title: (2R)- and (2S)-3-fluoroalanine and their N-methyl derivatives: synthesis and incorporation in peptide scaffolds.
abstract: A 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]
authors.affiliation: Tranzyme Pharma Inc., Institut de pharmacologie de Sherbrooke, 3001 12th Avenue Nord, Sherbrooke, Québec J1H 5N4, Canada. hhoveyda@tranzyme.com
authors.forename: Hamid R
authors.initials: HR
authors.lastname: Hoveyda
authors.forename: Jean-François
authors.initials: JF
authors.lastname: Pinault
mesh_terms: D000409:Alanine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D000577:Amides / Q000737:chemistry; D000596:Amino Acids; D007202:Indicators and Reagents; D013058:Mass Spectrometry; D008745:Methylation; D023303:Oxazolidinones / Q000138:chemical synthesis / Q000737:chemistry; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry; D012694:Serine / Q000737:chemistry
chemical_list: D000577:Amides; D000596:Amino Acids; D007202:Indicators and Reagents; D023303:Oxazolidinones; D010455:Peptides; C007742:3-fluoroalanine; D012694:Serine; D000409:Alanine