Chemoenzymatic synthesis of sucrose-containing aromatic polymers

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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 degreesC, >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(ethylene-terephthalamide), with sucrose contained in the polymer backbone. The polycondensation reactions were carried out in dimethylsulfoxide (DMSO) at 70 degreesC 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 C-13-NMR or H-1-NMR in DMSO provided a number average molecular weight of 3200 and 4300 Da, respectively. Structural analyses of the polymers were performed with H-1-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. (C) 2001 John Wiley & Sons, Inc.
Publisher
JOHN WILEY SONS INC
Issue Date
2001-03
Language
English
Article Type
Article
Keywords

ORGANIC-SOLVENTS; ENZYMATIC-SYNTHESIS; ESTERS

Citation

BIOTECHNOLOGY AND BIOENGINEERING, v.72, no.5, pp.541 - 547

ISSN
0006-3592
URI
http://hdl.handle.net/10203/20244
Appears in Collection
CBE-Journal Papers(저널논문)
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