Synthesis of 2-amino-3-fluoroacrylic acid containing peptides.
[reaction: see text] Peptides containing (E)- and (Z)-3-fluorodehydroalanine have been prepared from serine via a fluoro-Pummerer rearrangement. The resulting electrophilic moieties may be useful affinity labels for the identification of the targets of dehydroamino acid containing natural products that act by covalent mechanisms.
Zhou
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Department of Chemistry, University of Illinois at Urbana-Champaign, 61801, USA.
van der Donk
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WA
D000179:Acrylates / Q000138:chemical synthesis* / Q000737:chemistry; D000409:Alanine / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000737:chemistry; D004151:Dipeptides / Q000138:chemical synthesis* / Q000737:chemistry; D005461:Fluorine / Q000737:chemistry; D015394:Molecular Structure; D012694:Serine / Q000737:chemistry
C423583:2-amino-3-fluoroacrylic acid; C423584:3-fluorodehydroalanine; D000179:Acrylates; D004151:Dipeptides; D005461:Fluorine; D012694:Serine; D000409:Alanine