Peptide conjugation: unexpected ring opening of azacrown ether nucleophiles in the oxazolone-based coupling

Authors
Belostotskii, AM Genizi, E Hassner, A
Citation
Am. Belostotskii et al., Peptide conjugation: unexpected ring opening of azacrown ether nucleophiles in the oxazolone-based coupling, CHEM COMMUN, (19), 2001, pp. 1960-1961
Citations number
17
Categorie Soggetti
Chemistry
Journal title
CHEMICAL COMMUNICATIONS
ISSN journal
13597345 → ACNP
Issue
19
Year of publication
2001
Pages
1960 - 1961
Database
ISI
SICI code
1359-7345(20011007):19<1960:PCUROO>2.0.ZU;2-Y
Abstract
Unexpected cleavage of the macrocyclic ring of secondary azacrown ethers wh en interacting with the Aib(8) (Aib = alpha -aminoisobutyric acid) oxazolon e indicates the possibility for a new mechanism of peptide racemization due to transformations of the oxazolones formed from the N-derivatives of alph a -amino acids in peptide synthesis.