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Synfacts 2020; 16(08): 0992
DOI: 10.1055/s-0040-1707445
DOI: 10.1055/s-0040-1707445
Peptide Chemistry
Synthesis of Fluorodehydroalanine-Containing Peptides
Weitere Informationen
Publikationsverlauf
Publikationsdatum:
21. Juli 2020 (online)
Key words
dehydroalanine - aminofluoroacrylates - fluoro-Pummerer rearrangement - fluorodehydroalanineSignificance
Dehydroalanine moieties occur abundantly as scaffolds in natural products. Also, fluorine-substituted compounds have received increasing attention due to their small steric bulk and their lipophilicity. The authors developed a strategy for the synthesis of fluorine-substituted dehydroalanines.
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Comment
(E)- And (Z)-fluorodehydroalanines were synthesized from N-protected serines through a fluoro-Pummerer rearrangement. Moreover, this methodology can be applied in dipeptide synthesis.
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