Synthesis and Characterization of Poly(L-glutamic acid) with High Molecular Weight

Polymer - Plastics Technology and Engineering

Volumn 51, Issue 10, 2012, Pages 1062-1067

  Li, Hongchun ^a   Niu, Yongsheng ^a  

^a QINGDAO AGRICULTURAL UNIVERSITY   (China)

Author keywords

Biomaterials; Poly(L glutamic acid); Ring opening polymerization; Synthesis

Indexed keywords

BENZYL GROUP; CARBOXYL GROUPS; HIGH MOLECULAR WEIGHT; MOLAR RATIO; MONOMER CONCENTRATION; PALLADIUM HYDROXIDE; POLY (LGLUTAMIC ACID); REACTION TEMPERATURE;

AMINO ACIDS; BIOMATERIALS; POLYMERIZATION; SYNTHESIS (CHEMICAL);

MOLECULAR WEIGHT;

EID: 84864630296     PISSN: 03602559     EISSN: 15256111     Source Type: Journal    
DOI: 10.1080/03602559.2012.689055     Document Type: Article

References (34)

1. Gombotz, W.R.; Pettit, D.K. Biodegradable polymers for protein and peptide drug delivery. Bioconjug. Chem. 1995, 6, 332-351.
2. Zhu, G.Q.; Li, G.C.; Wang, P. Surface morphology and properties of poly(γ-benzyl l-glutamate)/poly(butyl acrylate-co-methyl methacrylate) blend film. Polym.-Plast. Technol. 2011, 50, 1470-1474.
3. El-Shafei, A.; Shaarawy, S.; Hebeish, A.Graft copolymerization of chitosan with butyl acrylate and application of the copolymers to cotton fabric. Polym.-Plast. Technol.2005, 44, 1523-1535.
4. Raju, G.; Ratnam, C.T.; Ibrahim, N.A.; Rahman, M.Z.A.; Yunus, W.M.Z.W. Graft copolymerization of methyl acrylate onto oil palm empty fruit bunch (OPEFB) fiber. Polym.-Plast. Technol. 2007, 46, 949-955.
5. Hua, H.; Dube, M.A. Semi-continuous emulsion copolymerization of styrene-butyl acrylate with methacrylic acid: Screening design of experiments. Polym.-Plast. Technol. 2011, 50, 349-361.
6. III(2,4-dinitrophenoxy) and lewis-basic cocatalyst. J. Polym. Sci. Pt A: Polym. Chem. 2007, 45, 5050-5056.
7. Niu, Y.S.; Zhang, W.X.; Li, H.C.; Chen, X.S.; Sun, J.R.; Zhuang, X.L.; Jing, X.B. Carbon dioxide/propylene oxide coupling reaction catalyzed by chromium salen complexes. Polymer 2009, 50, 441-446.
8. Niu, Y.S.; Li, H.C.; Chen, X.S.; Zhang, W.X.; Zhuang, X.L.; Jing, X.B. Alternating copolymerization of carbon dioxide and propylene oxide catalyzed by cobalt Schiff base complex. Macromol. Chem. Phys. 2009, 210, 1224-1229.
9. Hassan, M.A.; Kozlowski, R.; Obidzinski, B.; Shehata, A.B.; Aziz, F.A. The effect of new flame retardant systems containing montmorillonite-butyl acrylate nanoclay on the flammability properties of polyuerethane polymer. Polym.-Plast. Technol. 2007, 46, 521-527.
10. Xu, N.; Xiao, C.; Feng, Y.; Song, Z.; Zhang, Z.; An, S. Study on absorptive property and structure of resin copolymerized by butyl methacrylate with hydroxyethyl methacrylate. Polym.-Plast. Technol. 2009, 48, 716-722.
11. 4 catalyst system and epoxidation of the resulting copolymer. Polymer 2008, 49, 2839-2844.
12. 4 Catalyst Systems. J Appl. Polym. Sci. 2011, 121, 3085-3092.
13. Kricheldorf, H.R. α-Amino acid-N-carboxy-Anhydrides and Related Heterocycles, Springer-Verlag: Berlin, 1987.
14. Li, S.C.; Peng, W.J.; Lu, X.P. Effects of fillers and other LIPN on damping of PS = P(EA-nBA) LIPNs. Int. J. Polym. Mater. 1995, 29, 37-42.
15. Sivapitchai, S.; Vajjiravel, M.; Umapathy, M.J. Polymerization of butyl acrylate using potassium peroxy disulfate as initiator in the presence of phase transfer catalyst-A kinetic study. Int. J. Polym. Mater. 2006, 55, 537-548.
16. Albain, K.S.; Belani, C.P.; Bonomi, P.; Byrne, K.J.; Schiller, J.H.; Socinski, M. PIONEER: A phase III randomized trial of paclitaxel poliglumex versus paclitaxel in chemotherapy-naive women with advanced-stage non-small-cell lung cancer and performance status of 2. Clin. Lung Cancer 2006, 7, 417-419.
