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Merck

Synthesis of (2S,3S)-3'-fluoroisoleucine.

Organic & biomolecular chemistry (2004-02-27)
Jean-Damien Charrier, David S Hadfield, Peter B Hitchcock, Douglas W Young
ABSTRACT

The fluorinated amino acid, (2S,3S)-3'-fluoroisoleucine 3, has been synthesised by a route involving stereoselective cuprate or photochemical addition to the compound 4, derived in turn from (2S)-pyroglutamic acid. This provides a reporter group for the hydrophobic amino acid (2S)-isoleucine for use in protein studies.

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Sigma-Aldrich
2-Methyl-1-propenylmagnesium bromide solution, 0.5 M in THF