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However, the formation process of this intriguing dearomatization\/dimerization remains unknown. In this study, an unusual \u201cgene\u2010within\u2010gene\u201d thioesterase (TE) gene <jats:italic>ysfF<\/jats:italic> was functionally characterized. The gene was found to naturally encodes two proteins, an entire YsfF with \u03b1\/\u03b2\u2010hydrolase and 4\u2010hydroxybenzoyl\u2010CoA thioesterase (4\u2010HBT)\u2010like enzyme domains, and a nested YsfF<jats:sub>HBT<\/jats:sub> (4\u2010HBT\u2010like enzyme). Using an intracellular tagged carrier\u2010protein tracking (ITCT) strategy, in vitro reconstitution and in vivo experiments, we found that: i) both domains of YsfF displayed thioesterase activities; ii) YsfF\/YsfF<jats:sub>HBT<\/jats:sub> could accomplish the 6\u03c0\u2010electrocyclic ring closure for benzene ring formation; and iii) YsfF and cyclase YsfX together were responsible for the ACP\u2010tethered dearomatization\/dimerization process, possibly through an unprecedented Michael\u2010type addition reaction. Moreover, site\u2010directed mutagenesis experiments demonstrated that N301, E483 and H566 of YsfF are critical residues for both the 6\u03c0\u2010electrocyclization and dimerization processes. This study enhances our understanding of the multifunctionality of the TE protein family.<\/jats:p>","DOI":"10.1002\/anie.202402010","type":"journal-article","created":{"date-parts":[[2024,3,11]],"date-time":"2024-03-11T03:19:58Z","timestamp":1710127198000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":8,"title":["A Versatile Thioesterase Involved in Dimerization during Cinnamoyl Lipid Biosynthesis"],"prefix":"10.1002","volume":"63","author":[{"given":"Zirong","family":"Deng","sequence":"first","affiliation":[{"name":"State Key Laboratory for Crop Stress Resistance and High-Efficiency Production Shaanxi Key Laboratory of Natural Products &amp; Chemical Biology College of Chemistry &amp; Pharmacy Northwest A&amp;F University  Yangling, Shannxi 712100 China"},{"name":"Key Laboratory of Marine Drugs Ministry of Education School of Medicine and Pharmacy Ocean University of China  Qingdao Shandong 266003 China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Chunni","family":"Liu","sequence":"additional","affiliation":[{"name":"State Key Laboratory for Crop Stress Resistance and High-Efficiency Production Shaanxi Key Laboratory of Natural Products &amp; 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