Chemoenzymatic synthesis of sucrose-containing aromatic polymers

✍ Scribed by Hyun Gyu Park; Ho Nam Chang; Jonathan S. Dordick

• Publisher: John Wiley and Sons
• Year: 2001
• Tongue: English
• Weight: 146 KB
• Volume: 72
• Category: Article
• ISSN: 0006-3592
• DOI: 10.1002/1097-0290(20010305)72:5<541::aid-bit1018>3.0.co;2-c

✦ Synopsis

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 1Ј-terephthalate and the diester products consisted of sucrose 6,1Ј-diterephthalate and sucrose 6Ј,1Ј-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 13 C-NMR or 1 H-NMR in DMSO provided a number average molecular weight of 3200 and 4300 Da, respectively. Structural analyses of the polymers were performed with 1 H-NMR, 13 C-NMR, and FTIR. On the basis of 13 C-NMR, acylation of the C1Ј, C6, and C6Ј hydroxyls were maintained in the polymer backbones.