Your browser version may not work well with NCBI's Web applications. More information here...
1: Org Lett. 2006 Dec 7;8(25):5849-52.Click here to read Links

(2R)- and (2S)-3-fluoroalanine and their N-methyl derivatives: synthesis and incorporation in peptide scaffolds.

Hoveyda HR, Pinault JF.

Tranzyme Pharma Inc., Institut de pharmacologie de Sherbrooke, 3001 12th Avenue Nord, Sherbrooke, Québec J1H 5N4, Canada. hhoveyda@tranzyme.com

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]

PMID: 17134288 [PubMed - indexed for MEDLINE]