Carborane-containing amino acids and peptides: Synthesis, properties and applications

• Published in: Coordination chemistry reviews Vol. 433; p. 213753
• Main Authors: Gruzdev, Dmitry A., Levit, Galina L., Krasnov, Victor P., Charushin, Valery N.
• Format: Journal Article
• Language: English
• Published: Elsevier B.V 15-04-2021
• Subjects: Amino acids; BNCT; Carboranes; Chirality; Peptides; Piezoelectric activity; Carboranes; Piezoelectric activity; Amino acids; BNCT; Peptides; Chirality
• ISSN: 0010-8545; 1873-3840
• DOI: 10.1016/j.ccr.2020.213753

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•Carboranyl amino acids and peptides are mainly designed for medicinal chemistry.•Carborane moieties in the structure of amino acids / peptides alter their properties.•Chirality of carboranyl amino acids is discussed.•Some carboranyl amino acids possess piezoelectric activity.
Derivatives of dicarba-closo-dodecaboranes and dicarba-nido-undecaboranes (carboranes) are of increasing interest for modern medicinal chemistry and materials science. The combination of carborane residues and amino acid fragments in one structure can serve as a basis for obtaining promising medicinal agents (primarily, for boron neutron capture therapy), as well as for design the materials with unique properties. For the first time, this review summarizes and analyzes information on the methods of preparation and possible applications of compounds combining in their structure amino acid and peptide residues and carborane clusters, their biological and physicochemical properties. Special attention is paid to the preparation of enantiopure conjugates, the chirality of which is due to both the presence of an asymmetric carbon atom in amino acid fragments and the planar chirality of the carborane cluster. We believe that this review provides comprehensive information about carborane-containing amino acids and peptides and will give a new impetus to the in-depth fundamental research in this field.