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Green Polymer Chemistry: The Role of Candida Antarctica Lipase B in Polymer Functionalization

Castano Gil, Yenni Marcela
http://rave.ohiolink.edu/etdc/view?acc_num=akron1398034236

Abstract Details

2014, Doctor of Philosophy, University of Akron, Polymer Science.
The synthesis of functional polymers with well-defined structure, end-group fidelity and physico-chemical properties useful for biomedical applications has proven challenging. Chemo-enzymatic methods are an alternative strategy to increase the diversity of functional groups in polymeric materials. Specifically, enzyme-catalyzed polymer functionalization carried out under solventless conditions is a great advancement in the design of green processes for biomedical applications, where the toxicity of solvents and catalyst residues need to be considered. Enzymes offer several distinct advantages, including high efficiency, catalyst recyclability, and mild reaction conditions. This reseach aimed to precisely functionalized polymers using two methods: enzyme-catalyzed functionalization via polymerization and chemo-enzymatic functionalization of pre-made polymers for drug delivery. In the first method, well-defined poly(caprolactone)s were generated using alkyne-based initiating systems catalyzed by CALB. Propargyl alcohol and 4-dibenzocyclooctynol (DIBO) were shown to efficiently initiate the ring opening polymerization of e-caprolactone under metal free conditions and yielded polymers with Mn ~4 to 24 KDa and relatively narrow molecular mass distribution. In the second methodology, we present quantitative enzyme-catalyzed transesterification of vinyl esters and ethyl esters with poly(ethylene glycol)s (PEG)s that will serve as building blocks for dendrimer synthesis, followed by introducing a new process for the exclusive gamma-conjugation of folic acid. Specifically, fluorescein-acrylate was enzymatically conjugated with PEG. Additionally, halo-ester functionalized PEGs were successfully prepared by the transesterification of alkyl halo-esters with PEGs. 1H and 13C NMR spectroscopy, SEC and MALDI-ToF mass spectrometry confirmed the structure and purity of the products.
Judit E. Puskas, Dr. (Advisor)
Matthew L. Becker, Dr. (Advisor)
Chrys Wesdemiotis, Dr. (Committee Chair)
Toshikazu Miyoshi, Dr. (Committee Member)
Abraham Joy, Dr. (Committee Member)
Nic D. Leipzig, Dr. (Committee Member)
312 p.
Biomedical Research; Materials Science; Polymer Chemistry
enzymes; green polymer chemistry; halo-esters; functionalization of polymers; solventless conditions; ring opening polymerization; folate-conjugate polymer; PIB; PEG; PCL

Recommended Citations

Citations

  • Castano Gil, Y. M. (2014). Green Polymer Chemistry: The Role of Candida Antarctica Lipase B in Polymer Functionalization [Doctoral dissertation, University of Akron]. OhioLINK Electronic Theses and Dissertations Center. http://rave.ohiolink.edu/etdc/view?acc_num=akron1398034236

    APA Style (7th edition)

  • Castano Gil, Yenni Marcela. Green Polymer Chemistry: The Role of Candida Antarctica Lipase B in Polymer Functionalization. 2014. University of Akron, Doctoral dissertation. OhioLINK Electronic Theses and Dissertations Center, http://rave.ohiolink.edu/etdc/view?acc_num=akron1398034236.

    MLA Style (8th edition)

  • Castano Gil, Yenni Marcela. "Green Polymer Chemistry: The Role of Candida Antarctica Lipase B in Polymer Functionalization." Doctoral dissertation, University of Akron, 2014. http://rave.ohiolink.edu/etdc/view?acc_num=akron1398034236

    Chicago Manual of Style (17th edition)

akron1398034236
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© 2014, all rights reserved.
This open access ETD is published by University of Akron and OhioLINK.