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首页> 外文期刊>Bioresources and Bioprocessing >2-Hydroxy-4-(3'-oxo-3'H-benzofura n-2'-yliden)but-2-enoic acid biosynthesis from dibenzofuran using lateral dioxygenation in a Pseudomonas putida strain B6-2 (DSM 28064)
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2-Hydroxy-4-(3'-oxo-3'H-benzofura n-2'-yliden)but-2-enoic acid biosynthesis from dibenzofuran using lateral dioxygenation in a Pseudomonas putida strain B6-2 (DSM 28064)

机译：在恶臭假单胞菌菌株B6-2中使用侧向双氧合作用从二苯并呋喃中合成2-羟基-4-（3'-氧代-3'H-苯并呋喃n-2'-丁烯）丁-2-烯酸（DSM 28064）

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Background: Benzofuran and its derivatives contain central pharmacophores and are important structures in medicinal chemistry. Chemical synthesis of benzofuran rings often requires expensive catalysts and stringent operational conditions. Biosynthesis is recognized as a promising way to save energy and produce valuable compounds. Dioxin biodegradation pathways can form several benzofuran derivatives, and these pathways may be a better choice for further synthesis of important biological compounds. 2-Hydroxy-4-(3'-oxo-3'H-benzofuran-2'-yliden)but-2-enoic acid (HOBB), a benzofuran derivative, can be biosynthesized from dibenzofuran (DBF) through co-metabolic degradation in a lateral dioxygenation pathway. Results: Efficient biosynthesis of HOBB was observed using whole cells of Pseudomonas putida strain B6-2. After cultivation in LB medium containing biphenyl, the cells were suspended to an OD_(600) of 5 to conduct biosynthesis in the presence of 0.5-mM DBF at pH 7 for 8 h. The bacterial cells were used twice to degrade approximately 0.70-mM DBF, and in batch process, accumulated about 0.29-mM HOBB. HOBB could be easily purified from the reaction with ethyl acetate using the neutral-acid extraction method, and 13.58 ± 0.31 mg of HOBB was obtained from 22.49 ± 0.74-mg DBF with an overall production yield of 60.4% (w/w). The product HOBB, which is a yellow powder, could be detected and identified by LC-MS, GC-MS, and NMR. Conclusions: In this study, a new biological route was developed to produce HOBB from DBF using whole cells of P. putida B6-2 (DSM 28064). The biosynthesis of HOBB may contribute to studies of the DBF lateral pathway and provide a new green route for synthesizing benzofuran derivatives with pharmacological activities.
机译：背景：苯并呋喃及其衍生物含有中心药效基团，并且是药物化学中的重要结构。苯并呋喃环的化学合成通常需要昂贵的催化剂和严格的操作条件。生物合成被认为是节省能源和生产有价值的化合物的有前途的方法。二恶英的生物降解途径可以形成几种苯并呋喃衍生物，这些途径可能是进一步合成重要生物化合物的更好选择。苯并呋喃衍生物2-羟基4-（3'-氧代-3'H-苯并呋喃-2'-丁烯基）丁-2-烯酸（HOBB）可以通过代谢分解由二苯并呋喃（DBF）生物合成在横向双加氧途径中结果：使用恶臭假单胞菌菌株B6-2的全细胞观察到了HOBB的高效生物合成。在含有联苯的LB培养基中培养后，将细胞悬浮至OD_（600）为5，在0.5 mM DBF和pH 7的存在下进行8 h生物合成。细菌细胞被使用两次以降解大约0.70-mM DBF，并且在分批过程中，积累了大约0.29-mM HOBB。使用中性酸萃取法可以很容易地从与乙酸乙酯的反应中纯化HOBB，从22.49±0.74 mg DBF中获得13.58±0.31 mg HOBB，总产率为60.4％（w / w）。可以通过LC-MS，GC-MS和NMR检测和鉴定黄色粉末状产物HOBB。结论：在这项研究中，开发了一种新的生物学途径，可利用恶臭假单胞菌B6-2（DSM 28064）的全细胞从DBF产生HOBB。 HOBB的生物合成可能有助于DBF侧向途径的研究，并为合成具有药理活性的苯并呋喃衍生物提供新的绿色途径。

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