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Diol dehydratase accepts 3,3,3-trifluoro-1,2-propanediol as a relatively poor substrate, albeit without significant mechanism-based inactivation of the enzyme during catalysis. Optical and electron paramagnetic resonance (EPR) spectra revealed the steady-state formation of cob(II)alamin and a substrate-derived intermediate organic radical (3,3,3-trifluoro-1,2-dihydroxyprop-1-yl). The coenzyme undergoes Co\u2013C bond homolysis initiating a sequence of reaction by the generally accepted pathway via intermediate radicals. However, the greater steric size of trifluoromethyl and especially its negative impact on the stability of an adjacent radical centre compared to a methyl group has implications for the mechanism of the diol dehydratase reaction. Nevertheless, 3,3,3-trifluoropropionaldehyde is formed by the normal diol dehydratase pathway, but then undergoes non-enzymatic conversion into acetaldehyde, probably via 3,3-difluoropropenal and malonic semialdehyde.<\/jats:p>","DOI":"10.1093\/jb\/mvae047","type":"journal-article","created":{"date-parts":[[2024,7,11]],"date-time":"2024-07-11T05:10:48Z","timestamp":1720674648000},"page":"245-254","source":"Crossref","is-referenced-by-count":4,"title":["The action of coenzyme B12-dependent diol dehydratase on 3,3,3-trifluoro-1,2-propanediol results in elimination of all the fluorides with formation of acetaldehyde"],"prefix":"10.1093","volume":"176","author":[{"given":"Koichi","family":"Mori","sequence":"first","affiliation":[{"name":"Graduate School of Natural Science and Technology, Okayama University , Tsushima-naka, Kita-ku, Okayama 700-8530 , Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Bernard T","family":"Golding","sequence":"additional","affiliation":[{"name":"School of Natural and Environmental Sciences , Bedson Building, , Newcastle upon Tyne NE1 7RU , UK"},{"name":"Newcastle University , Bedson Building, , Newcastle upon Tyne NE1 7RU , UK"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Tetsuo","family":"Toraya","sequence":"additional","affiliation":[{"name":"Graduate School of Natural Science and Technology, Okayama University , Tsushima-naka, Kita-ku, Okayama 700-8530 , Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"286","published-online":{"date-parts":[[2024,7,11]]},"reference":[{"key":"2024090215362116000_ref1","volume-title":"Chemistry and Biochemistry of B12","author":"Banerjee","year":"1999"},{"key":"2024090215362116000_ref2","doi-asserted-by":"crossref","first-page":"27","DOI":"10.1146\/annurev.micro.60.080805.142216","article-title":"Radical enzymes in anaerobes","volume":"60","author":"Buckel","year":"2006","journal-title":"Ann. 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