Selected β2-, β3- and β2,3-Amino Acid Heterocyclic Derivatives and Their Biological Perspective

Abstract

Heterocyclic moieties, especially five and six-membered rings containing nitrogen, oxygen or sulfur atoms, are broadly distributed in nature. Among them, synthetic and natural alike are pharmacologically active compounds and have always been at the forefront of attention due to their pharmacological properties. Heterocycles can be divided into different groups based on the presence of characteristic structural motifs. The presence of β-amino acid and heterocyclic core in one compound is very interesting; additionally, it very often plays a vital role in their biological activity. Usually, such compounds are not considered to be chemicals containing a β-amino acid motif; however, considering them as this class of compounds may open new routes of their preparation and application as new drug precursors or even drugs. The possibility of their application as nonproteinogenic amino acid residues in peptide or peptide derivatives synthesis to prepare a new class of compounds is also promising. This review highlights the actual state of knowledge about β-amino acid moiety-containing heterocycles presenting antiviral, anti-inflammatory, antibacterial compounds, anaplastic lymphoma kinase (ALK) inhibitors, as well as agonist and antagonists of the receptors.

Flat, Cα,β‐Didehydroalanine Foldamers with Ferrocene Pendants: Assessing the Role of α‐Peptide Dipolar Moments

“…However, efforts are continuously made also to mimic protein functions, but using β‐, γ‐ and δ‐amino acids, [3e,4] as well as other non‐coded α‐amino acids [5] . These residues are investigated for a variety of reasons: they impart enzymatic resistance to the peptides where they are inserted; [5j] they are contained in bioactive natural products; [5k] they increase peptide structural rigidity; [4] they are useful tools to build new 3D‐structures; [4b,5b] they can be exploited in bio‐organic and supramolecular chemistry [5c–e,j] …”

A transaminase with β-activity from Variovorax boronicumulans for the production of enantiopure β-amino acids

“…They are used in curing various neurological diseases like epilepsy or anxiety disorders [ [3] , [4] , [5] , [6] , [7] ] or to treat cancer [ 8 , 9 ]. They are important precursors for a huge variety of heterocyclic compounds [ 10 ] or can be applied in the production of therapeutical peptides [ 11 ]. These peptides fold into a similar shape as peptides consisting of their α-amino acid homologues [ [12] , [13] , [14] , [15] , [16] ], but they exhibit a higher resistance against proteolytic degradation [ [17] , [18] , [19] , [20] ].…”

5-Amino-3-methyl-Isoxazole-4-carboxylic Acid as a Novel Unnatural Amino Acid in the Solid Phase Synthesis of α/β-Mixed Peptides

“…Such unnatural amino acids are becoming an increasingly important tool in drug discovery and has led to an increase in the number of synthetic methods for the preparation of that class of compounds [ 9 , 10 , 11 ]. Peptidomimetics are still of a great interest in the development of new biologically active molecules [ 12 ]. The therapeutic application of peptides obtained from natural amino acids is limited due to the problems connected with the low stability against proteolysis.…”