Enzyme-Catalyzed Polymerization of Beta-alanine Esters, A Sustainable Route Towards the Formation of Poly-Beta-alanine

P. Steunenberg, M. Uiterweerd, M. Sijm, E.L. Scott, H. Zuilhof, J.P.M. Sanders, M.C.R. Franssen

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Abstract

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.
Original languageEnglish
Pages (from-to)682-690
JournalCurrent Organic Chemistry
Volume17
Issue number7
DOIs
Publication statusPublished - 2013

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Keywords

  • nitrogen-containing chemicals
  • ring-opening polymerization
  • amino-acids
  • organic-solvents
  • biobased production
  • peptides
  • lactams
  • lipases
  • biotransformations
  • esterification

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