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Molecules 2018, 23(2), 290; https://doi.org/10.3390/molecules23020290

Enzymatic Synthesis of Amino Acids Endcapped Polycaprolactone: A Green Route Towards Functional Polyesters

1
BioTeam/ICPEES-ECPM, UMR CNRS 7515, Université de Strasbourg, 25 rue Becquerel, 67087 Strasbourg CEDEX 2, France
2
J. SOUFFLET S. A., Centre de Recherche et d’Innovation Soufflet—Division Biotechnologies, Quai du Général Sarail, 10402 Nogent sur Seine CEDEX 2, France
*
Authors to whom correspondence should be addressed.
Received: 20 October 2017 / Revised: 15 January 2018 / Accepted: 23 January 2018 / Published: 30 January 2018
(This article belongs to the Special Issue Natural Polymers and Biopolymers)
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Abstract

ε-caprolactone (CL) has been enzymatically polymerized using α-amino acids based on sulfur (methionine and cysteine) as (co-)initiators and immobilized lipase B of Candida antarctica (CALB) as biocatalyst. In-depth characterizations allowed determining the corresponding involved mechanisms and the polymers thermal properties. Two synthetic strategies were tested, a first one with direct polymerization of CL with the native amino acids and a second one involving the use of an amino acid with protected functional groups. The first route showed that mainly polycaprolactone (PCL) homopolymer could be obtained and highlighted the lack of reactivity of the unmodified amino acids due to poor solubility and affinity with the lipase active site. The second strategy based on protected cysteine showed higher monomer conversion, with the amino acids acting as (co-)initiators, but their insertion along the PCL chains remained limited to chain endcapping. These results thus showed the possibility to synthesize enzymatically polycaprolactone-based chains bearing amino acids units. Such cysteine endcapped PCL materials could then find application in the biomedical field. Indeed, subsequent functionalization of these polyesters with drugs or bioactive molecules can be obtained, by derivatization of the amino acids, after removal of the protecting group. View Full-Text
Keywords: enzymatic polymerization; caprolactone; amino acids; methionine; cysteine; ring opening polymerization; Candida antarctica lipase B; polyester functionalization enzymatic polymerization; caprolactone; amino acids; methionine; cysteine; ring opening polymerization; Candida antarctica lipase B; polyester functionalization
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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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Duchiron, S.W.; Pollet, E.; Givry, S.; Avérous, L. Enzymatic Synthesis of Amino Acids Endcapped Polycaprolactone: A Green Route Towards Functional Polyesters. Molecules 2018, 23, 290.

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