2014/10/16 by Dawid Siodłak · 1 citation
Chemistry · Biochemistry, Genetics and Molecular Biology · Medicine · #Carbohydrate Chemistry and Synthesis #Chemical Synthesis and Analysis #Microbial Natural Products and Biosynthesis
paper · pdf · doi:10.1007/s00726-014-1846-4
openalex publication_date 2014/10/16 · openalex created_date 2025/10/10 · openalex updated_date 2026/07/31
α,β-Dehydroamino acids are naturally occurring non-coded amino acids, found primarily in peptides. The review focuses on the type of α,β-dehydroamino acids, the structure of dehydropeptides, the source of their origin and bioactivity. Dehydropeptides are isolated primarily from bacteria and less often from fungi, marine invertebrates or even higher plants. They reveal mainly antibiotic, antifungal, antitumour, and phytotoxic activity. More than 60 different structures were classified, which often cover broad families of peptides. 37 different structural units containing the α,β-dehydroamino acid residues were shown including various side chains, Z and E isomers, and main modifications: methylation of peptide bond as well as the introduction of ester group and heterocycle ring. The collected data show the relation between the structure and bioactivity. This allows the activity of compounds, which were not studied in this field, but which belong to a larger peptide family to be predicted. A few examples show that the type of the geometrical isomer of the α,β-dehydroamino acid residue can be important or even crucial for biological activity.