Abstract
[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.
Publication types
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Research Support, Non-U.S. Gov't
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Research Support, U.S. Gov't, Non-P.H.S.
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Research Support, U.S. Gov't, P.H.S.
MeSH terms
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Acrylates / chemical synthesis*
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Acrylates / chemistry
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Alanine / analogs & derivatives
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Alanine / chemical synthesis*
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Alanine / chemistry
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Dipeptides / chemical synthesis*
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Dipeptides / chemistry
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Fluorine / chemistry
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Molecular Structure
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Serine / chemistry
Substances
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2-amino-3-fluoroacrylic acid
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3-fluorodehydroalanine
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Acrylates
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Dipeptides
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Fluorine
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Serine
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Alanine