The synthesis of poly-ß-alanine by a lipase catalyzed polycondensation reaction between ß-alanine esters is reported. The effect of different solvents, reaction temperatures and substrate/enzyme concentrations on polymer yield and degree of polymerization (DP) was determined. Also the effect of methyl substituents at the a and ß position of ß-alanine was studied. Cross-Linked Enzyme Aggregates (CLEA) of Candida antarctica lipase B converted ß-alanine esters into polymers in high yield (up to 90%) and with high (DP) (up to 53 units). Optimum results were obtained when methyl esters are used in methyl tert-butyl ether (MTBE) as the solvent, at 50°C for 16 h.
- nitrogen-containing chemicals
- ring-opening polymerization
- biobased production
Steunenberg, P., Uiterweerd, M., Sijm, M., Scott, E. L., Zuilhof, H., Sanders, J. P. M., & Franssen, M. C. R. (2013). Enzyme-Catalyzed Polymerization of Beta-alanine Esters, A Sustainable Route Towards the Formation of Poly-Beta-alanine. Current Organic Chemistry, 17(7), 682-690. https://doi.org/10.2174/1385272811317070004