Poly(γ-glutamic acid) esters with reactive functional groups suitable for orthogonal conjugation strategies

Journal of Polymer Science, Part A: Polymer Chemistry

Volumn 50, Issue 22, 2012, Pages 4790-4799

  Pacini, Aurora ^a   Caricato, Marco ^a   Ferrari, Stefania ^a   Capsoni, Doretta ^a   Martínez De Ilarduya, Antxon ^b   Muñoz Guerra, Sebastián ^b   Pasini, Dario ^a  

^a UNIVERSITY OF PAVIA   (Italy)

^b UNIVERSITAT POLITÈCNICA DE CATALUNYA   (Spain)

Author keywords

biopolymers; functionalization of polymers; poly( glutamic acid); polyamides; polyglutamate esters

Indexed keywords

AZIDE-ALKYNE CYCLOADDITION; BACTERIAL BIOPOLYMERS; BIOMEDICAL APPLICATIONS; BULK PROPERTIES; CLICK CHEMISTRY; ESTER GROUPS; FREE ACIDS; FUNCTIONALIZATION OF POLYMERS; GLUTAMIC ACID; MICROBIAL ORIGINS; POLYGLUTAMATE; POLYMER BACKBONES; PROPARGYL; RANDOM MICROSTRUCTURE; REACTION CONDITIONS; REACTIVE FUNCTIONAL GROUPS; SODIUM SALT; TAILORED PROPERTIES; THIOL-ENES; X-RAY DIFFRACTION TECHNIQUES;

ACETYLENE; AMIDES; AMINO ACIDS; BIOMOLECULES; BIOPOLYMERS; BROMINE COMPOUNDS; COPOLYMERS; CYCLOADDITION; DIFFERENTIAL SCANNING CALORIMETRY; ESTERIFICATION; FUNCTIONAL GROUPS; ITERATIVE METHODS; MEDICAL APPLICATIONS; POLYAMIDES; POLYMERS; STRUCTURE (COMPOSITION); THERMOGRAVIMETRIC ANALYSIS; X RAY DIFFRACTION;

ESTERS;

EID: 84867562419     PISSN: 0887624X     EISSN: 10990518     Source Type: Journal    
DOI: 10.1002/pola.26363     Document Type: Article

References (34)

