Citation: Bing Wang, Chi Ma, Zuo-Chun Xiong, Cheng-Dong Xiong, Quan-Hua Zhou, Dong-Liang Chen. Synthesis of novel copolymer:Poly(p-dioxanone-co-L-phenylalanine)[J]. Chinese Chemical Letters, ;2013, 24(05): 392-396. shu

Synthesis of novel copolymer:Poly(p-dioxanone-co-L-phenylalanine)

  • Corresponding author: Dong-Liang Chen, 
  • Received Date: 26 December 2012
    Available Online: 26 February 2013

  • In order to expand the application of poly(p-dioxanone) or PPDO in biomedical area, a series of novel copolymers were synthesized successfully by one-step, melted copolymerization of p-dioxanone (PDO) and L-phenylalanine N-carboxyanhydride (L-Phe-NCA) monomers. With the in-feedmolar ratio of L-Phe-NCA/PDO equal to 1/20, the conversions of the two kinds of monomers were calculated from 1H NMR. The average molecular weight and polydispersity of the copolymer increase with the increasing reaction time and catalyst concentration. However, the conversions of the two kinds of monomers did not change with the reaction conditions. A three-step mechanism is presented and proved by high resolution 1H NMR and IR spectrums.
  • 加载中
    1. [1]

      [1] K.K. Yang, X.L. Wang, Y.Z. Wang, et al., Poly (p-dioxanone) and its copolymers, J. Macromol. Sci. Polym. Rev. 42 (2002) 373-398.

    2. [2]

      [2] R.B. Cady, J.A. Siegel, G. Mathien, et al., Physeal response to absorbable polydioxanone bone pins in growing rabbits, J. Biomed. Mater. Res. 48 (1999) 211-215.

    3. [3]

      [3] H.P. Greisler, D. Petsikas, T.M. Lam, et al., Kinetics of cell proliferation as a function of vascular graft material, J. Biomed. Mater. Res. 27 (1999) 955-961.

    4. [4]

      [4] N. Saito, T. Okada, H. Horiuchi, et al., A biodegradable polymer as a cytokine delivery system for inducing bone formation, Nat. Biotechnol. 19 (2001) 332-335.

    5. [5]

      [5] H. Wang, J.H. Dong, K.Y. Qiu, et al., Synthesis of poly(1,4-dioxan-2-one-co-trimethylenecarbonate) for application in drug delivery systems, J. Polym. Sci. Polym. Chem. 36 (1998) 1301-1307.

    6. [6]

      [6] M. Vert, Aliphatic polyesters: great degradable polymers that cannot do everything, Biomacromolecules 6 (2004) 538-546.

    7. [7]

      [7] K.K. Yang, L. Zheng, Y.Z. Wang, ABA triblock copolymers from poly(p-dioxanone) and poly(ethylene glycol), J. Appl. Polym. Sci. 102 (2006) 1092-1097.

    8. [8]

      [8] K.C. Remant Bahadur, S. Aryal, S. Raj Bhattarai, et al., Amphiphilic triblock copolymer based on poly(p-dioxanone) and poly(ethylene glycol): synthesis, characterization, and aqueous dispersion, J. Appl. Polym. Sci. 103 (2007) 2695-2702.

    9. [9]

      [9] X.L. Wang, Y.R. Mou, S.C. Chen, et al., A water-soluble PPDO/PEG alternating multiblock copolymer: synthesis, characterization, and its gel-sol transition behavior, Eur. Polym. J. 45 (2009) 1190-1197.

    10. [10]

      [10] G. Wu, S.C. Chen, Q. Zhan, et al., Well-defined amphiphilic poly(p-dioxanone)-grafted poly(vinyl alcohol) copolymers: synthesis and micellization, J. Polym. Sci. Part A: Polym. Chem. 48 (2010) 4811-4822.

    11. [11]

      [11] R. Chen, J.Y. Hao, C.D. Xiong, et al., Rapid synthesis of biodegradable poly(epsiloncaprolactone-co-p-dioxanone) random copolymers under microwave irradiation, Chin. Chem. Lett. 21 (2010) 249-252.

    12. [12]

      [12] H.Z. Zhao, J.Y. Hao, C.D. Xiong, et al., Different crystallinity of poly(D,L-lactide-cop-dioxanone) copolymers acquired by control of chain microstructure, Chin. Chem. Lett. 20 (2009) 1506-1509.

