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Identification, cloning, expression and functional interrogation of the biosynthetic pathway of the polychlorinated triphenyls ambigol A–C from Fischerella ambigua 108b
Organic Chemistry Frontiers ( IF 4.6 ) Pub Date : 2020-08-20 , DOI: 10.1039/d0qo00707b Elke R. Duell 1, 2, 3, 4, 5 , Tobias M. Milzarek 1, 2, 3, 4, 5 , Mustafa El Omari 5, 6, 7, 8 , Luis J. Linares-Otoya 5, 9, 10, 11, 12 , Till F. Schäberle 5, 9, 10, 11, 12 , Gabrielle M. König 5, 6, 7, 8 , Tobias A. M. Gulder 1, 2, 3, 4, 5
Organic Chemistry Frontiers ( IF 4.6 ) Pub Date : 2020-08-20 , DOI: 10.1039/d0qo00707b Elke R. Duell 1, 2, 3, 4, 5 , Tobias M. Milzarek 1, 2, 3, 4, 5 , Mustafa El Omari 5, 6, 7, 8 , Luis J. Linares-Otoya 5, 9, 10, 11, 12 , Till F. Schäberle 5, 9, 10, 11, 12 , Gabrielle M. König 5, 6, 7, 8 , Tobias A. M. Gulder 1, 2, 3, 4, 5
Affiliation
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The terrestrial cyanobacterium Fischerella ambigua 108b produces the three polychlorinated triphenyls ambigol A–C that exhibit interesting antimicrobial, antiviral and cytotoxic activities. They are structurally related to polybrominated diphenylethers synthesized by diverse marine bacteria that are known to be highly toxic and are bioaccumulating in natural food webs. All ambigols display unusual connectivities: Ambigols A and B exhibit chlorination and ambigol C biaryl-ether bonds in the relative meta position at the central phenol unit, which is flanked by two 2,4-dichlorophenol units in all three compounds. Here we report on the identification of the biosynthetic gene cluster (BGC) reponsible for ambigol production in F. ambigua. After bioinformatic discovery of a putative ambigol BGC (ab) containing 10 genes, we cloned and heterologously expressed this cluster in Synechococcus elongatus PCC 7942 using Direct Pathway Cloning (DiPaC). In vivo and in vitro characterization of the two cytochrome P450 enzymes present in the ab BGC revealed complementary selectivity for either biaryl-ether bond (Ab2) or biaryl formation (Ab3) and provided a biosynthetic route to the ambigols.
中文翻译：
Fischerella ambigua 108b的多氯三苯基安比高AC的生物合成途径的鉴定，克隆，表达和功能研究
陆地蓝藻Fischerella ambigua 108b产生了三个多氯三苯酚Abigol A-C，它们表现出有趣的抗微生物，抗病毒和细胞毒性活性。它们在结构上与由多种海洋细菌合成的多溴二苯醚有关，这些海洋细菌已知具有剧毒并在天然食物网中生物蓄积。所有歧化物都显示出异常的连通性：Ambigols A和B在相对位置的中央酚单元的相对间位具有氯化和Ambigol C联芳醚键，在所有三个化合物中均侧接两个2，4-二氯酚单元。在这里，我们报告的负责F. ambigua生产安比高的生物合成基因簇（BGC）的鉴定。在生物信息学上发现了包含10个基因的假定的Ambigol BGC（ab）之后，我们使用直接途径克隆（DiPaC）在长Synechococcus elongatus PCC 7942中进行了克隆和异源表达。ab BGC中存在的两种细胞色素P450酶的体内和体外表征显示，对联芳基醚键（Ab2）或联芳基形成（Ab3）具有互补选择性，并提供了生物合成路线。
更新日期：2020-10-13
中文翻译：
Fischerella ambigua 108b的多氯三苯基安比高AC的生物合成途径的鉴定，克隆，表达和功能研究
陆地蓝藻Fischerella ambigua 108b产生了三个多氯三苯酚Abigol A-C，它们表现出有趣的抗微生物，抗病毒和细胞毒性活性。它们在结构上与由多种海洋细菌合成的多溴二苯醚有关，这些海洋细菌已知具有剧毒并在天然食物网中生物蓄积。所有歧化物都显示出异常的连通性：Ambigols A和B在相对位置的中央酚单元的相对间位具有氯化和Ambigol C联芳醚键，在所有三个化合物中均侧接两个2，4-二氯酚单元。在这里，我们报告的负责F. ambigua生产安比高的生物合成基因簇（BGC）的鉴定。在生物信息学上发现了包含10个基因的假定的Ambigol BGC（ab）之后，我们使用直接途径克隆（DiPaC）在长Synechococcus elongatus PCC 7942中进行了克隆和异源表达。ab BGC中存在的两种细胞色素P450酶的体内和体外表征显示，对联芳基醚键（Ab2）或联芳基形成（Ab3）具有互补选择性，并提供了生物合成路线。
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