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Methionine and seleno-methionine type peptide and peptoid building blocks synthesized by five-component five-center reactions
- Kaluđerović, Goran N., Abbas, Muhammad, Kautz, Hans Christian, Wadaan, Mohammad A. M., Lennicke, Claudia, Seliger, Barbara, Wessjohann, Ludger A.
- Chemical communications 2017 v.53 no.26 pp. 3777-3780
- N-substituted glycines, ammonia, chemical reactions, gene expression, methionine, moieties, peptides, selenomethionine, selenoproteins
- 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).