ArticleJournal of the American Chemical Society2017
Synthesis and Deployment of an Elusive Fluorovinyl Cation Equivalent: Access to Quaternary α-(1'-Fluoro)vinyl Amino Acids as Potential PLP Enzyme Inactivators.
Article in Journal of the American Chemical Society, 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 16 papers.
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Who cites it
16 citing papers in PubMed, 55 citations in OpenAlex.
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- Targeting Conformational Flexibility of a Reactive Intermediate to Enhance Selectivity of a GABA Aminotransferase Inactivator.Journal of the American Chemical Society · 2026Article
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- Biomacromolecule-Assisted Screening for Reaction Discovery and Catalyst Optimization.Chemical reviews · 2022Review
- Synthesis of bioactive fluoropyrrolidinesChemical science · 2022Article
- Modification of N-terminal α-amine of proteins via biomimetic ortho-quinone-mediated oxidation.Nature communications · 2021Article
- Structural and functional analysis of the Francisella lysine decarboxylase as a key actor in oxidative stress resistance.Scientific reports · 2021Article
- Cobalt-Catalyzed Selective Unsymmetrical Dioxidation ofThe Journal of organic chemistry · 2020Article
- Mechanism of Inactivation of Ornithine Aminotransferase by (1Journal of the American Chemical Society · 2019Article
- Copper-Catalyzed Regioselective Synthesis of (Molecules (Basel, Switzerland) · 2019Article
- Article
- Use of trifluoroacetaldehyde N-tfsylhydrazone as a trifluorodiazoethane surrogate and its synthetic applications.Nature communications · 2019Article
- Human Serine Racemase: Key Residues/Active Site Motifs and Their Relation to Enzyme Function.Frontiers in molecular biosciences · 2019Review
- Design and Mechanism of GABA Aminotransferase Inactivators. Treatments for Epilepsies and Addictions.Chemical reviews · 2018Review
- A thiocyanopalladation/carbocyclization transformation identified through enzymatic screening: stereocontrolled tandem C-SCN and C-C bond formation.Chemical science · 2017Article
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Authors and funding
6 authors at 1 institution in 1 country.
Funding
Abstract
Developing specific chemical functionalities to deploy in biological environments for targeted enzyme inactivation lies at the heart of mechanism-based inhibitor development but also is central to other protein-tagging methods in modern chemical biology including activity-based protein profiling and proteolysis-targeting chimeras. We describe here a previously unknown class of potential PLP enzyme inactivators; namely, a family of quaternary, α-(1'-fluoro)vinyl amino acids, bearing the side chains of the cognate amino acids. These are obtained by the capture of suitably protected amino acid enolates with β,β-difluorovinyl phenyl sulfone, a new (1'-fluoro)vinyl cation equivalent, and an electrophile that previously eluded synthesis, capture and characterization. A significant variety of biologically relevant AA side chains are tolerated including those for alanine, valine, leucine, methionine, lysine, phenylalanine, tyrosine, and tryptophan. Following addition/elimination, the resulting transoid α-(1'-fluoro)-β-(phenylsulfonyl)vinyl AA-esters undergo smooth sulfone-stannane interchange to stereoselectively give the corresponding transoid α-(1'-fluoro)-β-(tributylstannyl)vinyl AA-esters. Protodestannylation and global deprotection then yield these sterically encumbered and densely functionalized quaternary amino acids. The α-(1'-fluoro)vinyl trigger, a potential allene-generating functionality originally proposed by Abeles, is now available in a quaternary AA context for the first time. In an initial test of this new inhibitor class, α-(1'-fluoro)vinyllysine is seen to act as a time-dependent, irreversible inactivator of lysine decarboxylase from Hafnia alvei. The enantiomers of the inhibitor could be resolved, and each is seen to give time-dependent inactivation with this enzyme. Kitz-Wilson analysis reveals similar inactivation parameters for the two antipodes, L-α-(1'-fluoro)vinyllysine (K
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