17. Morgan, M.A.; Darcy, K.M.; Rose, P.G.; Degeest, K.; Bookman, M.A.; Aikins, J.K.; Sill, M.W.; Mannel, R.S.; Allievi, C.; Egorin, M. Paclitaxel poliglumex and carboplatin as first-line therapy in ovarian, peritoneal or fallopian tube cancer: A phase I and feasibility trial of the Gynecologic Oncology Group. J. Gynecol Oncol. 2008, 110, 329-335.
18. Lin, J.P.; Zhu, G.Q.; Zhu, X.M.; Lin, S.L.; Nose, T.; Ding, W.W. Aggregate structure change induced by intramolecular helix-coil transition. Polymer 2008, 49, 1132-1136.
19. Hanby, W.E.; Waley, S.G.; Watson, J. Synthetic polypeptides Part II: Polyglutamic acid. J. Chem. Soc. 1950, 3239-3249.
20. Doty, P.; Wada, A.; Yang, J.T.; Blout, E.R. Polypeptides. VIII. Molecular configurations of poly-L-glutamic acid in water-dioxane solution. J. Poly. Sci. 1957, 104, 851-861.
21. O'Brien, M.E.; Socinski, M.A.; Popovich, A.Y.; Bondarenko, I.N.; Tomova, A.; Bilynsky, B.T.; Hotko, Y.S.; Ganul, V.L.; Kostinsky, I.Y.; Eisenfeld, A.J.; Sandalic, L.; Oldham, F.B.; Bandstra, B.; Sandler, A.B.; Singer, J.W. Randomized phase III trial comparing singleagent paclitaxel Poliglumex (CT-2103, PPX) with single-agent gemcitabine or vinorelbine for the treatment of PS 2 patients with chemotherapy-naive advanced non-small cell lung cancer. J. Thorac. Oncol. 2008, 3, 728-734.
22. Ihre, H.; Padilla de Jesus, O.L.; Frechet, J.M.J. Fast and convenient divergent synthesis of aliphatic ester dendrimers by anhydride coupling. J. Am. Chem. Soc. 2001, 123, 5908-5917.
23. Lin, J.P.; Zhu, J.Q.; Chen, T.; Lin, S.L.; Cai, C.H.; Zhang, L.S.; Zhuang, Y.; Wang, X.S. Drug releasing behavior of hybrid micelles containing polypeptide triblock copolymer. Biomaterials 2009, 30, 108-117.
24. Grayson, S.M.; Fréchet, J.M.J. Divergent synthesis of dendronized poly(p-hydroxystyrene. Macromolecules 2001, 34, 6542-6544.
25. Daly, W.H.; Poche, D. The Preparation of N-carboxyanhydrides of α-amino acids using bis (trichioromethyl) carbonate. Tetrahedr. Lett. 1988, 29, 5859-5862.
26. Zhu, G.Q.; Feng, L.; Zhang, S.N. Factors of influencing the grafting ratio of poly(c-benzyl L-glutamate)-graft-poly(ethylene glycol) copolymer. J. Macromol. Sci. A 2009, 46, 694-698.
27. Lee, M.Y.; Kim, S.H.; Ganapathy, H.S.; Kim, S.W.; Lim, K.T. Characterization of micellar film morphologies of semifluorinated block copolymers by AFM. Ultramicroscopy 2008, 108, 1210-1214.
28. Woodward, R.B.; Schramm, C.H. Syn- thesis of Protein Analogs. J. Am. Chem. Soc. 1947, 69, 1551-1552.
29. Cho, C.S.; Jeong, Y.I.; Kim, S.H.; Nah, J.W.; Kubota, M.; Komoto, T. Thermoplastic hydrogel based on hexablock copolymer composed of poly(c-benzyl L-glutamate) and poly(ethylene oxide). Polymer 2000, 41, 5185-5193.
30. Sela, M.; Berger, A. The synthesis and spectrophotometric study of poly-L-tyrosine and poly-3,5-diiodotyrosine. J. Am. Chem. Soc. 1953, 75, 6350-6351.
31. Sela, M.; Berger, A. The terminal groups of poly- or-amino acids. J. Am. Chem. Soc. 1955, 77, 1893-1898.
32. Idelson, M.; Blout, E.R. High molecular weight poly-L-glutamic acid: Preparation and optical rotation changes. J. Am. Chem. Soc. 1958, 80, 4631-4634.
33. Wang, D.; Feng, X.D. Synthesis of Poly(glycolic acid-alt-L-aspartic acid) from a Morpholine-2,5-dione Derivative. Macromolecules 1997, 30, 5688-5692.
34. He, B.; Bei, J.Z.; Wang, S.G. Synthesis and characterization of a functionalized biodegradable copolymer. Polymer 2003, 44, 989-994.