Citation: Guonan Ji, Xuetao Zheng, Xiangdie Hou, Xiao Sun, Shijie Wang, Xiaohong Li, Jianjun Cheng, Ziyuan Song. Modulation of polymerization rate of N-carboxyanhydrides in a biphasic system[J]. Chinese Chemical Letters, ;2024, 35(1): 108872. doi: 10.1016/j.cclet.2023.108872 shu

Modulation of polymerization rate of N-carboxyanhydrides in a biphasic system

Guonan Ji ^a ,
Xuetao Zheng ^c ,
Xiangdie Hou ^d ,
Xiao Sun ^a ,
Shijie Wang ^a ,
Xiaohong Li ^d ,
Jianjun Cheng ^{b, c} ,
Ziyuan Song ^{a, *,}

a.
Institute of Functional Nano & Soft Materials (FUNSOM), Jiangsu Key Laboratory for Carbon-Based Functional Materials and Devices, Soochow University, Suzhou 215123, China
b.
Research Center for Industries of the Future, Westlake University, Hangzhou 310030, China
c.
School of Engineering, Westlake University, Hangzhou 310030, China
d.
The Key Lab of Health Chemistry and Molecular Diagnosis of Suzhou, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou 215123, China

zysong@suda.edu.cn

Received Date: 1 June 2023
Revised Date: 29 July 2023
Accepted Date: 30 July 2023
Available Online: 1 August 2023

Figures(6)

