Journal article

Publication year: 2020

Pages: 3193-3201

Journal: Organic Chemistry Frontiers

Volume number: 7

Issue number: 20

ISSN: 2052-4129

Open access status: Hybrid

DOI Link: https://doi.org/10.1039/d0qo00707b

Publisher: Royal Society of Chemistry

Abstract: 
The terrestrial cyanobacteriumFischerella ambigua108b 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 relativemetaposition 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 inF. ambigua. After bioinformatic discovery of a putative ambigol BGC (ab) containing 10 genes, we cloned and heterologously expressed this cluster inSynechococcus elongatusPCC 7942 using Direct Pathway Cloning (DiPaC).In vivoandin vitrocharacterization of the two cytochrome P450 enzymes present in theabBGC revealed complementary selectivity for either biaryl-ether bond (Ab2) or biaryl formation (Ab3) and provided a biosynthetic route to the ambigols.

Harvard Citation style: Duell, E., Milzarek, T., El Omari, M., Linares-Otoya, L., Schäberle, T., König, G., et al. (2020) Identification, cloning, expression and functional interrogation of the biosynthetic pathway of the polychlorinated triphenyls ambigol A-C from Fischerella ambigua108b, Organic Chemistry Frontiers, 7(20), pp. 3193-3201. https://doi.org/10.1039/d0qo00707b

APA Citation style: Duell, E., Milzarek, T., El Omari, M., Linares-Otoya, L., Schäberle, T., König, G., & Gulder, T. (2020). Identification, cloning, expression and functional interrogation of the biosynthetic pathway of the polychlorinated triphenyls ambigol A-C from Fischerella ambigua108b. Organic Chemistry Frontiers. 7(20), 3193-3201. https://doi.org/10.1039/d0qo00707b