Citation: Wenling Yuan, Fengli Li, Zhe Chen, Qiaoxin Xu, Zhenhua Guan, Nanyu Yao, Zhengxi Hu, Junjun Liu, Yuan Zhou, Ying Ye, Yonghui Zhang. AbnI: An α-ketoglutarate-dependent dioxygenase involved in brassicicene CH functionalization and ring system rearrangement[J]. Chinese Chemical Letters, ;2024, 35(5): 108788. doi: 10.1016/j.cclet.2023.108788 shu

AbnI: An α-ketoglutarate-dependent dioxygenase involved in brassicicene CH functionalization and ring system rearrangement

Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, China

ying_ye@hust.edu.cn

zhangyh@mails.tjmu.edu.cn

Received Date: 24 May 2023
Revised Date: 3 July 2023
Accepted Date: 5 July 2023
Available Online: 7 July 2023

Figures(6)

We reported the characterization of a novel brassicicene diterpene biosynthetic gene cluster, which contains a unique α-ketoglutarate-dependent dioxygenase (αKGD) enzyme, AbnI. Our findings revealed that AbnI demonstrates remarkable substrate promiscuity and is capable of activating multiple sites on both 5–8–5 and 5–9–5 brassicicene skeletons, resulting in skeleton modifications and an unexpected ring system rearrangement. These results suggested the potential utility of AbnI as an enzymatic tool for terpene CH functionalization. In addition, the catalytic mechanism of AbnI and its potential ecological implications were discussed.
- Fungal diterpenes,
- α-Ketoglutarate-dependent dioxygenase,
- C-H functionalization,
- Rearrangement,
- Brassicicenes
1. [1]
  Q. Li, M. Zhang, X. Zhang, et al., Chin. Chem. Lett. 35 (2024) 108193. doi: 10.1016/j.cclet.2023.108193
2. [2]
  Z.W. Tong, T.T. Wang, P. Yang, et al., Chin. Chem. Lett. 35 (2024) 108488. doi: 10.1016/j.cclet.2023.108488
3. [3]
  A. Rokas, M.E. Mead, J.L. Steenwyk, H.A. Raja, N.H. Oberlies, Nat. Prod. Rep. 37 (2020) 868–878. doi: 10.1039/c9np00045c
4. [4]
  L.M. Podust, D.H. Sherman, Nat. Prod. Rep. 29 (2012) 1251–1266. doi: 10.1039/c2np20020a
5. [5]
  M. Ferrara, A. Gallo, G. Perrone, D. Magista, S.E. Baker, Front. Microbiol. 11 (2020) 581309. doi: 10.3389/fmicb.2020.581309
6. [6]
  U. Galm, E. Wendt-Pienkowski, L. Wang, et al., J. Nat. Prod. 74 (2011) 526–536. doi: 10.1021/np1008152
7. [7]
  M.C. Tang, X. Cui, X. He, et al., Org. Lett. 19 (2017) 5376–5379. doi: 10.1021/acs.orglett.7b02653
8. [8]
  M. Nowakowska, M. Wrzesińska, P. Kamiński, et al., Eur. J. Plant Pathol. 153 (2018) 131–151.
9. [9]
  Y. Ono, A. Minami, M. Noike, et al., J. Am. Chem. Soc. 133 (2011) 2548–2555. doi: 10.1021/ja107785u
10. [10]
  Y. Tang, Y. Xue, G. Du, et al., Angew. Chem. Int. Ed. 55 (2016) 4069–4073. doi: 10.1002/anie.201600313
11. [11]
  A. Tazawa, Y. Ye, T. Ozaki, et al., Org. Lett. 20 (2018) 6178–6182. doi: 10.1021/acs.orglett.8b02654
12. [12]
  F. Li, W. Sun, J. Guan, et al., Org. Biomol. Chem. 16 (2018) 8751–8760. doi: 10.1039/c8ob02353k
13. [13]
  F. Li, L. Pan, S. Lin, et al., Bioorg. Chem. 100 (2020) 103887. doi: 10.1016/j.bioorg.2020.103887
14. [14]
  F. Li, S. Lin, S. Zhang, et al., J. Nat. Prod. 83 (2020) 1931–1938. doi: 10.1021/acs.jnatprod.0c00165
15. [15]
  F. Li, S. Lin, S. Zhang, et al., Org. Lett. 21 (2019) 8353–8357. doi: 10.1021/acs.orglett.9b03133
