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Multicomponent reactions (MCRs) offer an attractive one-pot strategy for generating a library of highly functionalized and complex compounds like glycomimetics. [1] MCRs offer numerous advantages over traditional sequential reactions for the synthesis of diverse structurally demanding compounds. MCRs are applied in the synthesis of small drug-like molecule libraries, but also large and more complex molecules. Isocyanide-based MCRs, particularly Passerini and Ugi reactions, are of special importance, because they provide peptide-like compounds. The utility of the Passerini reaction relays on the mild reaction conditions required for the condensation of a carbonyl compound, a carboxylic acid and an isocyanide to afford peptide-like peptidomimetic products. [2] The three-component Passerini reaction is method to convert carbonyl compounds to α-acyloxyamides. [3] Passerini products were synthesized using three different isopropylidene-protected aldehydes (sorbose, galactose and allose derivative) as carbonyl components, amino acid-derived isocyanides (L and D) and acetic acid. Access to highly valuable building blocks, compounds with high degree of structural diversity can be obtained by post-condensation modification of Passerini products. Hydrolysis of Passerini products under basic conditions afforded α-hydroxy C-glycosyl acid derivatives. Further transformations afforted C-glycosyl amino acid dipeptide. Such derivatives are valuable monomers in the synthesis of glycomimetics (Figure 1). Carbohydrates and their derivatives are powerful tools in medicinal chemistry (interaction of proteins and oligosaccharides) and supramolecular chemistry (self-assembly, formation of different types of nanostructures). |
