Issue 19, 2001
From the journal:

Chemical Communications

Peptide conjugation: unexpected ring opening of azacrown ether nucleophiles in the oxazolone-based couplingElectronic supplementary information (ESI) available: spectral data for representative examples of new compounds. See http://www.rsc.org/suppdata/cc/b1/b106106m/

Anatoly M. Belostotskii,*a   Elisheva Genizia  and  Alfred Hassnera  

* Corresponding authors

a Chemistry Department, Bar-Ilan University, Ramat-Gan, Israel
E-mail: belostot@mail.biu.ac.il

Abstract

Unexpected cleavage of the macrocyclic ring of secondary azacrown ethers when interacting with the Aib8 (Aib = α-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 α-amino acids in peptide synthesis.

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

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Article information

DOI
https://doi.org/10.1039/B106106M
Article type
Communication
Submitted
10 Jul 2001
Accepted
07 Aug 2001
First published
10 Sep 2001

Chem. Commun., 2001, 1960-1961

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

A. M. Belostotskii, E. Genizi and A. Hassner, Chem. Commun., 2001, 1960 DOI: 10.1039/B106106M

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