Studies on the application of the Passerini reaction and enzymatic procedures to the synthesis of tripeptide mimetics |
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Authors: | Wiktor Szymanski Ryszard Ostaszewski |
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Affiliation: | a Faculty of Chemistry, Warsaw University of Technology, Noakowskiego 3, 00-664 Warszawa, Poland b Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland |
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Abstract: | A new, efficient method for the multicomponent synthesis of tripeptide mimetics is presented. Simple, chemoenzymatic transformations of Passerini reaction products enable the introduction of varied amino acid moieties into the tripeptide scaffold, with control of the stereochemistry. Additionally, this method allows the convenient introduction of a methyl group to the amide nitrogen, leading to derivatives of N-methylated amino acids—compounds of interest for medicinal chemistry. |
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Keywords: | Tripeptides Passerini reaction Enzymatic hydrolysis Non-coded amino acids N-Methylated peptides |
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