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Synlett 2024; 35(05): 552-564
DOI: 10.1055/a-2043-4479
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Biomimetic Synthesis

New Paradigms in Catalysis Inspired by Cytochromes P450

Yanqun Gao‡
a   Jiangsu Key Laboratory of Biofunctional Materials, Jiangsu Collaborative Innovation Center of Biomedical Functional Materials, Key Laboratory of Applied Photochemistry, School of Chemistry and Materials Science, Nanjing Normal University, Wenyuan Road NO.1, Nanjing 210023, P. R. of China
,
Lu Cheng‡
a   Jiangsu Key Laboratory of Biofunctional Materials, Jiangsu Collaborative Innovation Center of Biomedical Functional Materials, Key Laboratory of Applied Photochemistry, School of Chemistry and Materials Science, Nanjing Normal University, Wenyuan Road NO.1, Nanjing 210023, P. R. of China
,
Wei Shi
b   Hunan Engineering Research Center for Recycled Aluminum, College of Chemistry & Materials Engineering, Huaihua University, Huaihua 418008, P. R. of China
,
Yuejun Ouyang
b   Hunan Engineering Research Center for Recycled Aluminum, College of Chemistry & Materials Engineering, Huaihua University, Huaihua 418008, P. R. of China
,
Wei Han  ∗
a   Jiangsu Key Laboratory of Biofunctional Materials, Jiangsu Collaborative Innovation Center of Biomedical Functional Materials, Key Laboratory of Applied Photochemistry, School of Chemistry and Materials Science, Nanjing Normal University, Wenyuan Road NO.1, Nanjing 210023, P. R. of China
› Author AffiliationsThis work was sponsored by the Natural Science Foundation of Hunan Province (2020JJ4487 and 2021JJ40431), the Natural Science Foundation of China (21776139), the ‘Qing Lan Project’ Young and Middle-Aged Academic Leaders of Jiangsu Provincial Colleges and Universities, and the Priority Academic Program Development of Jiangsu Higher Education Institutions.
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Abstract

Cytochromes P450 (P450s or CYPs) are versatile biocatalysts capable of realizing a broad range of synthetically challenging reactions. The development of synthetic catalysts/catalytic systems that model enzyme functions is a goal that has long been pursued. In this account, we mainly summarize our latest advances in the field of catalysis inspired by cytochromes P450, including reductive activation strategies for highly efficient oxidations and an unusual l-cystine-derived ligand as a model of P450s for highly efficient iron-catalyzed undirected arene C–H hydroxylation. These new paradigms highlight some of the catalytic properties of P450s, such as effective late-stage functionalization of complex targets, good reactive functional group tolerance, and high catalytic efficiency and selectivity.

1 Introduction

2 Reductive Activation Strategies for Oxygenation

3 An Fe/Cysteine-Based Ligand as a Biomimetic Model of Cytochromes P450 for Arene C–H Hydroxylation

4 Conclusion

Key words

cytochromes P450 - bio-inspired catalysis - iron catalysis - oxidation - late-stage functionalization - reductive activation strategy - I-cystine-derived ligand


