SYNTHESIS OF TAILOR-MADE AMINO ACIDS CONTAINING C(sp2)–F BONDS
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...
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| Дата: | 2025 |
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| Автори: | , , , , , , |
| Формат: | Стаття |
| Мова: | English |
| Опубліковано: |
V.I.Vernadsky Institute of General and Inorganic Chemistry
2025
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| Онлайн доступ: | https://ucj.org.ua/index.php/journal/article/view/745 |
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| Назва журналу: | Ukrainian Chemistry Journal |
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oai:ojs2.1444248.nisspano.web.hosting-test.net:article-7452025-11-25T14:50:50Z SYNTHESIS OF TAILOR-MADE AMINO ACIDS CONTAINING C(sp2)–F BONDS Wzorek, Alicja Han, Jianlin Ono, Taizo Klika, Karel Baecker, Daniel Zhang, Wei Soloshonok, Vadim Fluorine, Amino Acids, Fluorinated Pharmaceuticals, Unsaturated/Olefinic Groups, Synthesis, Nucleophilic and Electrophilic Glycine Equivalents. 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. V.I.Vernadsky Institute of General and Inorganic Chemistry 2025-09-25 Article Article Organic chemistry Органическая xимия Органічна xімія application/pdf https://ucj.org.ua/index.php/journal/article/view/745 10.33609/2708-129X.91.8.2025.36-64 Ukrainian Chemistry Journal; Vol. 91 No. 8 (2025): Ukrainian Chemistry Journal; 36-64 Украинский химический журнал; Том 91 № 8 (2025): Ukrainian Chemistry Journal; 36-64 Український хімічний журнал; Том 91 № 8 (2025): Ukrainian Chemistry Journal; 36-64 2708-129X 2708-1281 en https://ucj.org.ua/index.php/journal/article/view/745/382 |
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Ukrainian Chemistry Journal |
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| datestamp_date |
2025-11-25T14:50:50Z |
| collection |
OJS |
| language |
English |
| topic_facet |
Fluorine Amino Acids Fluorinated Pharmaceuticals Unsaturated/Olefinic Groups Synthesis Nucleophilic and Electrophilic Glycine Equivalents. |
| format |
Article |
| author |
Wzorek, Alicja Han, Jianlin Ono, Taizo Klika, Karel Baecker, Daniel Zhang, Wei Soloshonok, Vadim |
| spellingShingle |
Wzorek, Alicja Han, Jianlin Ono, Taizo Klika, Karel Baecker, Daniel Zhang, Wei Soloshonok, Vadim SYNTHESIS OF TAILOR-MADE AMINO ACIDS CONTAINING C(sp2)–F BONDS |
| author_facet |
Wzorek, Alicja Han, Jianlin Ono, Taizo Klika, Karel Baecker, Daniel Zhang, Wei Soloshonok, Vadim |
| author_sort |
Wzorek, Alicja |
| title |
SYNTHESIS OF TAILOR-MADE AMINO ACIDS CONTAINING C(sp2)–F BONDS |
| title_short |
SYNTHESIS OF TAILOR-MADE AMINO ACIDS CONTAINING C(sp2)–F BONDS |
| title_full |
SYNTHESIS OF TAILOR-MADE AMINO ACIDS CONTAINING C(sp2)–F BONDS |
| title_fullStr |
SYNTHESIS OF TAILOR-MADE AMINO ACIDS CONTAINING C(sp2)–F BONDS |
| title_full_unstemmed |
SYNTHESIS OF TAILOR-MADE AMINO ACIDS CONTAINING C(sp2)–F BONDS |
| title_sort |
synthesis of tailor-made amino acids containing c(sp2)–f bonds |
| description |
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. |
| publisher |
V.I.Vernadsky Institute of General and Inorganic Chemistry |
| publishDate |
2025 |
| url |
https://ucj.org.ua/index.php/journal/article/view/745 |
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2025-12-02T15:13:46Z |
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2025-12-02T15:13:46Z |
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