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Morpholinone mediated oxazolone‐free C ‐terminus amide coupling permitting a convergent strategy for peptide synthesis
Author(s) -
Harwood Laurence M.,
Mountford Simon J.,
Yan Ran
Publication year - 2009
Publication title -
journal of peptide science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.475
H-Index - 66
eISSN - 1099-1387
pISSN - 1075-2617
DOI - 10.1002/psc.1080
Subject(s) - oxazolone , amide , peptide , chemistry , peptide synthesis , stereochemistry , coupling (piping) , convergent synthesis , combinatorial chemistry , biochemistry , materials science , metallurgy
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. Copyright © 2008 European Peptide Society and John Wiley & Sons, Ltd.