    13. [13]

      [13] H. Sun, F.H. Meng, A.A. Dias, et al., a-Amino acid containing degradable polymers as functional biomaterials: rational design, synthetic pathway, and biomedical applications, Biomacromolecules 12 (2001) 1937-1955.

    14. [14]

      [14] Y.D. Li, S.C. Chen, J.B. Zeng, et al., Novel biodegradable poly(1,4-dioxan-2-one) grafted soy protein copolymer: synthesis and characterization, Ind. Eng. Chem. Res. 47 (2008) 8233-8238.

    15. [15]

      [15] Z.B. Li, G.S. Zhao, L-phenylalanine specifically inhibited the proliferation of myocardial fibroblast in spontaneously hypertensive rat, Chin. J. Hypertens. 7 (1999) 163-165.

    16. [16]

      [16] P.J. Gao, D.L. Zhu, Y.M. Zhao, L-phenylalanine and smooth muscle cell proliferation from and WKY rats, Acta Phys. Sin. 50 (1998) 401-408.

    17. [17]

      [17] W.H. Daly, P. Drew, The preparation of N-carboxyanhydrides of [alpha]-amino acids using bis(trichloromethyl) carbonate, Tetrahedron Lett. 29 (1988) 5859-5862.

    18. [18]

      [18] T.J. Deming, Polypeptide materials: new synthetic methods and applications, Adv. Mater. 9 (1997) 299-311.

  • 加载中
    1. [1]

      Jia FuShilong ZhangLirong LiangChunyu DuZhenqiang YeGuangming Chen . PEDOT-based thermoelectric composites: Preparation, mechanism and applications. Chinese Chemical Letters, 2024, 35(9): 109804-. doi: 10.1016/j.cclet.2024.109804

    2. [2]

      Linghui ZouMeng ChengKaili HuJianfang FengLiangxing Tu . Vesicular drug delivery systems for oral absorption enhancement. Chinese Chemical Letters, 2024, 35(7): 109129-. doi: 10.1016/j.cclet.2023.109129

    3. [3]

      Wendi DouGuangying WanTiefeng LiuLin HanWu ZhangChuang SunRensheng SongJianhui ZhengYujing LiuXinyong Tao . Conductive composite binder for recyclable LiFePO4 cathode. Chinese Chemical Letters, 2024, 35(11): 109389-. doi: 10.1016/j.cclet.2023.109389

    4. [4]

      Xiaoning LiQuanyu ShiMeng LiNingxin SongYumeng XiaoHuining XiaoTony D. JamesLei Feng . Functionalization of cellulose carbon dots with different elements (N, B and S) for mercury ion detection and anti-counterfeit applications. Chinese Chemical Letters, 2024, 35(7): 109021-. doi: 10.1016/j.cclet.2023.109021

    5. [5]

      Shaojie DengPeihua MaQinghong BaiXin Xiao . The transformation of nor-seco-cucurbit[10]uril to cucurbit[5]uril and cucurbit[8]uril controlled by its own concentration. Chinese Chemical Letters, 2025, 36(2): 109878-. doi: 10.1016/j.cclet.2024.109878

    6. [6]

      Weidan MengYanbo ZhouYi Zhou . Green innovation unleashed: Harnessing tungsten-based nanomaterials for catalyzing solar-driven carbon dioxide conversion. Chinese Chemical Letters, 2025, 36(2): 109961-. doi: 10.1016/j.cclet.2024.109961

    7. [7]

      Ming-Yi SunLu ZhangYa LiChong-Chen WangPeng WangXueying RenXiao-Hong Yi . Recovering Ag+ with nano-MOF-303 to form Ag/AgCl/MOF-303 photocatalyst: The role of stored Cl ions. Chinese Chemical Letters, 2025, 36(2): 110035-. doi: 10.1016/j.cclet.2024.110035

    8. [8]

      Tong Zhou Liyi Xie Chuyu Liu Xiyan Zheng Bao Li . Between Sobriety and Intoxication: The Fascinating Journey of Sauce-Flavored Latte. University Chemistry, 2024, 39(9): 55-58. doi: 10.12461/PKU.DXHX202312048

    9. [9]

      Yiwen LinYijie ChenChunhui DengNianrong Sun . Integration of resol/block-copolymer carbonization and machine learning: A convenient approach for precise monitoring of glycan-associated disorders. Chinese Chemical Letters, 2024, 35(12): 109813-. doi: 10.1016/j.cclet.2024.109813

