Natural and Synthetic Halogenated Amino Acids—Structural and Bioactive Features in Antimicrobial Peptides and Peptidomimetics
- Resource Type
- Authors
- Mario Mardirossian; Marina Rubini; Mauro F. A. Adamo; Marco Scocchi; Michele Saviano; Alessandro Tossi; Renato Gennaro; Andrea Caporale
- Source
- Molecules, Vol 26, Iss 7401, p 7401 (2021)
Molecules
- Subject
- inorganic chemicals
α-and β-peptoid
Antimicrobial peptides (AMPs)
Halogenation
Proline
Fluoro-proline
Peptidomimetic
Pharmaceutical Science
Review
Microbial Sensitivity Tests
Bromo-tryptophan
Fluoro amino acids
Peptides
Structure-activity relationship
α-and β-peptoids
Anti-Bacterial Agents
Antimicrobial Peptides
Gram-Negative Bacteria
Gram-Positive Bacteria
Halogens
Humans
Peptidomimetics
Peptoids
Structure-Activity Relationship
Analytical Chemistry
QD241-441
halogenation
Anti-Bacterial Agent
Peptoid
Drug Discovery
Fluoro amino acid
Physical and Theoretical Chemistry
Microbial Sensitivity Test
structure-activity relationship
Antimicrobial Peptide
Organic Chemistry
fluoro-proline
antimicrobial peptides (AMPs)
fluoro amino acids
Chemistry (miscellaneous)
Halogen
bromo-tryptophan
Peptide
Molecular Medicine
α- and β-peptoids
Human
- Language
- ISSN
- 1420-3049
The 3D structure and surface characteristics of proteins and peptides are crucial for interactions with receptors or ligands and can be modified to some extent to modulate their biological roles and pharmacological activities. The introduction of halogen atoms on the side-chains of amino acids is a powerful tool for effecting this type of tuning, influencing both the physico-chemical and structural properties of the modified polypeptides, helping to first dissect and then rationally modify features that affect their mode of action. This review provides examples of the influence of different types of halogenation in amino acids that replace native residues in proteins and peptides. Examples of synthetic strategies for obtaining halogenated amino acids are also provided, focusing on some representative compounds and their biological effects. The role of halogenation in native and designed antimicrobial peptides (AMPs) and their mimetics is then discussed. These are in the spotlight for the development of new antimicrobial drugs to counter the rise of antibiotic-resistant pathogens. AMPs represent an interesting model to study the role that natural halogenation has on their mode of action and also to understand how artificially halogenated residues can be used to rationally modify and optimize AMPs for pharmaceutical purposes.