The recent advances in accelerated polymerization of N-carboxyanhydrides (NCAs) offer an effective strategy to simplify the preparation of polypeptide materials. However, the fine-tuning of polymerization kinetics, which is critical to differentiate the main polymerization and the side reactions, remains largely unexplored. Herein we report the modulation of polymerization rate of NCA in a water/oil biphasic system. By altering the aqueous pH, the initial location of the initiators, and the pK_a of initiating amines, we observed the change in polymerization time from several minutes to a few hours. Due to the high interfacial activity and low pK_a value, controlled polymerization was observed from multi-amine initiators even if they were initially located in the aqueous phase. This work not only improves our understanding on the biphasic polymerization mechanism, but also facilitates preparation of versatile polypeptide materials.
- N-Carboxyanhydrides,
- Polypeptides,
- Biphasic system,
- Cooperative covalent polymerization,
- Polymerization kinetics
1. [1]
  T.J. Deming, Prog. Polym. Sci. 32 (2007) 858–875. doi: 10.1016/j.progpolymsci.2007.05.010
2. [2]
  K. Kataoka, A. Harada, Y. Nagasaki, Adv. Drug Deliv. Rev. 64 (2012) 37–48. doi: 10.1016/j.addr.2012.09.013
3. [3]
  C. He, X. Zhuang, Z. Tang, et al., Adv. Healthc. Mater. 1 (2012) 48–78. doi: 10.1002/adhm.201100008
4. [4]
  C. Deng, J. Wu, R. Cheng, et al., Prog. Polym. Sci. 39 (2014) 330–364. doi: 10.1016/j.progpolymsci.2013.10.008
5. [5]
  T.J. Deming, Chem. Rev. 116 (2016) 786–808. doi: 10.1021/acs.chemrev.5b00292
6. [6]
  Z. Song, Z. Han, S. Lv, et al., Chem. Soc. Rev. 46 (2017) 6570–6599. doi: 10.1039/C7CS00460E
7. [7]
  Z. Song, H. Fu, R. Wang, et al., Chem. Soc. Rev. 47 (2018) 7401–7425. doi: 10.1039/C8CS00095F
8. [8]
  Y. Liu, C.M. Dong, Chin. Chem. Lett. 28 (2017) 827–831. doi: 10.1016/j.cclet.2016.11.006
9. [9]
  X. Zhou, Z. Li, Adv. Healthc. Mater. 7 (2018) 1800020. doi: 10.1002/adhm.201800020
10. [10]
  A. Rasines Mazo, S. Allison-Logan, F. Karimi, et al., Chem. Soc. Rev. 49 (2020) 4737–4834. doi: 10.1039/C9CS00738E
11. [11]
  Y. Song, C.M. Dong, Chin. Chem. Lett. 33 (2022) 4084–4088. doi: 10.1016/j.cclet.2022.01.051
12. [12]
  T. Melnyk, S. Đorđević, I. Conejos-Sánchez, et al., Adv. Drug Deliv. Rev. 160 (2020) 136–169. doi: 10.1016/j.addr.2020.10.007
13. [13]
  T. Zhang, J. Yao, J. Tian, et al., Chin. Chem. Lett. 31 (2020) 1129–1132. doi: 10.1016/j.cclet.2019.07.010
14. [14]
  Y. Liu, L. Yin, Adv. Drug Deliv. Rev. 171 (2021) 139–163. doi: 10.1016/j.addr.2020.12.007
15. [15]
  Y. Jiang, Y. Chen, Z. Song, et al., Adv. Drug Deliv. Rev. 170 (2021) 261–280. doi: 10.1016/j.addr.2020.12.016
16. [16]
  P.D. Bartlett, R.H. Jones, J. Am. Chem. Soc. 79 (1957) 2153–2159. doi: 10.1021/ja01566a035
17. [17]
  T. Aliferis, H. Iatrou, N. Hadjichristidis, Biomacromolecules 5 (2004) 1653–1656. doi: 10.1021/bm0497217
18. [18]
  N. Hadjichristidis, H. Iatrou, M. Pitsikalis, et al., Chem. Rev. 109 (2009) 5528–5578. doi: 10.1021/cr900049t
19. [19]
  Y. Liu, D. Li, J. Ding, et al., Chin. Chem. Lett. 31 (2020) 3001–3014. doi: 10.1016/j.cclet.2020.04.029
20. [20]
  J. Zou, J. Fan, X. He, et al., Macromolecules 46 (2013) 4223–4226. doi: 10.1021/ma4007939
21. [21]
  R. Baumgartner, H. Fu, Z. Song, et al., Nat. Chem. 9 (2017) 614–622. doi: 10.1038/nchem.2712
22. [22]
  Y. Wu, D. Zhang, P. Ma, et al., Nat. Commun. 9 (2018) 5297. doi: 10.1038/s41467-018-07711-y
23. [23]
  J. Yuan, Y. Zhang, Z. Li, et al., ACS Macro Lett. 7 (2018) 892–897. doi: 10.1021/acsmacrolett.8b00465
24. [24]
  W. Zhao, Y. Lv, J. Li, et al., Nat. Commun. 10 (2019) 3590. doi: 10.1038/s41467-019-11524-y
25. [25]
  C. Chen, H. Fu, R. Baumgartner, et al., J. Am. Chem. Soc. 141 (2019) 8680–8683. doi: 10.1021/jacs.9b02298
26. [26]
  Z. Song, H. Fu, J. Wang, et al., Proc. Natl. Acad. Sci. U. S. A. 116 (2019) 10658–10663. doi: 10.1073/pnas.1901442116
27. [27]
  Z. Song, H. Fu, R. Baumgartner, et al., Nat. Commun. 10 (2019) 5470. doi: 10.1038/s41467-019-13502-w
28. [28]
  J. Jacobs, D. Pavlović, H. Prydderch, et al., J. Am. Chem. Soc. 141 (2019) 12522–12526. doi: 10.1021/jacs.9b06750
29. [29]
  S. Lv, H. Kim, Z. Song, et al., J. Am. Chem. Soc. 142 (2020) 8570–8574. doi: 10.1021/jacs.0c01173
30. [30]
  C. Grazon, P. Salas-Ambrosio, E. Ibarboure, et al., Angew. Chem. Int. Ed. 59 (2020) 622–626. doi: 10.1002/anie.201912028
31. [31]
  Y. Wu, K. Chen, X. Wu, et al., Angew. Chem. Int. Ed. 60 (2021) 26063–26071. doi: 10.1002/anie.202103540
32. [32]
  Y. Xia, Z. Song, Z. Tan, et al., Nat. Commun. 12 (2021) 732. doi: 10.1038/s41467-020-20724-w
33. [33]
  Y. Hu, Z.Y. Tian, W. Xiong, et al., Natl. Sci. Rev. 9 (2022) nwac033. doi: 10.1093/nsr/nwac033
34. [34]
  Y. Wu, M. Zhou, K. Chen, et al., Chin. Chem. Lett. 32 (2021) 1675–1678. doi: 10.1016/j.cclet.2021.02.039
35. [35]
  X. Wang, Z. Song, Z. Tan, et al., ACS Macro Lett. 8 (2019) 1517–1521. doi: 10.1021/acsmacrolett.9b00784
36. [36]
  T. Xue, Z. Song, Y. Wang, et al., Macromolecules 53 (2020) 6589–6597. doi: 10.1021/acs.macromol.0c00470
37. [37]
  W. Wang, H. Fu, Y. Lin, et al., Acc. Mater. Res. 4 (2023) 604–615. doi: 10.1021/accountsmr.3c00046
38. [38]
  E.R. Blout, M. Idelson, J. Am. Chem. Soc. 78 (1956) 3857–3858. doi: 10.1021/ja01596a083
39. [39]
  I. Dimitrov, H. Schlaad, Chem. Commun. 23 (2003) 2944–2945.
40. [40]
  E. Ellenbogen, J. Am. Chem. Soc. 74 (1952) 5198–5201. doi: 10.1021/ja01140a065
41. [41]
  C.D. Vacogne, H. Schlaad, Chem. Commun. 51 (2015) 15645–15648. doi: 10.1039/C5CC06905J
42. [42]
  L. Li, J. Cen, W. Pan, et al., Research 2021 (2021) 9826046.
43. [43]
  J. Coca, R.M. Diaz, C. Pazos, Fluid Phase Equilib. 4 (1980) 123–136. doi: 10.1016/0378-3812(80)80010-0
44. [44]
  B.M. Harvey, P.E. Hoggard, Monatsh. Chem. 143 (2012) 1101–1105. doi: 10.1007/s00706-012-0784-7
45. [45]
  D.D. Perrin, Dissociation Constants of Organic Bases in Aqueous solution, Supplement 1972, Butterworths, London, 1972.
46. [46]
  T. Zhang, P.R. Dvornic, S.N. Kaganove, Langmuir 23 (2007) 10589–10597. doi: 10.1021/la700457h
47. [47]
  D.A. Tomalia, A.M. Naylor, W.A. Goddard III, Angew. Chem. Int. Ed. 29 (1990) 138–175. doi: 10.1002/anie.199001381
48. [48]
  V.S. Bryantsev, M.S. Diallo, W.A. Goddard, J. Phys. Chem. A 111 (2007) 4422–4430. doi: 10.1021/jp071040t
49. [49]
  H. Collet, E. Souaid, H. Cottet, et al., Chem. Eur. J. 16 (2010) 2309–2316. doi: 10.1002/chem.200901734
50. [50]
  Y. Ge, P. Li, Y. Guan, et al., Chin. Chem. Lett. 30 (2019) 1428–1431. doi: 10.1016/j.cclet.2019.03.009
51. [51]
  H. Lu, J. Cheng, J. Am. Chem. Soc. 130 (2008) 12562–12563. doi: 10.1021/ja803304x
52. [52]
  F. Yang, Z. Liu, W. Si, et al., ACS Macro Lett. 11 (2022) 663–668. doi: 10.1021/acsmacrolett.2c00205
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