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

Lookup NU author(s): Dr Ran Yan


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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.

Publication metadata

Author(s): Harwood LM, Mountford SJ, Yan R

Publication type: Article

Publication status: Published

Journal: Journal of Peptide Science

Year: 2009

Volume: 15

Issue: 1

Pages: 1-4

ISSN (print): 1075-2617

ISSN (electronic): 1099-1387

Publisher: John Wiley & Sons Ltd.


DOI: 10.1002/psc.1080


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