrangement Reactions Catalyzed by Flavoprotein Monooxygenases

Xiao Xu; Yimin Chang; Yinghan Chen; Luning Zhou; Falei Zhang; Chuanteng Ma; Qian Che; Tianjiao Zhu; Blaine A. Pfeifer; Guojian Zhang; Dehai Li

doi:10.1021/acs.orglett.4c02074

Biosynthesis of Atypical Angucyclines Unveils New Ring Rearrangement Reactions Catalyzed by Flavoprotein Monooxygenases

Xiao Xu
, Yimin Chang
, Yinghan Chen
, Luning Zhou
, Falei Zhang
, Chuanteng Ma
, Qian Che
, Tianjiao Zhu
, Blaine A. Pfeifer
, Guojian Zhang
, Dehai Li

Department of Chemical and Biological Engineering

Ocean University of China
Qingdao Marine Science and Technology Center
Marine Biomedical Research Institute of Qingdao

Research output: Contribution to journal › Article › peer-review

10 Scopus citations

Abstract

Six new angucycline structures, including spirocyclione A (1), which contains an unusual oxaspiro[5.5]undecane architecture, and its ring-A-cleaved product spirocyclione B (2), were discovered by heterologous expression of a type II polyketide biosynthetic gene cluster captured from a marine actinomycete strain Streptomyces sp. HDN155000. Three flavoprotein monooxygenases are confirmed to be responsible for the oxidative carbon skeleton rearrangements in the biosynthesis of compounds 1 and 2. The obtained compounds showed promising cytotoxicity against different types of cancer cells.

Original language	English
Pages (from-to)	7489-7494
Number of pages	6
Journal	Organic Letters
Volume	26
Issue number	36
DOIs	https://doi.org/10.1021/acs.orglett.4c02074
State	Published - Sep 13 2024

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abstract = "Six new angucycline structures, including spirocyclione A (1), which contains an unusual oxaspiro[5.5]undecane architecture, and its ring-A-cleaved product spirocyclione B (2), were discovered by heterologous expression of a type II polyketide biosynthetic gene cluster captured from a marine actinomycete strain Streptomyces sp. HDN155000. Three flavoprotein monooxygenases are confirmed to be responsible for the oxidative carbon skeleton rearrangements in the biosynthesis of compounds 1 and 2. The obtained compounds showed promising cytotoxicity against different types of cancer cells.",

author = "Xiao Xu and Yimin Chang and Yinghan Chen and Luning Zhou and Falei Zhang and Chuanteng Ma and Qian Che and Tianjiao Zhu and Pfeifer, \{Blaine A.\} and Guojian Zhang and Dehai Li",

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doi = "10.1021/acs.orglett.4c02074",

language = "English",

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T1 - Biosynthesis of Atypical Angucyclines Unveils New Ring Rearrangement Reactions Catalyzed by Flavoprotein Monooxygenases

AU - Xu, Xiao

AU - Chang, Yimin

AU - Chen, Yinghan

AU - Zhou, Luning

AU - Zhang, Falei

AU - Ma, Chuanteng

AU - Che, Qian

AU - Zhu, Tianjiao

AU - Pfeifer, Blaine A.

AU - Zhang, Guojian

AU - Li, Dehai

PY - 2024/9/13

Y1 - 2024/9/13

N2 - Six new angucycline structures, including spirocyclione A (1), which contains an unusual oxaspiro[5.5]undecane architecture, and its ring-A-cleaved product spirocyclione B (2), were discovered by heterologous expression of a type II polyketide biosynthetic gene cluster captured from a marine actinomycete strain Streptomyces sp. HDN155000. Three flavoprotein monooxygenases are confirmed to be responsible for the oxidative carbon skeleton rearrangements in the biosynthesis of compounds 1 and 2. The obtained compounds showed promising cytotoxicity against different types of cancer cells.

AB - Six new angucycline structures, including spirocyclione A (1), which contains an unusual oxaspiro[5.5]undecane architecture, and its ring-A-cleaved product spirocyclione B (2), were discovered by heterologous expression of a type II polyketide biosynthetic gene cluster captured from a marine actinomycete strain Streptomyces sp. HDN155000. Three flavoprotein monooxygenases are confirmed to be responsible for the oxidative carbon skeleton rearrangements in the biosynthesis of compounds 1 and 2. The obtained compounds showed promising cytotoxicity against different types of cancer cells.

UR - https://www.scopus.com/pages/publications/85202560402

U2 - 10.1021/acs.orglett.4c02074

DO - 10.1021/acs.orglett.4c02074

M3 - Article

C2 - 39194005

AN - SCOPUS:85202560402

SN - 1523-7060

VL - 26

SP - 7489

EP - 7494

JO - Organic Letters

JF - Organic Letters

IS - 36

ER -

Biosynthesis of Atypical Angucyclines Unveils New Ring Rearrangement Reactions Catalyzed by Flavoprotein Monooxygenases

Abstract

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