Publication History

Received: 30 December 2022

Accepted after revision: 27 February 2023

Accepted Manuscript online:
27 February 2023

Article published online:
27 March 2023

© 2023. Thieme. All rights reserved

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  • References

    • 2a de Montellano PR. O. Cytochrome P450: Structure, Mechanism and Biochemistry, 3rd ed. Kluwer Academic/Plenum Publishers; New York: 2005
      CrossrefGoogle Scholar
    • 2b Coon MJ. Annu. Rev. Pharmacol. Toxicol. 2004; 45: 1
      CrossrefPubMed
    • 2c Zanger UM, Schwab M. Pharmacol. Ther. 2013; 138: 103
      CrossrefPubMed
  • 3 Guengerich FP. ACS Catal. 2018; 8: 10964
    CrossrefPubMed
    • 4a Urlacher VB, Girhard M. Trends Biotechnol. 2019; 37: 882
      CrossrefPubMed
    • 4b Kelly SL, Kelly DE. Phil. Trans. R. Soc. B 2013; 368: 20120476
      CrossrefPubMed
  • 5 Nardo GD, Gilardi G. Trends Biochem. Sci. 2020; 45: 511
    CrossrefPubMed
    • 6a Dong J, Fernández-Fueyo E, Hollmann F, Paul CE, Pesic M, Schmidt S, Wang Y, Younes S, Zhang W. Angew. Chem. Int. Ed. 2018; 57: 9238
      CrossrefPubMed
    • 6b O’Reilly E, Köhler V, Flitsch SL, Turner NJ. Chem. Commun. 2011; 47: 2490
      CrossrefPubMed
  • 7 Groves JT, Nemo TE, Myers RS. J. Am. Chem. Soc. 1979; 101: 1032
    CrossrefPubMed
    • 8a Mansuy D. C. R. Chim. 2007; 10: 392
      Crossref
    • 8b Kadish KM, Smith KM, Guilard R. The Porphyrin Handbook . Academic Press; San Diego: 2000
      Google Scholar
    • 8c Che CM, Huang JS. Chem. Commun. 2009; 3996
      CrossrefPubMed
    • 8d Lu HJ, Peter X. Chem. Soc. Rev. 2011; 40: 1899
      CrossrefPubMed
    • 8e Metalloporphyrins in Catalytic Oxidations . Sheldon RA. Marcel Dekker;   New York: 1994
      Google Scholar
    • 8f Costas M. Coord. Chem. Rev. 2011; 255: 2912
      Crossref
    • 8g Regina A, Baglia JP, Zaragoza T, David PG. Chem. Rev. 2017; 117: 13320
      CrossrefPubMed
    • 8h Mariette M, Pereira LD, Dias M, Calvete JF. ACS Catal. 2018; 8: 10784
      Crossref
    • 8i Alexander B. Chem. Rev. 2013; 113: 8152
      CrossrefPubMed
    • 8j Che CM, Lo VK. Y, Zhou CY, Huang JS. Chem. Soc. Rev. 2011; 40: 1950
      CrossrefPubMed
    • 8k Huang X, Bergsten TM, Groves JT. J. Am. Chem. Soc. 2015; 137: 5300
      CrossrefPubMed
    • 8l Liu W, Groves JT. J. Am. Chem. Soc. 2010; 132: 12847
      CrossrefPubMed
    • 8m Liu W, Huang X, Cheng M.-J, Nielsen RJ, Goddard WA. III, Groves JT. Science 2012; 337: 1322
      CrossrefPubMed
  • 9 Huang XY, Groves JT. Chem. Rev. 2018; 118: 2491
    CrossrefPubMed
    • 10a Vatsis PK, Peng H.-M, Coon JM. J. Inorg. Biochem. 2002; 91: 542
      CrossrefPubMed
    • 10b Yosca TH, Ledray AP, Ngo J, Green MT. J. Biol. Inorg. Chem. 2017; 22: 209
      CrossrefPubMed
    • 11a Barton DH. R, Doller D. Acc. Chem. Res. 1992; 25: 504
      Crossref
    • 11b Barton DH. R, Halley F, Ozbalik N, Schmitt M, Young E, Balavoine G. J. Am. Chem. Soc. 1989; 111: 7144
      Crossref
    • 11c Barton DH. R, Gastiger MJ, Motherwell WB. J Chem. Soc. 1983; 41
      Crossref
  • 12 Singh B, Long JR, Biani FF, Gatteschi D, Stavropoulos P. J. Am. Chem. Soc. 1997; 119: 7030
    CrossrefPubMed
  • 13 Punniyamurthy T, Velusamy S, Iqbal J. Chem. Rev. 2005; 105: 2329
    CrossrefPubMed
    • 15a Gui J, Pan CM, Jin Y, Qin T, Lo JC, Lee BJ. Spergel S. H, Mertzman ME, Pitts WJ, La Cruz TE, Schmidt MA, Darvatkar N, Natarajan SR, Baran PS. Science 2015; 348: 886
      CrossrefPubMed
    • 15b Lo JC, Gui J, Yabe Y, Pan CM, Baran PS. Nature 2014; 516: 343
      CrossrefPubMed
    • 15c Lo JC, Kim DY, Pan CM, Edwards JT, Yabe Y, Gui JH, Qin T, Gutirrez S, Giacoboni J, Smith MW, Holland PL, Baran PS. J. Am. Chem. Soc. 2017; 139: 2484
