Enzyme-Catalyzed Polymerization of Beta-alanine Esters, A Sustainable Route Towards the Formation of Poly-Beta-alanine
Steunenberg, P. ; Uiterweerd, M. ; Sijm, M. ; Scott, E.L. ; Zuilhof, H. ; Sanders, J.P.M. ; Franssen, M.C.R. - \ 2013
Current Organic Chemistry 17 (2013)7. - ISSN 1385-2728 - p. 682 - 690.
nitrogen-containing chemicals - ring-opening polymerization - amino-acids - organic-solvents - biobased production - peptides - lactams - lipases - biotransformations - esterification
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.