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2‐alkoxy‐5(4 H )‐oxazolones and the enantiomerization of N ‐alkoxycarbonylamino acids
Author(s) -
Benoiton N. Leo
Publication year - 1996
Publication title -
peptide science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.556
H-Index - 125
eISSN - 1097-0282
pISSN - 0006-3525
DOI - 10.1002/(sici)1097-0282(1996)40:2<245::aid-bip4>3.0.co;2-w
Subject(s) - oxazolone , chemistry , alkoxy group , aminolysis , amine gas treating , organic chemistry , base (topology) , medicinal chemistry , catalysis , mathematical analysis , alkyl , mathematics
N‐Alkoxycarbonylamino acids are chirally stable under normal conditions of coupling. In the presence of tert.amine (tertiary amine), most activated N‐alkoxycarbonylamino acids generate 2‐alkoxy‐5(4H)‐oxazolone, which is not chirally stable in the presence of the base. Consequently, enantiomerization occurs in the presence of tert.amine if the activated residue is not immediately consumed by aminolysis. This paper reviews the situations in which 2‐alkoxy‐5(4H)‐oxazolones are generated from N‐alkoxycarbonylamino acids, the enantiomerization that occurs during and after the incorporation of N‐alkoxycarbonylamino acids into peptides, the properties and methods of preparation of 2‐alkoxy‐5(4H)‐oxazolones, and the practical use that has been made from our knowledge of the chemistry of 2‐alkoxy‐5(4H)‐oxazolones. © 1996 John Wiley & Sons, Inc.