An unusual bacterial polyester with a phenyl pendant group

An unusual bacterial polyester with a phenyl pendant group
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DOI:
10.1002/macp.1990.021910821
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发表时间:
1990-08
影响因子:
2.5
通讯作者:
K. Fritzsche;R. Lenz;R. Fuller
K. Fritzsche;R. Lenz;R. Fuller
中科院分区:
化学4区
文献类型:
--
作者:
K. Fritzsche;R. Lenz;R. Fuller

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已知微生物食油假单胞菌在营养限制条件下在正烷烃和正链烷酸上生长时产生含有3-羟基链烷酸酯单元的聚酯,但是当5-苯基戊酸作为唯一碳源提供时,产生聚[3-羟基-5-苯基戊酸酯],一种具有苯基侧基的聚酯。通过测定细胞生长和聚合物产量的变化,确定了最佳底物浓度和收获时间。12-L细胞培养物产生222.5mg聚合物/L和25%聚合物/细胞干重。这种细菌聚合物的旋光度为[α] = − 24.5 ° ± 0.2 °。通过1H NMR和13 C NMR光谱证实了结构。聚合物的组成也通过甲醇分解为重复单元的甲酯来测定,随后通过GC分析。通过该方法,发现聚酯在至少99%的程度上是均聚物。该聚酯具有在13°C下的玻璃化转变,54至69°C的熔融范围,和Mw = 350000的重均分子量,多分散性Mw/Mn为3.5,如通过GPC相对于聚苯乙烯标准物测定的。
The microorganism Pseudomonas oleovorans is known to produce polyesters containing 3-hydroxyalkanoate units when grown on n-alkanes and n-alkanoic acids under nutrient limiting conditions, but when 5-phenylvaleric acid was supplied as the only carbon source, poly[3-hydroxy-5-phenylpentanoate], a polyester with a phenyl pendant group, was produced. The optimum substrate concentrations and harvesting times were determined by measuring the change of cell growth and polymer yield during the growth. A 12-L cell culture yielded 222,5 mg polymer/L and 25% polymer per cellular dry weight. This bacterial polymer showed an optical rotation of [α] = −24,5° ± 0,2°. The structure was corroborated by 1H NMR and 13C NMR spectroscopy. The composition of the polymer was also determined by methanolysis to the methyl ester of the repeating unit, which was subsequently analyzed by GC. By this procedure the polyester was found to be a homopolymer to the extent of at least 99%. The polyester has a glass transition at 13°C, a melting range from 54 to 69°C, and a weight-average molecular weight of Mw = 350000 with a polydispersity Mw/Mn of 3,5, as determined by GPC relative to polystyrene standards.