SYNTHESIS OF TAILOR-MADE AMINO ACIDS CONTAINING C(sp2)–F BONDS

• Дата: 2025
• Автори: Wzorek, Alicja, Han, Jianlin, Ono, Taizo, Klika, Karel, Baecker, Daniel, Zhang, Wei, Soloshonok, Vadim
• Формат: Стаття
• Мова: English
• Опубліковано: V.I.Vernadsky Institute of General and Inorganic Chemistry 2025
• Онлайн доступ: https://ucj.org.ua/index.php/journal/article/view/745
• Назва журналу: Ukrainian Chemistry Journal

Amino acids are fundamental to virtually every aspect of biological science and healthcare ser­ving as the cornerstone of molecular structure and function. Research has now expanded beyond naturally occurring amino acids to tailor-made derivatives enabling precise control over biological pro­cesses and unlocking new functionalities unattainable with standard amino acids and peptides. One of the most exciting advancements is the development of fluorine-containing amino acids which integrate the powerful pharmacological effects of fluorine with the structural adaptability of amino acid frameworks. This review explores the synthesis of fluorinated amino acids bearing unsaturated residues—a highly valuable and distinct subgroup within the broader class of fluorinated amino acids. These specialized molecules feature fluorine directly bonded to sp2-hybridized carbon atoms, effectively replicating the electronic properties of aromatic substitution without relying on an aromatic system. The olefinic placement of fluorine enhances molecular stability and imparts specific steric, geometric, chemical, and biological characteristics critical for drug design and bioactive compound development. The synthetic strategies presented herein are organized around key transformations, including α alkylation of amino acids, side chain elaboration, introduction of amino and/or carboxylic functionalities, and the generation of unsaturation within fluoro-amino acid cores. By compiling these methodologies we aim to provide a comprehensive resource and a source of inspiration for researchers engaged in synthetic and medicinal chemistry, drug discovery, and organofluorine chemistry.