Morpholinone mediated oxazolone-free C-terminus amide coupling permitting a convergent strategy for peptide synthesis

Harwood, L.M. ORCID: https://orcid.org/0000-0002-8442-7380, Mountford, S.J. and Yan, R. (2009) Morpholinone mediated oxazolone-free C-terminus amide coupling permitting a convergent strategy for peptide synthesis. Journal of Peptide Science, 15 (1). pp. 1-4. ISSN 1075-2617 doi: 10.1002/psc.1080

Abstract/Summary

3-Substituted-5-phenylmorpholinones have been demonstrated to act as N-protected C-terminus activated alpha-amino acids capable of undergoing solution phase N-terminus peptide extension following standard coupling procedures. The N-acylated morpholinones do not undergo epimerisation of the stereocentre of the C-terminus amino acid residue as oxazolone formation is sterically prevented, although C-terminus peptide coupling is still possible. This convergent approach to peptide synthesis is exemplified by the preparation of L-ala-L-ala-L-ala and L-ala-D-ala-L-ala. Copyright (c) 2008 European Peptide Society and John Wiley & Sons, Ltd.