16. [16]
  A. Bhattacharya, S. Kourmpetli, D.A. Ward, et al., Plant Physiol. 160 (2012) 837–845. doi: 10.1104/pp.112.201756
17. [17]
  T. Paysan-Lafosse, M. Blum, S. Chuguransky, et al., Nucleic Acids Res. 51 (2023) D418–D427. doi: 10.1093/nar/gkac993
18. [18]
  T. Mori, R. Zhai, R. Ushimaru, Y. Matsuda, I. Abe, Nat. Commun. 12 (2021) 4417. doi: 10.1038/s41467-021-24685-6
19. [19]
  X. Liu, Z. Yuan, H. Su, et al., ACS Catal. 12 (2022) 3689–3699. doi: 10.1021/acscatal.1c04627
20. [20]
  T. Mori, I. Abe, Beilstein J. Org. Chem. 18 (2022) 707–721. doi: 10.3762/bjoc.18.71
21. [21]
  C.A. Rouzer, L.J. Marnett, J. Lipid Res. 50 (Suppl) (2009) S29–S34.
22. [22]
  N.P. Dunham, J.M. Del Rio Pantoja, B. Zhang, et al., J. Am. Chem. Soc. 141 (2019) 9964–9979. doi: 10.1021/jacs.9b03567
23. [23]
  L. Wu, Z. Wang, Y. Cen, B. Wang, J. Zhou, Angew. Chem. Int. Ed. 61 (2022) e202112063. doi: 10.1002/anie.202112063
24. [24]
  Z. Hu, W. Sun, F. Li, et al., Org. Lett. 20 (2018) 5198–5202. doi: 10.1021/acs.orglett.8b02137
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2. [2]
  Peng Guo , Shicheng Dong , Xiang-Gui Zhang , Bing-Bin Yang , Jun Zhu , Ke-Yin Ye . Cobalt-catalyzed migratory carbon-carbon cross-coupling of borabicyclo[3.3.1]nonane (9-BBN) borates. Chinese Chemical Letters, 2025, 36(4): 110052-. doi: 10.1016/j.cclet.2024.110052
3. [3]
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4. [4]
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7. [7]
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9. [9]
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10. [10]
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11. [11]
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12. [12]
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13. [13]
  Chonglong He , Yulong Wang , Quan-Xin Li , Zichen Yan , Keyuan Zhang , Shao-Fei Ni , Xin-Hua Duan , Le Liu . Alkylarylation of alkenes with arylsulfonylacetate as bifunctional reagent via photoredox radical addition/Smiles rearrangement cascade. Chinese Chemical Letters, 2025, 36(5): 110253-. doi: 10.1016/j.cclet.2024.110253
14. [14]
  Jian Han , Li-Li Zeng , Qin-Yu Fei , Yan-Xiang Ge , Rong-Hui Huang , Fen-Er Chen . Recent advances in remote C(sp³)–H functionalization via chelating group-assisted metal-catalyzed chain-walking reaction. Chinese Chemical Letters, 2024, 35(11): 109647-. doi: 10.1016/j.cclet.2024.109647
15. [15]
  Tao Zhou , Jing Zhou , Yunyun Liu , Jie-Ping Wan , Fen-Er Chen . Transition metal-free tunable synthesis of 3-(trifluoromethylthio) and 3-trifluoromethylsulfinyl chromones via domino C–H functionalization and chromone annulation of enaminones. Chinese Chemical Letters, 2024, 35(11): 109683-. doi: 10.1016/j.cclet.2024.109683
16. [16]
  Yu Peng , Yue Wang , Tian-Jiao Chen , Jing-Jing Chen , Jin-Ling Yang , Ting Gong , Ping Zhu . A fungal CYP from Beauveria bassiana with promiscuous steroid hydroxylation capabilities. Chinese Chemical Letters, 2024, 35(5): 108818-. doi: 10.1016/j.cclet.2023.108818
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20. [20]
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