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Improved enantioselective gram scale synthesis route to N-Fmoc-protected monofluoroethylglycine

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Abstract Fluorine, as a substituent in amino acids, has found its way into peptide and protein engineering. The basis for the use of this valuable tool is the synthetic accessibility… Click to show full abstract

Abstract Fluorine, as a substituent in amino acids, has found its way into peptide and protein engineering. The basis for the use of this valuable tool is the synthetic accessibility of various fluorinated amino acids as building blocks of peptides and proteins. In this context, we present a straightforward eight-step synthesis of N-Fmoc- l -monofluoroethylglycine (MfeGly) via homoserine (Hse) as intermediate and using various nucleophilic fluorination strategies.

Keywords: gram scale; fmoc; enantioselective gram; monofluoroethylglycine; synthesis; improved enantioselective

Journal Title: Journal of Fluorine Chemistry
Year Published: 2020

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