Biocatalytic synthesis of δ-gluconolactone and ε-caprolactone copolymers

Anamaria Todea, Valentin Badea, Lajos Nagy, Sándor Kéki, Carmen G. Boeriu, Francisc Péter

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5 Citations (Scopus)

Abstract

The biodegradability and biocompatibility properties of ε-caprolactone homopolymers place it as a valuable raw material, particularly for controlled drug delivery and tissue engineering applications. However, the usefulness of such materials is limited by their low hydrophilicity and slow biodegradation rate. In order to improve polycaprolactone properties and functionalities, copolymerization of ε-caprolactone with δ-gluconolactone was investigated. Since enzymatic reactions involving sugars are usually hindered by the low solubility of these compounds in common organic solvents, finding the best reaction medium was a major objective of this research. The optimal copolymerization conditions were set up by using different organic media (solvent and solvents mixtures), as well as solvent free systems that are able to dissolve (completely or partially) sugars, and are nontoxic for enzymes. Native and immobilized lipases by different immobilization techniques from Candida antarctica B and Thermomyces lanuginosus have been used as biocatalyst at 80°C. Although the main copolymer amount was synthesized in DMSO:t-BuOH (20:80) medium, the highest polymerization degrees, up to 16 for the copolymer product, were achieved in solventless conditions. The products, cyclic and linear polyesters, have been characterized by FT-IR and MALDI-TOF MS analysis. The reaction product analysis revealed the formation of cyclic products that could be the major impediment of further increase of the chain length.

Original languageEnglish
Pages (from-to)205-210
Number of pages6
JournalActa Biochimica Polonica
Volume61
Issue number2
Publication statusPublished - 2014

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Keywords

  • Biopolymers
  • Lipases
  • δ-gluconolactone
  • ε-caprolactone

ASJC Scopus subject areas

  • Biochemistry, Genetics and Molecular Biology(all)

Cite this

Todea, A., Badea, V., Nagy, L., Kéki, S., Boeriu, C. G., & Péter, F. (2014). Biocatalytic synthesis of δ-gluconolactone and ε-caprolactone copolymers. Acta Biochimica Polonica, 61(2), 205-210.