Citation: Liu Jingjing, Zhang Donghui, Jiang Weinan, Liu Runhui. Simple and Cost-Effective Synthesis of Fmoc-DOPA(acetonide)-OH[J]. Chinese Journal of Organic Chemistry, ;2020, 40(8): 2543-2546. doi: 10.6023/cjoc202004029 shu

Simple and Cost-Effective Synthesis of Fmoc-DOPA(acetonide)-OH

a.
Key Laboratory for Ultrafine Materials of Ministry of Education, Key Laboratory of Specially Functional Polymeric Materials and Related Technology, School of Materials Science and Engineering, East China University of Science and Technology, Shanghai 200237
b.
State Key Laboratory of Molecular Engineering of Polymers, Fudan University, Shanghai 200438

Corresponding author: Liu Runhui, rliu@ecust.edu.cn
Received Date: 19 April 2020
Revised Date: 13 May 2020
Available Online: 29 May 2020
Fund Project: the Fundamental Research Funds for the Central Universities 50321041917001Project supported by the National Natural Science Foundation of China (Nos. 21774031, 31800801), the Natural Science Foundation of Shanghai City (No. 18ZR1410300), and the Fundamental Research Funds for the Central Universities (Nos. 22221818014, 50321041917001)the Fundamental Research Funds for the Central Universities 22221818014the National Natural Science Foundation of China 21774031the Natural Science Foundation of Shanghai City 18ZR1410300the National Natural Science Foundation of China 31800801

