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Chemoenzymatic synthesis of sucrose‐containing aromatic polymers
Author(s) -
Park Hyun Gyu,
Chang Ho Nam,
Dordick Jonathan S.
Publication year - 2001
Publication title -
biotechnology and bioengineering
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.136
H-Index - 189
eISSN - 1097-0290
pISSN - 0006-3592
DOI - 10.1002/1097-0290(20010305)72:5<541::aid-bit1018>3.0.co;2-c
Subject(s) - chemistry , sucrose , polymer , organic chemistry
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′‐tereph‐ thalate 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°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 pro‐ vided 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 C1′, C6, and C6′ hydroxyls were maintained in the polymer backbones. © 2001 John Wiley & Sons, Inc. Biotechnol Bioeng 72: 541–547, 2001.