ArticleAngewandte Chemie (International ed. in English)2019
Chemoenzymatic Platform for Synthesis of Chiral Organofluorines Based on Type II Aldolases.
Article in Angewandte Chemie (International ed. in English), 2019. 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.
- To PLP or Not to PLP: Stereodivergent Transaminase-Catalyzed Reactions Directed by Kinetic and Thermodynamic Control.The Journal of organic chemistry · 2025Article
- Photoenzymatic enantioselective synthesis of fluorinated amides with remote stereocenter.Nature communications · 2025Article
- Ground-state flavin-dependent enzymes catalyzed enantioselective radical trifluoromethylation.Nature communications · 2025Article
- The metal cofactor: stationary or mobile?Applied microbiology and biotechnology · 2024Review
- Fluorinated building blocks in drug design: new pathways and targets.Future medicinal chemistry · 2024Article
- Substrate Induced Movement of the Metal Cofactor between Active and Resting State.Angewandte Chemie (International ed. in English) · 2022Article
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- NewChemical science · 2022Article
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- Natural and Synthetic Halogenated Amino Acids-Structural and Bioactive Features in Antimicrobial Peptides and Peptidomimetics.Molecules (Basel, Switzerland) · 2021Review
- Enzymatic synthesis of fluorinated compounds.Applied microbiology and biotechnology · 2021Review
- Recent trends in the stereoselective synthesis of (poly)-substituted 2-oxo acids by biocatalyzed aldol reaction.Current opinion in green and sustainable chemistry · 2021Article
- Chemoenzymatic Production of Enantiocomplementary 2-Substituted 3-Hydroxycarboxylic Acids from L-α-Amino Acids.Advanced synthesis & catalysis · 2021Article
- Progress in Stereoselective Construction of C-C Bonds Enabled by Aldolases and Hydroxynitrile Lyases.Frontiers in bioengineering and biotechnology · 2021Review
- Identification of 5-Fluoro-5-Deoxy-Ribulose as a Shunt Fluorometabolite inBiomolecules · 2020Article
- Chemoenzymatic Synthesis and Biological Evaluation for Bioactive Molecules Derived from Bacterial Benzoyl Coenzyme A Ligase and Plant Type III Polyketide Synthase.Biomolecules · 2020Article
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4 authors.
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Abstract
Aldolases are C-C bond forming enzymes that have become prominent tools for sustainable synthesis of complex synthons. However, enzymatic methods of fluorine incorporation into such compounds are lacking due to the rarity of fluorine in nature. Recently, the use of fluoropyruvate as a non-native aldolase substrate has arisen as a solution. Here, we report that the type II HpcH aldolases efficiently catalyze fluoropyruvate addition to diverse aldehydes, with exclusive (3S)-selectivity at fluorine that is rationalized by DFT calculations on a mechanistic model. We also measure the kinetic parameters of aldol addition and demonstrate engineering of the hydroxyl group stereoselectivity. Our aldolase collection is then employed in the chemoenzymatic synthesis of novel fluoroacids and ester derivatives in high stereopurity (d.r. 80-98 %). The compounds made available by this method serve as precursors to fluorinated analogs of sugars, amino acids, and other valuable chiral building blocks.
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