Thermoresponsive Oligo(ethylene glycol) Functionalized Poly-l-cysteine
作者： Xiaohui Fu , Yong Shen , Wenxin Fu , Zhibo Li
DOI: 10.1021/MA400678W
关键词: Methacrylate 、 Triphosgene 、 Ethylene glycol 、 Polymerization 、 Monomer 、 Polymer chemistry 、 Side chain 、 Michael reaction 、 Chemistry 、 Acrylate
摘要: A series of new functional amino acids were prepared in high yield via thiol–ene Michael addition between l-cysteine and monomethoxy oligo(ethylene glycol) (OEG) functionalized methacrylates (OEGxMA) acrylate (OEGxA). These OEGylated cysteine derivatives converted into polymerizable N-carboxyanhydride (NCA) monomers using triphosgene. Subsequent ring-opening polymerization (ROP) these NCA gave a poly-l-cysteine (poly-EGxMA-C or poly-EGxA-C) homopolypeptides. Depending on the length OEG side chains, poly-EGxMA-C poly-EGxA-C polypeptides displayed different solubility secondary structure water. More importantly, obtained can display reversible thermoresponsive properties water when x value is 3 5. The synthetic strategy represents highly efficient method to prepare nonionic with tunable properties.
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sci-hub.se 参考文章(47)
Jianjun Cheng, Timothy J. Deming, Synthesis of polypeptides by ring-opening polymerization of α-amino acid N-carboxyanhydrides. Topics in Current Chemistry. ,vol. 310, pp. 1- 26 ,(2011) , 10.1007/128_2011_173
Chongyi Chen, Zhaohui Wang, Zhibo Li, None, Thermoresponsive Polypeptides from Pegylated Poly-l-glutamates Biomacromolecules. ,vol. 12, pp. 2859- 2863 ,(2011) , 10.1021/BM200849M
Fang Liu, Marek W. Urban, Recent advances and challenges in designing stimuli-responsive polymers Progress in Polymer Science. ,vol. 35, pp. 3- 23 ,(2010) , 10.1016/J.PROGPOLYMSCI.2009.10.002
D SCHMALJOHANN, Thermo- and pH-responsive polymers in drug delivery. Advanced Drug Delivery Reviews. ,vol. 58, pp. 1655- 1670 ,(2006) , 10.1016/J.ADDR.2006.09.020
Bin Zhao, Dejin Li, Fengjun Hua, Derrick R. Green, Synthesis of Thermosensitive Water-Soluble Polystyrenics with Pendant Methoxyoligo(ethylene glycol) Groups by Nitroxide-Mediated Radical Polymerization Macromolecules. ,vol. 38, pp. 9509- 9517 ,(2005) , 10.1021/MA0514572
Kai-Steffen Krannig, Helmut Schlaad, pH-Responsive Bioactive Glycopolypeptides with Enhanced Helicity and Solubility in Aqueous Solution Journal of the American Chemical Society. ,vol. 134, pp. 18542- 18545 ,(2012) , 10.1021/JA308772D
Jessica R. Kramer, Timothy J. Deming, Preparation of multifunctional and multireactive polypeptides via methionine alkylation. Biomacromolecules. ,vol. 13, pp. 1719- 1723 ,(2012) , 10.1021/BM300807B
Zhibing Hu, Tong Cai, Chenglin Chi, Thermoresponsive oligo(ethylene glycol)-methacrylate- based polymers and microgels Soft Matter. ,vol. 6, pp. 2115- 2123 ,(2010) , 10.1039/B921150K
Brian D. Mather, Kalpana Viswanathan, Kevin M. Miller, Timothy E. Long, Michael addition reactions in macromolecular design for emerging technologies Progress in Polymer Science. ,vol. 31, pp. 487- 531 ,(2006) , 10.1016/J.PROGPOLYMSCI.2006.03.001
De-Cheng Wu, Ye Liu, Chao-Bin He, Thermal- and pH-Responsive Degradable Polymers Macromolecules. ,vol. 41, pp. 18- 20 ,(2008) , 10.1021/MA7024896