Enzymatic fluorination in Streptomyces cattleya takes place with an inversion of configuration consistent with an SN2 reaction mechanism

Cosimo D. Cadicamo, Jacques Courtieu, Hai Deng, Abdelkrim Meddour, David O'Hagan (Corresponding Author)

Research output: Contribution to journalArticle

52 Citations (Scopus)

Abstract

The stereochemical course of the recently isolated fluorination enzyme from Streptomyces cattleya has been evaluated. The enzyme mediates a reaction between the fluoride ion and S- adenosyl-L-methionine (SAM) to generate 5'-fluoro-5'-deoxyadenosine (5'-FDA). Preparation of (5'R)-[5-(2)H(1)]-ATP generated (5'R)-[5-(2)H(1)]-5'-FDA in a coupled enzyme assay involving SAM synthase and the fluorinase. The stereochemical analysis of the product relied on (2)H NMR analysis in a chiral liquid-crystalline medium. It is concluded that the enzyme catalyses the fluorination with an inversion of configuration consistent with an S(N)2 reaction mechanism.

Original languageEnglish
Pages (from-to)685-690
Number of pages6
JournalChemBioChem
Volume5
Issue number5
Early online date28 Apr 2004
DOIs
Publication statusPublished - 3 May 2004

Fingerprint

Fluorination
Halogenation
Streptomyces
S-Adenosylmethionine
Enzymes
5-Methyltetrahydrofolate-Homocysteine S-Methyltransferase
Enzyme Assays
Fluorides
Adenosine Triphosphate
Ions
Assays
Nuclear magnetic resonance
Crystalline materials
Liquids
5'-fluoro-5'-deoxyadenosine

Keywords

  • bioorganic chemistry
  • fluorine
  • NMR spectroscopy
  • stereochemistry

Cite this

Enzymatic fluorination in Streptomyces cattleya takes place with an inversion of configuration consistent with an SN2 reaction mechanism. / Cadicamo, Cosimo D. ; Courtieu, Jacques ; Deng, Hai; Meddour, Abdelkrim ; O'Hagan, David (Corresponding Author).

In: ChemBioChem, Vol. 5, No. 5, 03.05.2004, p. 685-690.

Research output: Contribution to journalArticle

Cadicamo, Cosimo D. ; Courtieu, Jacques ; Deng, Hai ; Meddour, Abdelkrim ; O'Hagan, David. / Enzymatic fluorination in Streptomyces cattleya takes place with an inversion of configuration consistent with an SN2 reaction mechanism. In: ChemBioChem. 2004 ; Vol. 5, No. 5. pp. 685-690.
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