Peptide conjugation: unexpected ring opening of azacrown ether nucleophiles in the oxazolone-based coupling |
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| Authors: | Belostotskii A M Genizi E Hassner A |
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| Institution: | Chemistry Department, Bar-Ilan University, Ramat-Gan 52900, Israel. belostot@mail.biu.ac.il |
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| Abstract: | Unexpected cleavage of the macrocylic ring of secondary azacrown ethers when interacting with the Aib8 (Aib = alpha-aminoisobutyric acid) oxazolone indicates the possibility for a new mechanism of peptide racemization due to transformations of the oxazolones formed from the N-derivatives of alpha-amino acids in peptide synthesis. |
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