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

Ravirala Ramu, Chun Wei Chang, Ho-Hsuan Chou, Li Lan Wu, Chih Hsiang Chiang, Steve S.F. Yu

研究成果: Article

5 引文 (Scopus)

摘要

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.

原文English
頁(從 - 到)2950-2953
頁數4
期刊Tetrahedron Letters
52
發行號23
DOIs
出版狀態Published - 2011 六月 8

指紋

Octanes
Cytochrome P-450 CYP4A
Gems
Hydroxylation
Pseudomonas putida
Catalysis
Nuclear magnetic resonance
Molecules

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

引用此文

Ramu, Ravirala ; Chang, Chun Wei ; Chou, Ho-Hsuan ; Wu, Li Lan ; Chiang, Chih Hsiang ; Yu, Steve S.F. / Regio-selective hydroxylation of gem-difluorinated octanes by alkane hydroxylase (AlkB). 於: Tetrahedron Letters. 2011 ; 卷 52, 編號 23. 頁 2950-2953.
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Regio-selective hydroxylation of gem-difluorinated octanes by alkane hydroxylase (AlkB). / Ramu, Ravirala; Chang, Chun Wei; Chou, Ho-Hsuan; Wu, Li Lan; Chiang, Chih Hsiang; Yu, Steve S.F.

於: Tetrahedron Letters, 卷 52, 編號 23, 08.06.2011, p. 2950-2953.

研究成果: Article

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AU - Chiang, Chih Hsiang

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