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

Anatoly M. Belostotskii; Elisheva Genizi; Alfred Hassner

doi:10.1039/b106106m

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

Anatoly M. Belostotskii
, Elisheva Genizi
, Alfred Hassner

Department of Chemistry

Bar-Ilan University

Research output: Contribution to journal › Article › peer-review

1 Scopus citations

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.

Original language	English
Pages (from-to)	1960-1961
Number of pages	2
Journal	Chemical Communications
Volume	1
Issue number	19
DOIs	https://doi.org/10.1039/b106106m
State	Published - 7 Oct 2001

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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.",

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AU - Hassner, Alfred

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AB - 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.

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

Abstract

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