Hamid R Hoveyda, Jean-François Pinault
Tranzyme Pharma Inc., Institut de pharmacologie de Sherbrooke, 3001 12th Avenue Nord, Sherbrooke, Québec J1H 5N4, Canada. hhoveyda@tranzyme.com
Organic letters 2006 Dec 7A convergent synthetic methodology has been developed to access both (2S)- and (2R)-3-fluoroalanine and their corresponding N-methyl analogues, in optically pure form, through a common oxazolidinone intermediate that can be obtained from L- or D-serine. In addition, a procedure for incorporation of these unnatural amino acids in peptide scaffolds is also disclosed herein that minimizes the occurrence of beta-elimination during amide bond formation. [reaction: see text]
Hamid R Hoveyda, Jean-François Pinault. 2R)- and (2S)-3-fluoroalanine and their N-methyl derivatives: synthesis and incorporation in peptide scaffolds. Organic letters. 2006 Dec 7;8(25):5849-52
PMID: 17134288
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