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

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

Research output: Contribution to journalArticlepeer-review

7 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)2950-2953
Number of pages4
JournalTetrahedron Letters
Volume52
Issue number23
DOIs
Publication statusPublished - 2011 Jun 8

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Fingerprint Dive into the research topics of 'Regio-selective hydroxylation of gem-difluorinated octanes by alkane hydroxylase (AlkB)'. Together they form a unique fingerprint.

Cite this