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000437962 0247_ $$2doi$$a10.1101/2020.05.02.043554
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000437962 041__ $$aEnglish
000437962 1001_ $$0P:(DE-H253)PIP1082033$$aGuenther, Sebastian$$b0$$eCorresponding author
000437962 245__ $$aCatalytic cleavage of HEAT and subsequent covalent binding of the tetralone moiety by the SARS-CoV-2 main protease
000437962 260__ $$bZenodo$$c2020
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000437962 500__ $$aPrePrint: https://www.biorxiv.org/content/10.1101/2020.05.02.043554
000437962 520__ $$aHere we present the crystal structure of SARS-CoV-2 main protease (Mpro) covalently bound to 2-methyl-1-tetralone. This complex was obtained by co-crystallization of Mpro with HEAT (2-(((4-hydroxyphenethyl)amino)methyl)-3,4-dihydronaphthalen-1(2H)-one) in the framework of a large X-ray crystallographic screening project of Mpro against a drug repurposing library, consisting of 5632 approved drugs or compounds in clinical phase trials. Further investigations showed that HEAT is cleaved by Mpro in an E1cB-like reaction mechanism into 2-methylene-1-tetralone and tyramine. The catalytic Cys145 subsequently binds covalently in a Michael addition to the methylene carbon atom of 2-methylene-1-tetralone. According to this postulated model HEAT is acting in a pro-drug-like fashion. It is metabolized by Mpro, followed by covalent binding of one metabolite to the active site. The structure of the covalent adduct elucidated in this study opens up a new path for developing non-peptidic inhibitors.
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000437962 7001_ $$0P:(DE-H253)PIP1002913$$aBetzel, Christian$$b82
000437962 7001_ $$0P:(DE-H253)PIP1006208$$aMeents, Alke$$b83$$eCorresponding author
000437962 773__ $$a10.1101/2020.05.02.043554
000437962 7870_ $$0PUBDB-2020-01817$$aOberthür, Dominik et.al.$$dZenodo, 2020$$iIsParent$$r$$tRaw diffraction data (CBF) for a structure of SARS-CoV-2 Main Protease bound to 2-Methyl-1-tetralone
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