journal article·2024-04Open access

A Single Amino Acid Able to Promote High‐Temperature Ring‐Opening Polymerization by Dual Activation

Elena Gabirondo, Katarzyna Świderek, Edurne Marin, Ainhoa Maiz‐Iginitz, Aitor Larranaga, Vicent Moliner, Agustin Etxeberria, Haritz Sardon

Advanced Science· Volume 11· Issue 16

Abstract

Abstract Amino acids are indispensable compounds in the body, performing several biological processes that enable proper functioning. In this work, it is demonstrated that a single amino acid, taurine, is also able to promote the ring‐opening polymerization (ROP) of several cyclic monomers under industrially relevant conditions. It is shown that the unique zwitterionic structure of taurine, where the negatively charged sulfonic acid group and the protonated amine group are separated by two methylene groups, not only provides high thermal stability but also leads to a dual activation mechanism, which is corroborated by quantum mechanical calculations. This unique mechanism allows for the synthesis of polylactide of up to 50 kDa in bulk at 180 °C with good end‐group fidelity using a highly abundant catalyst. Furthermore, cytotoxicity tests confirm that PLLA synthesized with taurine is non‐toxic. Moreover, it is demonstrated that the presence of taurine does not have any detrimental effect on the thermal stability of polylactide, and therefore polymers can be used directly without any post‐polymerization purification. It is believed that the demonstration that a simple structure composed of a single amino acid can promote polymerization can bring a paradigm shift in the preparation of polymers.
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Research context

OpenAlex topics: biodegradable polymer synthesis and properties · Carbon dioxide utilization in catalysis · Advanced Polymer Synthesis and Characterization

SciVX discovery tags are terminology-based. OpenAlex topics are source-provided classifications.

Affiliations

POLYMAT Department of Advanced Polymers and Materials: Physics, Chemistry and Technology Faculty of Chemistry University of the Basque Country UPV/EHU Manuel de Lardizabal 3 Pasealekua Donostia 20018 Spain

BioComp Group Institute of Advanced Materials (INAM), Universitat Jaume I Castelló 12071 Spain

Department of Mining‐Metallurgy Engineering and Materials Science, POLYMAT Faculty of Engineering in Bilbao University of the Basque Country (UPV/EHU) Plaza Torres Quevedo 1 Bilbao 48013 Spain

Center for Cooperative Research in Biomaterials (CIC biomaGUNE) Basque Research and Technology Alliance (BRTA) Paseo de Miramon 182 San Sebastián Spain

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