      CrossrefPubMed
    • 15d Lo JC, Yabe Y, Baran PS. J. Am. Chem. Soc. 2014; 136: 1304
      CrossrefPubMed
    • 15e Dao HT, Li C, Michaudel Q, Maxwell BD, Baran PS. J. Am. Chem. Soc. 2015; 137: 8046
      CrossrefPubMed
    • 16a Crossley SW. M, Obradors C, Martinez RM, Shenvi RA. Chem. Rev. 2016; 116: 8912
      CrossrefPubMed
    • 16b Hashimoto T, Hirose D, Taniguchi T. Angew. Chem. Int. Ed. 2014; 53: 2730
      CrossrefPubMed
    • 16c Leggans EK, Barker TJ, Duncan KK, Boger DL. Org. Lett. 2012; 21: 1428
      CrossrefPubMed
    • 16d Taniguchi T, Goto N, Nishibata A, Ishibashi H. Org. Lett. 2010; 12: 112
      CrossrefPubMed
    • 16e Sugimori T, Horike SI, Tsumura S, Handa M, Kasuga K. Inorg. Chim. Acta 1998; 283: 275
      Crossref
    • 16f Takeuchi M, Kodera M, Kano K, Yoshida Z. J. Mol. Catal. A: Chem. 1996; 113: 51
      Crossref
  • 18 DeLuca RJ, Edwards JL, Steffens LD, Michel BW, Qiao X, Zhu C, Cook SP, Sigman MS. J. Org. Chem. 2013; 78: 1682
    CrossrefPubMed
  • 19 Mitsudome T, Yoshida S, Mizugaki T, Jitsukawa K, Kaneda K. Angew. Chem. Int. Ed. 2013; 52: 5961
    CrossrefPubMed
  • 20 Kim E, Gordon DM, Schmid W, Whitesides GM. J. Org. Chem. 1993; 58: 5500
    CrossrefPubMed
  • 21 Yan JL, Cheng Y, Chen J, Ratnayake R, Dang LH, Luesch H, Guo Y, Ye T. Org. Lett. 2018; 20: 6170
    CrossrefPubMed
  • 22 Shi L, He Y, Gong J, Yang Z. Chem. Commun. 2020; 56: 531
    CrossrefPubMed
  • 23 Jackson RK. III, Wood JL. Org. Lett. 2021; 23: 1243
    CrossrefPubMed
  • 24 Puls F, Knölker HJ. Angew. Chem. Int. Ed. 2018; 57: 1222
    CrossrefPubMed
  • 25 Puls F, Linke P, Kataeva O, Knölker HJ. Angew. Chem. Int. Ed. 2021; 60: 14083
    CrossrefPubMed
  • 26 Hashimoto T, Maruyama T, Ishimaru T, Matsugaki M, Shiota K, Yamaguchi Y. ChemistrySelect 2021; 6: 5534
    CrossrefPubMed
  • 27 Hammer SC, Kubik G, Watkins E, Huang S, Minges H, Arnold FH. Science 2017; 358: 215
    CrossrefPubMed
    • 28a Vasseur A, Brufaerts J, Marek I. Nat. Chem. 2016; 8: 209
      CrossrefPubMed
    • 28b Sommer H, Juliá-Hernández F, Martin R, Marek I. ACS Cent. Sci. 2018; 4: 153
      CrossrefPubMed
  • 29 Liu B, Hu P, Xu F, Cheng L, Tan M, Han W. Commun. Chem. 2019; 2: 5
    CrossrefPubMed
  • 30 Gong PX, Xu F, Cheng L, Gong X, Zhang J, Gu W.-J, Han W. Chem. Commun. 2021; 57: 5905
    CrossrefPubMed
    • 31a Crabtree RH. Chem. Rev. 1985; 85: 245
      Crossref
    • 31b Kim DS, Park WJ, Jun CH. Chem. Rev. 2017; 117: 8977
      CrossrefPubMed
  • 32 Liu J, Wen X, Qin C, Li X, Luo X, Sun A, Zhu B, Song S, Jiao N. Angew. Chem. Int. Ed. 2017; 56: 11940
    CrossrefPubMed
  • 33 Gonzalez-de-Castro A, Xiao J. J. Am. Chem. Soc. 2015; 137: 8206
    CrossrefPubMed
  • 34 Liu B, Cheng L, Hu P, Xu F, Li D, Gu W.-J, Han W. Chem. Commun. 2019; 55: 4817
    CrossrefPubMed
  • 35 Collins TJ, Ryabov AD. Chem. Rev. 2017; 117: 9140
    CrossrefPubMed
  • 36 Hu PH, Tang MX, Cheng L, Zhao HY, Gu W.-J, Han W. Nat. Commun. 2019; 10: 2425
    CrossrefPubMed
    • 37a Wang M.-K, Zhou Z, Tang R.-Y, Zhang X.-G, Deng C. Synlett 2013; 24: 737
      Article in Thieme Connect
    • 37b Durán-Peña MJ, Botubol-Ares MJ, Hanson JR, Hernández-Galán R, Collado IG. Eur. J. Org. Chem. 2015; 6333
      Crossref
  • 38 Han W, Cheng L, Zhao H. Synlett 2020; 31: 1400
    Article in Thieme ConnectPubMed
  • 39 Cheng L, Wang H, Cai H, Zhang J, Gong X, Han W. Science 2021; 374: 77
    CrossrefPubMed
  • 40 Dey A, Jiang Y, de Montellano PO, Hodgson KO, Hedman B, Solomon EI. J. Am. Chem. Soc. 2009; 131: 7869
    CrossrefPubMed
  • 41 Yosca TH, Rittle J, Krest CM, Onderko EL, Silakov A, Calixto JC, Behan RK, Green MT. Science 2013; 342: 825
    CrossrefPubMed