Carrier Protein Mediated Formation of the Dihydropyridazinone Ring in Actinopyridazinone Biosynthesis.
Biosynthesis
Enzymes
Heterocycles
Natural Product
N−N Bond Formation
Journal
Angewandte Chemie (International ed. in English)
ISSN: 1521-3773
Titre abrégé: Angew Chem Int Ed Engl
Pays: Germany
ID NLM: 0370543
Informations de publication
Date de publication:
17 07 2023
17 07 2023
Historique:
received:
12
04
2023
medline:
12
7
2023
pubmed:
17
5
2023
entrez:
17
5
2023
Statut:
ppublish
Résumé
Heterocycles with nitrogen-nitrogen (N-N) bonds are privileged building blocks of synthetic drugs. They are also found in natural products, although the biosynthetic logic behind them is poorly understood. Actinopyridazinones produced by Streptomyces sp. MSD090630SC-05 possess unique dihydropyridazinone rings that have been studied as core nuclei in several approved synthetic therapeutics. Herein, we performed gene knockouts and in vitro biochemical experiments to elucidate the major steps in actinopyridazinone biosynthesis, including the unprecedented carrier protein mediated machinery for dihydropyridazinone formation.
Identifiants
pubmed: 37194491
doi: 10.1002/anie.202305155
doi:
Substances chimiques
Carrier Proteins
0
Biological Products
0
Nitrogen
N762921K75
Types de publication
Journal Article
Research Support, Non-U.S. Gov't
Langues
eng
Sous-ensembles de citation
IM
Pagination
e202305155Informations de copyright
© 2023 Wiley-VCH GmbH.
Références
M. F. Khan, M. M. Alam, G. Verma, W. Akhtar, M. Akhter, M. Shaquiquzzaman, Eur. J. Med. Chem. 2016, 120, 170-201.
K. Bozorov, J. Zhao, H. A. Aisa, Bioorg. Med. Chem. 2019, 27, 3511-3531;
R. Aggarwal, G. Sumran, Eur. J. Med. Chem. 2020, 205, 112652.
C. G. Neochoritis, T. Zhao, A. Dömling, Chem. Rev. 2019, 119, 1970-2042.
C. G. Wermuth, MedChemComm 2011, 2, 935-941;
Z. X. He, Y. P. Gong, X. Zhang, L. Y. Ma, W. Zhao, Eur. J. Med. Chem. 2021, 209, 112946.
S. Dubey, P. A. Bhosle, Med. Chem. Res. 2015, 24, 3579-3598;
W. Akhtar, M. Shaquiquzzaman, M. Akhter, G. Verma, M. F. Khan, M. M. Alam, Eur. J. Med. Chem. 2016, 123, 256-281.
L. M. Blair, J. Sperry, J. Nat. Prod. 2013, 76, 794-812.
G. Le Goff, J. Ouazzani, Bioorg. Med. Chem. 2014, 22, 6529-6544.
L. Chen, Z. Deng, C. Zhao, ACS Chem. Biol. 2021, 16, 559-570.
H. Y. He, H. Niikura, Y. L. Du, K. S. Ryan, Chem. Soc. Rev. 2022, 51, 2991-3046.
Y. Katsuyama, K. Matsuda, Curr. Opin. Chem. Biol. 2020, 59, 62-68.
A. J. Waldman, T. L. Ng, P. Wang, E. P. Balskus, Chem. Rev. 2017, 117, 5784-5863.
K. Matsuda, T. Tomita, K. Shin-ya, T. Wakimoto, T. Kuzuyama, M. Nishiyama, J. Am. Chem. Soc. 2018, 140, 9083-9086.
A. Del Rio Flores, F. F. Twigg, Y. Du, W. Cai, D. Q. Aguirre, M. Sato, M. J. Dror, M. Narayanamoorthy, J. Geng, N. A. Zill, R. Zhai, W. Zhang, Nat. Chem. Biol. 2021, 17, 1305-1313.
