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Enzyme catalysis of a novel phosphono migration

The last step in the biosynthesis of fosfomycin, an antibiotic used to treat diabetic foot infections and lower urinary tract infections, is catalysed by the non-haem-iron-dependent enzyme (S)-2-hydroxypropylphosphonate ((S)-2-HPP) epoxidase (HppE). The reaction involves an unusual dehydrogenation reaction in which the secondary alcohol of (S)-2-HPP is converted to the epoxide ring of fosfomycin. In this manuscript, the authors show that the enzyme can also catalyse a 1,2-phosphono-migration reaction, which is a biologically unprecedented chemical transformation. This finding could pave the way for the production of novel phosphonate-containing natural products and new phosphonate derivatives.

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