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

Laurence M. Harwood, Simon J. Mountford, Ran Yan

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6 Citations (Scopus)

Abstract

3-Substituted-5-phenylmorpholinones have been demonstrated to act as N-protected C-terminus activated α-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.

Original languageEnglish
Pages (from-to)1-4
Number of pages4
JournalJournal of Peptide Science
Volume15
Issue number1
DOIs
Publication statusPublished - 2009
Externally publishedYes

Keywords

  • C-terminus
  • Morpholinone
  • Oxazalone
  • Synthesis

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