Enzymatic Fluorination in Streptomyces cattleya Takes Place with an Inversion of Configuration Consistent with an SN2 Reaction Mechanism
- 28 April 2004
- journal article
- Published by Wiley in ChemBioChem
- Vol. 5 (5) , 685-690
- https://doi.org/10.1002/cbic.200300839
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)‐[5‐2H1]‐ATP generated (5′R)‐[5‐2H1]‐5′‐FDA in a coupled enzyme assay involving SAM synthase and the fluorinase. The stereochemical analysis of the product relied on2H 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 SN2 reaction mechanism.Keywords
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