G. Zhao, W. Peng, K. Song, J. Shi, X. Lu, B. Wang, Y. L. Du, Nat. Commun. 2021, 12, 7205.
K. Matsuda, F. Hasebe, Y. Shiwa, Y. Kanesaki, T. Tomita, H. Yoshikawa, K. Shin-ya, T. Kuzuyama, M. Nishiyama, ACS Chem. Biol. 2017, 12, 124-131.
F. F. Twigg, W. Cai, W. Huang, J. Liu, M. Sato, T. J. Perez, J. Geng, M. J. Dror, I. Montanez, T. L. Tong, H. Lee, W. Zhang, ChemBioChem 2019, 20, 1145-1149.
S. A. Wang, Y. Ko, J. Zeng, Y. Geng, D. Ren, Y. Ogasawara, S. Irani, Y. Zhang, H. W. Liu, J. Am. Chem. Soc. 2019, 141, 6127-6131.
D. Ren, S. A. Wang, Y. Ko, Y. Geng, Y. Ogasawara, H. W. Liu, Angew. Chem. Int. Ed. 2019, 58, 16512-16516.
G. Zhao, S. Yao, K. W. Rothchild, T. Liu, Y. Liu, J. Lian, H. Y. He, K. S. Ryan, Y. L. Du, ChemBioChem 2020, 21, 644-649.
M. Zhang, P. Zhang, G. Xu, W. Zhou, Y. Gao, R. Gong, Y. S. Cai, H. Cong, Z. Deng, N. P. J. Price, X. Mao, W. Chen, Appl. Environ. Microbiol. 2020, 86, e01971-19.
K. Matsuda, K. Arima, S. Akiyama, Y. Yamada, Y. Abe, H. Suenaga, J. Hashimoto, K. Shin-ya, M. Nishiyama, T. Wakimoto, J. Am. Chem. Soc. 2022, 144, 12954-12960.
Z. C. Wang, I. W. Lo, K. H. Lin, A. N. Cheng, S. M. Zadeh, Y. H. Huang, T. L. Li, Appl. Environ. Microbiol. 2022, 88, e0080622.
W. She, W. Ye, A. Cheng, X. Liu, J. Tang, Y. Lan, F. Chen, P. Y. Qian, Front. Microbiol. 2021, 12, 635268.
B. T. Weinert, V. Iesmantavicius, S. A. Wagner, C. Schölz, B. Gummesson, P. Beli, T. Nyström, C. Choudhary, Mol. Cell 2013, 51, 265-272.
Y. L. Du, H. Y. He, M. A. Higgins, K. S. Ryan, Nat. Chem. Biol. 2017, 13, 836-838.
G. Zhao, Y. Y. Guo, S. Yao, X. Shi, L. Lv, Y. L. Du, Nat. Commun. 2020, 11, 1614.
F. Hou, Y. Wan, Q. Gan, M. Xian, W. Huang, Front. Bioeng. Biotechnol. 2020, 8, 603514.
A. Ito, J. H. Choi, W. Yokoyama-Maruyama, M. Kotajima, J. Wu, T. Suzuki, Y. Terashima, H. Suzuki, H. Hirai, D. C. Nelson, Y. Tsunematsu, K. Watanabe, T. Asakawa, H. Ouchi, M. Inai, H. Dohra, H. Kawagishi, Org. Biomol. Chem. 2022, 20, 2636-2642.
K. Song, W. Li, Z. Zhao, H. Li, Y. Liu, G. Zhao, H. Y. He, Y. L. Du, Org. Lett. 2023, 25, 2918-2922.
J. M. Winter, A. L. Jansma, T. M. Handel, B. S. Moore, Angew. Chem. Int. Ed. 2009, 48, 767-770.
O. Yahiaoui, L. A. M. Murray, F. Zhao, B. S. Moore, K. N. Houk, F. Liu, J. H. George, Org. Lett. 2022, 24, 490-495.