Citation: Yayue Wang, Haojie Yang, Jie Li, Qiao Kong, Siming Zhou, Hongbao Sun, Lili Pan, Qiyong Gong, Ping Feng, Haoxing Wu. A biocompatible Horner-Wadsworth-Emmons (HWE) reaction triggered by a bioorthogonal proximity-induced platform[J]. Chinese Chemical Letters, ;2024, 35(8): 109226. doi: 10.1016/j.cclet.2023.109226 shu

A biocompatible Horner-Wadsworth-Emmons (HWE) reaction triggered by a bioorthogonal proximity-induced platform

Yayue Wang ^{a, 1} ,
Haojie Yang ^{a, 1} ,
Jie Li ^a ,
Qiao Kong ^b ,
Siming Zhou ^b ,
Hongbao Sun ^a ,
Lili Pan ^c ,
Qiyong Gong ^{a, d} ,
Ping Feng ^{e, f, *,} ,
Haoxing Wu ^{a, b, *,}

a.
Department of Radiology and Huaxi MR Research Center (HMRRC), Functional and Molecular Imaging Key Laboratory of Sichuan Province, Frontiers Science Center for Disease Related Molecular Network, West China Hospital, Sichuan University, Chengdu 610041, China
b.
Key Laboratory of Drug-Targeting and Drug Delivery System of the Education Ministry and Sichuan Province, Sichuan University, Chengdu 610041, China
c.
Department of Nuclear Medicine, Laboratory of Clinical Nuclear Medicine, West China Hospital, Sichuan University, Chengdu 610041, China
d.
Reseacrch Unit of Psychoradiology, Chinese Academy of Medical Sciences, Chengdu 610041, China
e.
Department of Pharmacy, West China Hospital, Sichuan University, Chengdu 610041, China
f.
Clinical Trial Center and National Medical Products Administration Key Laboratory for Clinical Research and Evaluation of Innovative Drugs, West China Hospital, Sichuan University, Chengdu 610041, China

fengping@wchscu.cn

haoxingwu@scu.edu.cn

Received Date: 1 September 2023
Revised Date: 13 October 2023
Accepted Date: 17 October 2023
Available Online: 20 October 2023

Figures(5)

