Regio-selective hydroxylation of gem-difluorinated octanes by alkane hydroxylase (AlkB) |
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Authors: | Ravirala RamuChun-Wei Chang Ho-Husan ChouLi-Lan Wu Chih-Hsiang Chiang Steve S-F Yu |
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Institution: | a Institute of Chemistry, Academia Sinica, Taipei 115, Taiwan b Department of Chemistry, National Cheng Kung University, Tainan 701, Taiwan |
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Abstract: | gem-Difluoromethylene substituted molecules constitute a distinct class of fluorinated compounds. In this study, special chemistry has been developed for their preparation based on the highly selective terminal hydroxylation of these gem-difluorinated octanes by AlkB (alkane hydroxylase) from Pseudomonas putida Gpo1 to form gem-difluorinated octan-1-ols. The hydroxylation reaction is performed by whole-cell catalysis. Identification of the distal- and proximal-hydroxylation products was made by 1H, 13C, and 19F NMR; GC and GC/MSD; and/or by comparison with authentic standards in GC. To the best of our knowledge, we have obtained the first synthesis of 2,2-, 3,3- and 4,4-difluorooctan-1-ols, from simple and inexpensive starting materials. |
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Keywords: | Alkane hydroxylase C-H activation Enzyme catalysis Fluorinated substituents Octane Regio-selectivity |
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