    10. [10]

      Qian WangTing GaoXiwen LuHangchao WangMinggui XuLongtao RenZheng ChangWen Liu . Nanophase separated, grafted alternate copolymer styrene-maleic anhydride as an efficient room temperature solid state lithium ion conductor. Chinese Chemical Letters, 2024, 35(7): 108887-. doi: 10.1016/j.cclet.2023.108887

    11. [11]

      Bharathi Natarajan Palanisamy Kannan Longhua Guo . Metallic nanoparticles for visual sensing: Design, mechanism, and application. Chinese Journal of Structural Chemistry, 2024, 43(9): 100349-100349. doi: 10.1016/j.cjsc.2024.100349

    12. [12]

      Yuan DongMutian MaZhenyang JiaoSheng HanLikun XiongZhao DengYang Peng . Effect of electrolyte cation-mediated mechanism on electrocatalytic carbon dioxide reduction. Chinese Chemical Letters, 2024, 35(7): 109049-. doi: 10.1016/j.cclet.2023.109049

    13. [13]

      Hongxia LiXiyang WangDu QiaoJiahao LiWeiping ZhuHonglin Li . Mechanism of nanoparticle aggregation in gas-liquid microfluidic mixing. Chinese Chemical Letters, 2024, 35(4): 108747-. doi: 10.1016/j.cclet.2023.108747

    14. [14]

      Yixin ZhangTing WangJixiang ZhangPengyu LuNeng ShiLiqiang ZhangWeiran ZhuNongyue He . Formation mechanism for stable system of nanoparticle/protein corona and phospholipid membrane. Chinese Chemical Letters, 2024, 35(4): 108619-. doi: 10.1016/j.cclet.2023.108619

    15. [15]

      Ping Wang Tianbao Zhang Zhenxing Li . Reconstruction mechanism of Cu surface in CO2 reduction process. Chinese Journal of Structural Chemistry, 2024, 43(8): 100328-100328. doi: 10.1016/j.cjsc.2024.100328

    16. [16]

      Wenzhong ZhangZirui YanLingcheng ChenYi Xiao . Sn-fused perylene diimides: Synthesis, mechanism, and properties. Chinese Chemical Letters, 2024, 35(10): 109582-. doi: 10.1016/j.cclet.2024.109582

    17. [17]

      Hai-Ling Wang Zhong-Hong Zhu Hua-Hong Zou . Structure and assembly mechanism of high-nuclear lanthanide-oxo clusters. Chinese Journal of Structural Chemistry, 2024, 43(9): 100372-100372. doi: 10.1016/j.cjsc.2024.100372

    18. [18]

      Jia-hui Li Jinkai Qiu Cheng Lian . Lithium-ion rapid transport mechanism and channel design in solid electrolytes. Chinese Journal of Structural Chemistry, 2025, 44(1): 100381-100381. doi: 10.1016/j.cjsc.2024.100381

    19. [19]

      Chunqing OuMeijia XiaoXinyue ZhengXianzhou HuangSuleixin YangYingying LengXiaowei LiuXiuqi LiangLinjiang SongYanjie YouShaohua YaoChangyang Gong . Programmable double-unlock nanocomplex self-supplies phenylalanine ammonia-lyase for precise phenylalanine deprivation of tumors. Chinese Chemical Letters, 2024, 35(8): 109275-. doi: 10.1016/j.cclet.2023.109275

    20. [20]

      Yubang Li Xixi Hu Daiqian Xie . The microscopic formation mechanism of O + H2 products from photodissociation of H2O. Chinese Journal of Structural Chemistry, 2024, 43(5): 100274-100274. doi: 10.1016/j.cjsc.2024.100274

Metrics
  • PDF Downloads(0)
  • Abstract views(586)
  • HTML views(4)

通讯作者: 陈斌, bchen63@163.com
  • 1. 

    沈阳化工大学材料科学与工程学院 沈阳 110142

  1. 本站搜索
  2. 百度学术搜索
  3. 万方数据库搜索
  4. CNKI搜索
Address:Zhongguancun North First Street 2,100190 Beijing, PR China Tel: +86-010-82449177-888
Powered By info@rhhz.net

/

DownLoad:  Full-Size Img  PowerPoint
Return