Application of alicyclic β-amino acids in peptide chemistry

Abstract

The self-organizing beta-peptides have attracted considerable interest in the fields of foldamer chemistry and biochemistry. These compounds exhibit various stable secondary structure motifs that can be exploited to construct biologically active substances and nanostructured tertiary structures. The secondary structures can be controlled via the beta-amino acid sequence, and cyclic beta-amino acid residues play a crucial role in the design. The most important procedures for the preparation of cyclic beta-amino acid monomers and peptides are discussed in this tutorial review. Besides the secondary structure design principles, the methods of folded structure detection are surveyed.

Artificial Biocatalytic Linear Cascades to Access Hydroxy Acids, Lactones, and α- and β-Amino Acids

“…p-Hydroquinone formation was particularly high for the halogenated substrates, due to the lower pKa value and therefore better solubility and accessibility in the aqueous phase. Besides α-amino acids, their β-counterparts have attracted attention since they might be applied in the synthesis of bioactive compounds as well as in the design of hybrid peptides [61][62][63][64]. A biosynthetic route accessing various aromatic β-amino acids has been reported using a two-step-onepot cascade starting from β-keto esters.…”

Chiral differentiation of some cyclopentane and cyclohexane β-amino acid enantiomers through ion/molecule reactions

“…The chiral ␤-amino acids studied ( Figure 1) have attracted much interest due to their ability to work as stabilization agents in peptides, as modifying agents of peptides with biological activity, and as starting substances for different heterocycles [36,37], just to mention a few applications. Especially (1R,2S)-2-aminocyclopentanecarboxylic acid (cispentacin), which was isolated from Bacillus cereus and Streptomyces setonii, acts as an antifungal antibiotic [37].…”

“…Especially (1R,2S)-2-aminocyclopentanecarboxylic acid (cispentacin), which was isolated from Bacillus cereus and Streptomyces setonii, acts as an antifungal antibiotic [37].…”

Investigation of ring transformations of diaryl-β-lactams condensed with 1,3-benzothiazines

“…7 Many heterocycles have been prepared from compounds containing an azetidinone ring. 8 In the course of our recent studies on S-and N-containing condensed-skeleton heterocycles, we investigated reactions of 1,3-and 3,1-benzothiazines condensed with a β-lactam ring ( Figure 1).…”