Home > Publications database > Catalytic cleavage of HEAT and subsequent covalent binding of the tetralone moiety by the SARS-CoV-2 main protease > print

001     437962
005     20250729150405.0
024 7 _ |a 10.1101/2020.05.02.043554
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024 7 _ |a 10.3204/PUBDB-2020-01727
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100 1 _ |a Guenther, Sebastian
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245 _ _ |a Catalytic cleavage of HEAT and subsequent covalent binding of the tetralone moiety by the SARS-CoV-2 main protease
260 _ _ |c 2020
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336 7 _ |a Preprint
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500 _ _ |a PrePrint: https://www.biorxiv.org/content/10.1101/2020.05.02.043554
520 _ _ |a Here 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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773 _ _ |a 10.1101/2020.05.02.043554
787 0 _ |a Oberthür, Dominik et.al.
|d Zenodo, 2020
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|t Raw diffraction data (CBF) for a structure of SARS-CoV-2 Main Protease bound to 2-Methyl-1-tetralone
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