Regio-selective hydroxylation of gem-difluorinated octanes by alkane hydroxylase (AlkB)

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 Pseudo...

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Bibliographic Details
Published in:Tetrahedron letters 2011-06, Vol.52 (23), p.2950-2953
Main Authors: Ramu, Ravirala, Chang, Chun-Wei, Chou, Ho-Husan, Wu, Li-Lan, Chiang, Chih-Hsiang, Yu, Steve S.-F.
Format: Article
Language:English
Subjects:
Aliphatic compounds
Alkane hydroxylase
Bioconversions. Hemisynthesis
Biological and medical sciences
Biotechnology
Chemistry
C–H activation
Enzyme catalysis
Exact sciences and technology
Fluorinated substituents
Fundamental and applied biological sciences. Psychology
Methods. Procedures. Technologies
Octane
Organic chemistry
Preparations and properties
Regio-selectivity
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Summary: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.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2011.03.101