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Catalysts 2019, 9(3), 228; https://doi.org/10.3390/catal9030228

Synthesis of Mono- and Dithiols of Tetraethylene Glycol and Poly(ethylene glycol)s via Enzyme Catalysis

1
Department of Chemical and Biomolecular Engineering, The University of Akron, Akron, OH 44325, USA
2
Department of Food, Agricultural and Biological Engineering, The Ohio State University, Wooster, OH 44691, USA
*
Author to whom correspondence should be addressed.
Received: 11 February 2019 / Revised: 26 February 2019 / Accepted: 26 February 2019 / Published: 2 March 2019
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Abstract

This paper investigates the transesterification of methyl 3-mercaptopropionate (MP-SH) with tetraethylene glycol (TEG) and poly(ethylene glycol)s (PEG)s catalyzed by Candida antarctica Lipase B (CALB) without the use of solvent (in bulk). The progress of the reactions was monitored by 1H-NMR spectroscopy. We found that the reactions proceeded in a step-wise manner, first producing monothiols. TEG-monothiol was obtained in 15 min, while conversion to dithiol took 8 h. Monothiols from PEGs with Mn = 1000 and 2050 g/mol were obtained in 8 and 16 h, respectively. MALDI-ToF mass spectrometry verified the absence of dithiols. The synthesis of dithiols required additional fresh CALB and MP-SH. The structure of the products was confirmed by 1H-NMR and 13C-NMR spectroscopy. Enzyme catalysis was found to be a powerful tool to effectively synthesize thiol-functionalized TEGs and PEGs. View Full-Text
Keywords: Candida antarctica Lipase B; transesterification; polymer functionalization; tetraethylene glycol; poly(ethylene glycol) Candida antarctica Lipase B; transesterification; polymer functionalization; tetraethylene glycol; poly(ethylene glycol)
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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Mulay, P.; Shrikhande, G.; Puskas, J.E. Synthesis of Mono- and Dithiols of Tetraethylene Glycol and Poly(ethylene glycol)s via Enzyme Catalysis. Catalysts 2019, 9, 228.

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