1. Bajaj, I.,;, Singhal, R., Bioresour. Technol. 2011, 102, 5551-5561
2. (b), Akagi, T.,;, Baba, M.,;, Akashi, M., Polymer 2007, 48, 6729-6747
3. (c), Buescher, J. M.,;, Margaritis, A., Crit. Rev. Biotechnol. 2007, 27, 1-19
4. (d), Gross, R. A., In: Biopolymers from Renewable Resources;, Kaplan, D. L., Ed.; Springer: Berlin, 1998; Chapter 8, pp 195-218
5. (e), Shih, I. L.,;, Van, Y. T., Bioresour. Technol. 2001, 79, 207-225.
6. Selected examples: (a), Sakuma, S.,;, Sagawa, T.,;, Masaoka, Y.,;, Kataoka, M.,;, Yamashita, S.,;, Shirasaka, Y.,;, Tamai, I.,;, Ikumi, Y.,;, Kida, T.,;, Akashi, M., J. Control. Release 2009, 133, 125-31
7. (b), Portilla-Arias, J. A.,;, Camargo, B.,;, García-Alvarez, M.,;, Martínez de Ilarduya, A.,;, Muñoz-Guerra, S., J. Biomater. Sci. Polym. Ed. 2009, 20, 1065-1079
8. (c), Matsusaki, M.,;, Serizawa, T.,;, Kishida, A.,;, Akashi, M., Biomacromolecules 2005, 6, 400-407
9. (d), Chang, K.-Y.,;, Lin, C.-C.,;, Ho, G.-H.,;, Huang, Y.-P.,;, Lee, Y.-D., Polymer 2009, 50, 1755-1763.
10. Kubota, H.,;, Nambu, Y.,;, Endo, T., J. Polym. Sci. Part A: Polym. Chem. 1993, 31, 2877-2878
11. (b), Morillo, M.,;, Martínez de Ilarduya, A.,;, Muñoz-Guerra, S., Polymer 2003, 44, 7557-7564.
12. Prencipe, G.,;, Tabakman, S. M.,;, Welsher, K.,;, Liu, Z.,;, Goodwin, A. P.,;, Zhang, L.,;, Henry, J.,;, Dai, H., J. Am. Chem. Soc. 2009, 131, 4783-4787.
13. Barner-Kowollik, C.,;, Du Prez, F. E.,;, Espeel, P.,;, Hawker, C. J.,;, Junkers, T.,;, Schlaad, H.,;, Van Camp, W., Angew. Chem. Int. Ed. 2011, 50, 60-62.
14. Belkheira, M.,;, Pons, J.-M.,;, Bressy, C.,;, El Abed, D., Chem. Eur. J. 2011, 17, 12917-12921.
15. Irurzun, I.,;, Bou, J. J.,;, Pérez-Camero, G.,;, Abad, C.,;, Campos, A.,;, Muñoz-Guerra, S., Macromol. Chem. Phys. 2001, 202, 3253-3256.
16. Smith, M. B.,;, March, J., March's Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, 6th ed.; Wiley: New York, 2007.
17. Hoyle, C. E.,;, Bowman, C. N., Angew. Chem. Int. Ed. 2010, 49, 1540-1573.
18. Rostovtsev, V. V.,;, Green, L. G.,;, Fokin, V. V.,;, Sharpless, K. B., Angew. Chem. Int. Ed. 2002, 41, 2596-2599.
19. Using propargyl bromide (commercialized and used as an 80% solution in toluene) in the first step, lower conversion degrees were obtained. Furthermore, the products could not be completely purified.
20. Randall, J. C., Polymer Sequence Determination; Academic Press: New York, 1977; p 71.
21. 13C NMR spectroscopies, however, organic impurities were not detected in the final copolymers.
22. Benzyl, allyl, or propargyl esters have long been used as protecting groups for the carboxyl groups. Conditions for their selective removal are known: (a), Wuts, P., Greene's Protecting Groups in Organic Chemistry, 4th ed.; Wiley: New York, 2006, pp 590-602. See also
23. (b), Coluccini, C.,;, Dondi, D.,;, Caricato, M.,;, Taglietti, A.,;, Boiocchi, M.,;, Pasini, D., Org. Biomol. Chem. 2010, 8, 1640-1649.
24. Although outside the purpose of this article, an accurate comparison of the polymeric samples 1 with the corresponding copolymers after functionalization could be done with light scattering analytical techniques:, Wyatt, P., J. Anal. Chim. Acta 1993, 272, 1-40.
25. Portilla-Arias, J. A.,;, García-Alvarez, M.,;, Martínez de Ilarduya, A.,;, Muñoz-Guerra, S., Polym. Degrad. Stab. 2007, 92, 1916-1924.
26. Franz, N.,;, Menin, L.,;, Klok, H.-A., Eur. J. Org. Chem. 2009, 5390-5405
27. (b), Coluccini, C.,;, Metrangolo, P.,;, Parachini, M.,;, Pasini, D.,;, Resnati, G.,;, Righetti, P., J. Polym. Sci. Part A: Polym. Chem. 2008, 46, 5202-5213.
28. Pratt, R. C.,;, Lohmeijer, B. G.,;, Hedrick, J. L., Chem. Rev. 2007, 107, 5813-5840.
29. Hu, H.,;, Zhang, A.,;, Ding, L.,;, Lei, X.,;, Zhang, L., Molecules 2008, 13, 556-566
30. (b), Caricato, M.,;, Olmo, A.,;, Gargiulli, C.,;, Gattuso, G.,;, Pasini, D., Tetrahedron 2012, 68, 7861-7866.
31. (c), Cariati, E.,;, Lanzeni, V.,;, Tordin, E.,;, Ugo, R.,;, Botta, C.,;, Giacometti Schieroni, A.,;, Sironi, A.,;, Pasini, D., Phys. Chem. Chem. Phys. 2011, 13, 18005-18014
32. (d), Colombo, S.,;, Coluccini, C.,;, Caricato, M.,;, Gargiulli, C.,;, Gattuso, G.,;, Pasini, D., Tetrahedron 2010, 66, 4206-4211
33. (e), Boiocchi, M.,;, Bonizzoni, M.,;, Moletti, A.,;, Pasini, D.,;, Taglietti, A., New J. Chem. 2007, 31, 352-356.
34. Auras, R.,;, Harte, B.,;, Selke, S., Macromol. Biosci. 2004, 4, 835-864.