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Polymers 2017, 9(9), 403; https://doi.org/10.3390/polym9090403

Polyol Structure and Ionic Moieties Influence the Hydrolytic Stability and Enzymatic Hydrolysis of Bio-Based 2,5-Furandicarboxylic Acid (FDCA) Copolyesters

1
ACIB: Austrian Centre of Industrial Biotechnology GmbH, Konrad Lorenz Strasse 20, 3430 Tulln an der Donau, Austria
2
BASF SE, Carl-Bosch-Straße 38, 67056 Ludwigshafen am Rhein, Germany
3
BOKU, University of Natural Resources and Life Sciences, Institute for Environmental Biotechnology, Konrad Lorenz Strasse 20, 3430 Tulln an der Donau, Austria
Present address: AstraZeneca AB, Forskargatan 18, 151 85 Södertälje, Sweden
Present address: Richard Bittner AG, Ossiacherstrasse 7, A-9560 Feldkirchen, Austria
*
Author to whom correspondence should be addressed.
Received: 24 July 2017 / Revised: 13 August 2017 / Accepted: 23 August 2017 / Published: 30 August 2017
(This article belongs to the Special Issue Biodegradable and Biobased Polyesters)
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Abstract

A series of copolyesters based on furanic acid and sulfonated isophthalic acid with various polyols were synthetized and their susceptibility to enzymatic hydrolysis by cutinase 1 from Thermobifida cellulosilytica (Thc_Cut1) investigated. All copolyesters consisted of 30 mol % 5-sulfoisophthalate units (NaSIP) and 70 mol % 2,5-furandicarboxylic acid (FDCA), while the polyol component was varied, including 1,2-ethanediol, 1,4-butanediol, 1,8-octanediol, diethylene glycol, triethylene glycol, or tetraethylene glycol. The composition of the copolyesters was confirmed by 1H-NMR and the number average molecular weight (Mn) was determined by GPC to range from 2630 to 8030 g/mol. A DSC analysis revealed glass-transition temperatures (Tg) from 84 to 6 °C, which were decreasing with increasing diol chain length. The crystallinity was below 1% for all polyesters. The hydrolytic stability increased with the chain length of the alkyl diol unit, while it was generally higher for the ether diol units. Thc_Cut1 was able to hydrolyze all of the copolyesters containing alkyl diols ranging from two to eight carbon chain lengths, while the highest activities were detected for the shorter chain lengths with an amount of 13.6 ± 0.7 mM FDCA released after 72 h of incubation at 50 °C. Faster hydrolysis was observed when replacing an alkyl diol by ether diols, as indicated, e.g., by a fivefold higher release of FDCA for triethylene glycol when compared to 1,8-octanediol. A positive influence of introducing ionic phthalic acid was observed while the enzyme preferentially cleaved ester bonds associated to the non-charged building blocks. View Full-Text
Keywords: cutinase; Thermobifida cellulosilytica; bio-based; sulfonated isophthalic acid; poly(2,5-furan dicarboxylate) cutinase; Thermobifida cellulosilytica; bio-based; sulfonated isophthalic acid; poly(2,5-furan dicarboxylate)
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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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Haernvall, K.; Zitzenbacher, S.; Yamamoto, M.; Schick, M.B.; Ribitsch, D.; Guebitz, G.M. Polyol Structure and Ionic Moieties Influence the Hydrolytic Stability and Enzymatic Hydrolysis of Bio-Based 2,5-Furandicarboxylic Acid (FDCA) Copolyesters. Polymers 2017, 9, 403.

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