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3, 4-Dihydroxyphenylalanine (DOPA) derivatives inspired by mussels have attracted broad interest in functional coatings of biomaterials and biomedical devices. Fmoc-DOPA(acetonide)-OH is the key precursor for solid-phase synthesis of adhesive mussel proteins and peptides. However, existing synthesis methods of Fmoc-DOPA(acetonide)-OH were tedious and costly which greatly hindered its practical application. Herein, a simple two-step strategy for preparing Fmoc-DOPA-(acetonide)-OH is reported, which is a simple and cost-effective synthesis method with broad application prospects.
- mussel adhesion protein,
- 3, 4-dihydroxyphenylalanine (DOPA),
- Fmoc-DOPA(acetonide)-OH,
- simple and efficient synthesis
1. [1]
  (a) Waite, J. H.; Qin, X. Biochemistry 2001, 40, 2887.
  (b) Kord Forooshani, P.; Lee, B. P. J. Polym. Sci., Part A: Polym. Chem. 2016, 55, 9.
  (c) Lee, B. P.; Messersmith, P. B.; Israelachvili, J. N.; Waite, J. H. Annu. Rev. Mater. Res. 2011, 41, 99.
2. [2]
  (a) Lee, H.; Dellatore, S. M.; Miller, W. M.; Messersmith, P. B. Science 2007, 318, 426.
  (b) Lee, H. A.; Ma, Y. F.; Zhou, F.; Hong, S.; Lee, H. Acc. Chem. Res. 2019, 52, 704.
  (c) Ye, Q.; Zhou, F.; Liu, W. M. Chem. Soc. Rev. 2011, 40, 4244.
3. [3]
  (a) Liu, Y.; Ai, K.; Lu, L. Chem. Rev. 2014, 114, 5057.
  (b) Wu, R.; Ding, X. K.; Qi, Y.; Zeng, Q.; Wu, Y. W.; Yu, B. R.; Xu, F. J. Small 2018, 14, 11.
  (c) Xu, M.; Khan, A.; Wang, T.; Song, Q.; Han, C.; Wang, Q.; Gao, L.; Huang, X.; Li, P.; Huang, W. ACS Appl. Bio Mater. 2019, 2, 3329.
  (d) Li, X. Y.; Gao, P.; Tan, J. Y.; Xiong, K. Q.; Maitz, M. F.; Pan, C. J.; Wu, H. K.; Chen, Y.; Yang, Z. L.; Huang, N. ACS Appl. Mater. Interfaces 2018, 10, 40844.
  (e) Pandey, N.; Hakamivala, A.; Xu, C. C.; Hariharan, P.; Radionov, B.; Huang, Z.; Liao, J.; Tang, L. P.; Zimmern, P.; Nguyen, K. T.; Hong, Y. Adv. Healthcare Mater. 2018, 7, 1701069.
4. [4]
  (a) Barclay, T. G.; Hegab, H. M.; Clarke, S. R.; Ginic-Markovic, M. Adv. Mater. Interfaces 2017, 4, 1601192.
  (b) Liu, X. S.; Cao, J. M.; Li, H.; Li, J. Y.; Jin, Q.; Ren, K. F.; Ji, J. ACS Nano 2013, 7, 9384.
  (c) Yang, C.; Ding, X.; Ono, R. J.; Lee, H.; Hsu, L. Y.; Tong, Y. W.; Hedrick, J.; Yang, Y. Y. Chem. Sci. 2014, 26, 7346.
  (d) Sheng, W. B.; Li, B.; Wang, X. L.; Dai, B.; Yu, B.; Jia, X.; Zhou, F. Chem. Sci. 2015, 6, 2068.
  (e) Zhang, S. X.; Liu, W. Y.; Dong, Y. S.; Wei, T.; Wu, Z. Q.; Chen, H. Langmuir 2019, 35, 3470.
  (f) Liu, L.; Tian, X. H.; Ma, Y.; Duan, Y. Q.; Zhao, X.; Pan, G. Q. Angew. Chem., Int. Ed. 2018, 57, 7878.
  (g) Wu, J. X.; Zheng, Y. J.; Jiang, S. B.; Qu, Y. C.; Wei, T.; Zhan, W. J.; Wang, L.; Yu, Q.; Chen, H. ACS Appl. Mater. Interfaces 2019, 11, 12357.
5. [5]
  (a) Zhao, Y. H.; Wu, Y.; Wang, L.; Zhang, M. M.; Chen, X.; Liu, M. J.; Fan, J.; Liu, J. Q.; Zhou, F.; Wang, Z. K. Nat. Commun. 2017, 8, 8.
  (b) Sheng, W. B.; Li, W.; Yu, B.; Li, B.; Jordan, R.; Jia, X.; Zhou, F. Angew. Chem., Int. Ed. 2019, 58, 12018.
  (c) Cong, Z. Q.; Zhang, L.; Ma, S. Q.; Lam, K. S.; Yang, F. F.; Liao, Y. H. ACS Nano 2020, 14, 1958.
6. [6]
  (a) Liu, L.; Tian, X. H.; Ma, Y.; Duan, Y. Q.; Zhao, X.; Pan, G. Q. Angew. Chem., Int. Ed. 2018, 57, 7878.
  (b) Kuang, J.; Messersmith, P. B. Langmuir 2012, 28, 7258.
  (c) Statz, A. R.; Meagher, R. J.; Barron, A. E.; Messersmith, P. B. J. Am. Chem. Soc. 2005, 127, 7972.
7. [7]
  Liu, Z.; Hu, B. H.; Messersmith, P. B. Tetrahedron Lett. 2008, 49, 5519. doi: 10.1016/j.tetlet.2008.07.052
8. [8]
  Messersmith, P. B.; Hu, B.-H.; Liu, Z. US 0087622, 2010.
9. [9]
  St-Georges, C.; Desilets, A.; Beliveau, F.; Ghinet, M.; Dion, S. P.; Colombo, E.; Boudreault, P. L.; Najmanovich, R. J.; Leduc, R.; Marsault, E. Eur. J. Med. Chem. 2017, 129, 110. doi: 10.1016/j.ejmech.2017.02.006
10. [10]
  Sever, M. J.; Wilker, J. J. Tetrahedron 2001, 57, 6139. doi: 10.1016/S0040-4020(01)00601-9
11. [11]
  (a) Tredwell, M.; Preshlock, S. M.; Taylor, N. J.; Gruber, S.; Huiban, M.; Passchier, J.; Mercier, J.; Génicot, C.; Gouverneur, V. Angew. Chem., Int. Ed. 2014, 53, 7751.
  (b) Liu, Z.; Hu, B. H.; Messersmith, P. B. Tetrahedron Lett. 2008, 49, 5519.
12. [12]
  oloshonok, V. A.; Ueki, H. Synthesis 2008, 693.
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