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Issue 26, 2017
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Methionine and seleno-methionine type peptide and peptoid building blocks synthesized by five-component five-center reactions

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Abstract

A first example of 5-component 5-center reactions with isonitriles [Ugi-5CRs] is described. The extended Ugi type reactions involve selenoaldehydes as well as ammonia, both challenging reactants in multicomponent (MCR) systems, to generate methionine and Se-methionine moieties and derivatives as protected building blocks or for direct ligation in peptides or peptoids. The peptoid/peptide building blocks proved to be non-cytotoxic but increased the expression of genes encoding for stress protective selenoproteins (Gpx1).

Graphical abstract: Methionine and seleno-methionine type peptide and peptoid building blocks synthesized by five-component five-center reactions

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Supplementary files

Article information


Submitted
16 Jan 2017
Accepted
02 Mar 2017
First published
02 Mar 2017

Chem. Commun., 2017,53, 3777-3780
Article type
Communication

Methionine and seleno-methionine type peptide and peptoid building blocks synthesized by five-component five-center reactions

G. N. Kaluđerović, M. Abbas, H. C. Kautz, M. A. M. Wadaan, C. Lennicke, B. Seliger and L. A. Wessjohann, Chem. Commun., 2017, 53, 3777
DOI: 10.1039/C7CC00399D

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