Chemoenzymatic synthesis of sucrose-containing aromatic polymers

Hyun Gyu Park, Ho Nam Chang, Jonathan S. Dordick

Research output: Contribution to journalArticlepeer-review

5 Scopus citations

Abstract

A chemoenzymatic approach was developed to prepare sucrose-containing aromatic polymers. The protease from Bacillus licheniformis catalyzed the transesterification of sucrose with a diester of terephthalic acid in pyridine to give the mono- and diester products. At 45°C, >70% of sucrose was consumed after 1 day and sucrose diester began to form after 6 days when >95% of sucrose had been converted to sucrose monoester. The final yield of sucrose diester after 20 days was 13.8%. The sucrose monoester was identified as sucrose 1′-terephthalate and the diester products consisted of sucrose 6,1′-diterephthalate and sucrose 6′,1′-diterephthalate in a ratio of 2:1. The sucrose diester products were polymerized with ethylene-glycol and ethylene-diamine to give poly(ethylene-terephthalate) and poly(ethyleneterephthalamide), with sucrose contained in the polymer backbone. The polycondensation reactions were carried out in dimethylsulfoxide (DMSO) at 70°C using zinc acetate as a catalyst. The sucrose-containing polyester and polyamide were obtained at 65% yield for 24 h and at 73% yield for 12 h, respectively. End-group analysis of the polymers by 13C-NMR or 1H-NMR in DMSO provided a number average molecular weight of 3200 and 4300 Da, respectively. Structural analyses of the polymers were performed with 1H-NMR, 13C-NMR, and FTIR. On the basis of 13C-NMR, acylation of the C1′, C6, and C6′ hydroxyls were maintained in the polymer backbones.

Original languageEnglish
Pages (from-to)541-547
Number of pages7
JournalBiotechnology and Bioengineering
Volume72
Issue number5
DOIs
StatePublished - 5 Mar 2001
Externally publishedYes

Keywords

  • Aromatic polymers
  • Chemoenzymatic synthesis
  • Protease
  • Sucrose
  • Transesterification

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