Here, we present a novel bioorthogonal platform that enables precise positioning of attached moieties in close proximity, thereby facilitating the discovery and optimization of biocompatible reactions. Using this platform, we achieve a Horner-Wadsworth-Emmons (HWE) reaction under physiological conditions, generating a fluorophore in situ with a yield of up to 93%. This proximity platform should facilitate the discovery of various types of biocompatible reactions, making it a versatile tool for biomedical applications.
- Biocompatible reactions,
- Horner-Wadsworth-Emmons reaction,
- Bioorthogonal reactions,
- Tetrazines,
- Proximity effects
1. [1]
  V. Rigolot, C. Biot, C. Lion, Angew. Chem. Int. Ed. 60 (2021) 23084-23105. doi: 10.1002/anie.202101502
2. [2]
  J.A. Prescher, C.R. Bertozzi, Nat. Chem. Biol. 1 (2005) 13-21. doi: 10.1038/nchembio0605-13
3. [3]
  D. Wu, K. Yang, Z. Zhang, et al., Chem. Soc. Rev. 51 (2022) 1336-1376. doi: 10.1039/d1cs00451d
4. [4]
  N.K. Devaraj, ACS Cent. Sci. 4 (2018) 952-959. doi: 10.1021/acscentsci.8b00251
5. [5]
  S.L. Scinto, D.A. Bilodeau, R. Hincapie, et al., Nat. Rev. Methods Primers 1 (2021) 30. doi: 10.1038/s43586-021-00028-z
6. [6]
  D.M. Patterson, L.A. Nazarova, J.A. Prescher, ACS Chem. Biol. 9 (2014) 592-605. doi: 10.1021/cb400828a
7. [7]
  J. Wang, X. Wang, X. Fan, P.R. Chen, ACS Cent. Sci. 7 (2021) 929-943. doi: 10.1021/acscentsci.1c00124
8. [8]
  E. Kim, H. Koo, Chem. Sci. 10 (2019) 7835-7851. doi: 10.1039/c9sc03368h
9. [9]
  I. Novianti, T. Kowada, S. Mizukami, Org. Lett. 24 (2022) 3223-3226. doi: 10.1021/acs.orglett.2c01010
10. [10]
  T.K. Heiss, R.S. Dorn, J.A. Prescher, Chem. Rev. 121 (2021) 6802-6849. doi: 10.1021/acs.chemrev.1c00014
11. [11]
  E.M. Sletten, C.R. Bertozzi, Acc. Chem. Res. 44 (2011) 666-676. doi: 10.1021/ar200148z
12. [12]
  B.L. Oliveira, Z. Guo, G.J.L. Bernardes, Chem. Soc. Rev. 46 (2017) 4895-4950. doi: 10.1039/C7CS00184C
13. [13]
  H. Wu, N.K. Devaraj, Top. Curr. Chem. 374 (2015) 3. doi: 10.1201/b18327-3
14. [14]
  G.S. Kumar, Q. Lin, Chem. Rev. 121 (2021) 6991-7031. doi: 10.1021/acs.chemrev.0c00799
15. [15]
  R.K.V. Lim, Q. Lin, Acc. Chem. Res. 44 (2011) 828-839. doi: 10.1021/ar200021p
16. [16]
  J. Li, H. Kong, C. Zhu, Y. Zhang, Chem. Sci. 11 (2020) 3390-3396. doi: 10.1039/c9sc06540g
17. [17]
  O. Seitz, J. Pept. Sci. 25 (2019) e3198. doi: 10.1002/psc.3198
18. [18]
  A.Osuna Gálvez, J.W. Bode, J. Am. Chem. Soc. 141 (2019) 8721-8726. doi: 10.1021/jacs.9b03597
19. [19]
  X. Li, D.R. Liu, Angew. Chem. Int. Ed. 43 (2004) 4848-4870. doi: 10.1002/anie.200400656
20. [20]
  Y. Huang, Y. Li, X. Li, Nat. Chem. 14 (2022) 129-140. doi: 10.1038/s41557-021-00877-x
21. [21]
  G. Li, Y. Liu, Y. Liu, et al., Angew. Chem. Int. Ed. 52 (2013) 9544-9549. doi: 10.1002/anie.201302161
22. [22]
  P. Zhao, Z. Chen, Y. Li, et al., Angew. Chem. Int. Ed. 53 (2014) 10056-10059. doi: 10.1002/anie.201404830
23. [23]
  B.Z. Stanton, E.J. Chory, G.R. Crabtree, Science 359 (2018) eaao5902. doi: 10.1126/science.aao5902
24. [24]
  T.W. Corson, N. Aberle, C.M. Crews, ACS Chem. Biol. 3 (2008) 677-692. doi: 10.1021/cb8001792
25. [25]
  M.J.C. Long, J.R. Poganik, Y. Aye, J. Am. Chem. Soc. 138 (2016) 3610-3622. doi: 10.1021/jacs.5b12608
26. [26]
  S. Kolodych, E. Rasolofonjatovo, M. Chaumontet, et al., Angew. Chem. Int. Ed. 52 (2013) 12056-12060. doi: 10.1002/anie.201305645
27. [27]
  C.L. Schreiber, B.D. Smith, Nat. Rev. Chem. 3 (2019) 393-400. doi: 10.1038/s41570-019-0095-1
28. [28]
  W. Mao, W. Shi, J. Li, et al., Angew. Chem. Int. Ed. 58 (2019) 1106-1109. doi: 10.1002/anie.201812550
29. [29]
  Y. Xie, Y. Fang, Z. Huang, et al., Angew. Chem. Int. Ed. 59 (2020) 16967-16973. doi: 10.1002/anie.202005569
30. [30]
  Z.S. Alghamdi, M. Klausen, A. Gambardella, A. Lilienkampf, M. Bradley, Org. Lett. 25 (2023) 3104-3108. doi: 10.1021/acs.orglett.3c00955
31. [31]
  P. Brandt, P.O. Norrby, I. Martin, T. Rein, J. Org. Chem. 63 (1998) 1280-1289. doi: 10.1021/jo971973t
32. [32]
  R.O. Larsen, G. Aksnes, Phosphorus Sulf. Relat. Elem. 15 (1983) 219-228. doi: 10.1080/03086648308073297
33. [33]
  S.S. Nguyen, J.A. Prescher, Nat. Rev. Chem. 4 (2020) 476-489. doi: 10.1038/s41570-020-0205-0
34. [34]
  C.P. Ramil, M. Dong, P. An, et al., J. Am. Chem. Soc. 139 (2017) 13376-13386. doi: 10.1021/jacs.7b05674
35. [35]
  D.K. Kölmel, E.T. Kool, Chem. Rev. 117 (2017) 10358-10376. doi: 10.1021/acs.chemrev.7b00090
36. [36]
  W. Mao, J. Tang, L. Dai, et al., Angew. Chem. Int. Ed. 60 (2021) 2393-2397. doi: 10.1002/anie.202011544
37. [37]
  T.K. Heiss, R.S. Dorn, A.J. Ferreira, A.C. Love, J.A. Prescher, J. Am. Chem. Soc. 144 (2022) 7871-7880. doi: 10.1021/jacs.2c02058
38. [38]
  Z. Shao, C. Zhang, X. Zhu, et al., Chin. Chem. Lett. 30 (2019) 2169-2172. doi: 10.1016/j.cclet.2019.06.023
39. [39]
  X. Li, H. Yang, Y. Teng, et al., Chin. Chem. Lett. 33 (2022) 4223-4228. doi: 10.1016/j.cclet.2022.03.008
40. [40]
  N. Ahmed, W. Zareen, Y. Ye, Chin. Chem. Lett. 33 (2022) 2765-2772. doi: 10.1016/j.cclet.2021.12.092
41. [41]
  W. Liu, J. Chen, Q. Qiao, X. Liu, Z. Xu, Chin. Chem. Lett. 33 (2022) 4943-4947. doi: 10.1016/j.cclet.2022.03.121
42. [42]
  S. He, S. Zhang, X. Zhao, et al., Chin. Chem. Lett. 33 (2022) 4233-4237. doi: 10.1016/j.cclet.2022.02.020
43. [43]
  Z. Cao, D. Wu, M. Li, et al., Chin. Chem. Lett. 33 (2022) 1533-1536. doi: 10.1016/j.cclet.2021.09.001
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