ChemInform Abstract: Asymmetric Synthesis of Fluorine‐Containing Amino Acids

Abstract

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Exploration of Fluorine Chemistry at the Multidisciplinary Interface of Chemistry and Biology

“…103–107 Because of the unique properties of fluorine as element, the introduction of fluorine(s), CF 2 H, or CF 3 group to biologically active molecules often critically improves their pharmacological properties. 19,103 Moreover, the sensitivity of 19 F NMR spectroscopy along with large 19 F- 1 H coupling constants and the virtual absence of 19 F in the living tissue render fluorine incorporation a particularly powerful tool for the investigation of biological processes. 8,108,109 Therefore, fluorine-containing α-hydroxy-β-amino acids are expected to serve as useful bioactive compounds with a wide range of potential applications in medicinal chemistry and chemical biology.…”

“…However, only a few methods had been reported for the synthesis of fluorine-containing α-hydroxy-β-amino acids when we started our investigation in mid-late 1990s. 19,110–114 …”

“…11–19 The limited availability of fluoro-chemicals for bioorganic and medicinal chemistry as well as pharmaceutical and agrochemical applications is mainly due to the exceptional properties and hazardous nature of fluorine and fluoro-chemical sources. Also, in many cases, synthetic methods developed for ordinary organic molecules do not work well for fluoro-chemicals because of their unique reactivity.…”

“…Also, in many cases, synthetic methods developed for ordinary organic molecules do not work well for fluoro-chemicals because of their unique reactivity. 11–19 Therefore, the new and efficient synthetic methods applicable to organofluorine compounds, including 18 F radiotracers, need to be continuously developed.…”

Advances in the chemistry of ?-lactam and its medicinal applications

“…43,97,98 As fluorine is absent in living tissue, the incorporation of fluorine(s) into biologically relevant molecules as marker(s) provides a valuable means to monitor protein structures and dynamics as well as drug-protein interactions in vitro and in vivo by 19 F NMR. Accordingly, efficient and convenient methods for the synthesis of fluorine-containing compounds of biological and medical interest are in high demand.…”