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Issue 31, 2018
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Formation of Nα-terminal 2-dialkyl amino oxazoles from guanidinated derivatives under mild conditions

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Abstract

Oxazole-containing peptides are an important class of molecules in medicinal chemistry programs. Here we describe a convenient solid-phase synthesis of Nα-terminal oxazole peptides. The strategy took advantage of an intramolecular rearrangement side reaction that occurred during the guanidination of the Nα-amino function of a peptide still anchored on the solid-support. The substitution map of the N,N-dialkylamino oxazole obtained using this strategy differed completely from the one achieved through the heterocyclization of the Ser or Thr side chain with the preceding carbonyl group, which is a common approach for the preparation of these compounds. This unexpected reaction was observed with N-terminal aromatic and aliphatic amino acids that have a Gly as the last before residue in both short as well as long peptides; however, it does not form the oxazole ring if Gly was substituted with other amino acids.

Graphical abstract: Formation of Nα-terminal 2-dialkyl amino oxazoles from guanidinated derivatives under mild conditions

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Publication details

The article was received on 21 Jun 2018, accepted on 16 Jul 2018 and first published on 17 Jul 2018


Article type: Paper
DOI: 10.1039/C8OB01463A
Citation: Org. Biomol. Chem., 2018,16, 5661-5666
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    Formation of Nα-terminal 2-dialkyl amino oxazoles from guanidinated derivatives under mild conditions

    S. A. H. Abdel Monaim, J. T. Mhlongo, A. Kumar, A. El-Faham, F. Albericio and B. G. de la Torre, Org. Biomol. Chem., 2018, 16, 5661
    DOI: 10.1039/C8OB01463A

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