ChemInform Abstract: Macrocyclic Peptoids: N‐Alkylated Cyclopeptides and Depsipeptides

Abstract

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Multiple Multicomponent Macrocyclizations (MiBs): A Strategic Development Toward Macrocycle Diversity

“…MCR-based macrocyclization strategies are very suitable to generate highly diverse macrocyclic scaffolds displaying sufficient molecular complexity to resemble natural product-like ones. [8][9][10]14 Recently, this issue has been addressed by the development of a diversity-oriented strategy for macrocycle synthesis termed multiple multicomponent macrocyclization including bifunctional building blocks (MiB). 49 the first sections of this review will concentrate on the Ugivariant of MiBs to demonstrate the underlying principles of macrocycle formation and diversity generation followed by other multiple MCR macrocyclizations in later sections.…”

Consecutive isocyanide-based multicomponent reactions: synthesis of cyclic pentadepsipeptoids

“…Peptoids are an interesting class of non-natural compounds that have recently received much attention due to their wide range of biological activities, which makes them attractive candidates for drug discovery [1–7]. This family of oligomers comprising poly- N -substituted glycines mimics the primary natural structure of peptides and exhibits greater proteolytic stability and increased cellular permeabilities in comparison to peptides [5–7].…”

Applications of Convertible Isonitriles in the Ligation and Macrocyclization of Multicomponent Reaction-Derived Peptides and Depsipeptides

“…As depicted in Scheme , the approach devised to exploit the potential of convertible isonitriles on peptide chemistry comprises their utilization in the Ugi-4CR by reaction with a peptidic carboxylic acid, a primary amine and an oxo-compound to produce a larger peptide incorporating an N -alkylated amino acid, in this case preferentially Gly by the use of paraformaldehyde. The internal N -alkylation of peptides, and especially N -methylation, has proven to be a successful way to improve pharmacological properties such as metabolic stability, membrane permeability and pharmacokinetics, as compared with their non- N -alkylated congeners . As mentioned before, the reactivity of the C -terminal secondary amides derived from other convertible isocyanides has enabled their conversion to terminal carboxylic acids and esters, but not their utilization either in the direct ligation to another peptide fragment or in macrolactamization processes.…”