ArticleACS central science2016
Anion-π Enzymes.
Article in ACS central science, 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 20 papers.
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Who cites it
20 citing papers in PubMed.
- Unveiling the alkyne-π interaction using metal-organic cage compounds.Communications chemistry · 2025Article
- The Realm of Unconventional Noncovalent Interactions in Proteins: Their Significance in Structure and Function.ACS omega · 2023Review
- Going Full Circle with Organocatalysis and Biocatalysis: The Latent Potential of Cofactor Mimics in Asymmetric Synthesis.The Journal of organic chemistry · 2023Review
- Anion-π catalysis on carbon allotropes.Beilstein journal of organic chemistry · 2023Review
- Occurrence and stability of anion-π interactions between phosphate and nucleobases in functional RNA molecules.Nucleic acids research · 2022Article
- Derivatives of Natural Organocatalytic Cofactors and Artificial Organocatalytic Cofactors as Catalysts in Enzymes.Chembiochem : a European journal of chemical biology · 2022Review
- Mining anion-aromatic interactions in the Protein Data Bank.Chemical science · 2022Article
- Anion-π Catalysis Enabled by the Mechanical Bond.Angewandte Chemie (International ed. in English) · 2022Article
- The role of streptavidin and its variants in catalysis by biotinylated secondary amines.Organic & biomolecular chemistry · 2021Article
- Transfer hydrogenations catalyzed by streptavidin-hosted secondary amine organocatalysts.Chemical communications (Cambridge, England) · 2021Article
- Streptavidin-Hosted Organocatalytic Aldol Addition.Molecules (Basel, Switzerland) · 2020Article
- Enabling protein-hosted organocatalytic transformations.RSC advances · 2020Review
- Cyclic di-AMP, a second messenger of primary importance: tertiary structures and binding mechanisms.Nucleic acids research · 2020Review
- Breaking Symmetry: Engineering Single-Chain Dimeric Streptavidin as Host for Artificial Metalloenzymes.Journal of the American Chemical Society · 2019Article
- Streptavidin interfacing as a general strategy to localize fluorescent membrane tension probes in cells.Chemical science · 2019Article
- Reactivity and Selectivity of Iminium Organocatalysis Improved by a Protein Host.Angewandte Chemie (International ed. in English) · 2018Article
- Remote Control of Anion-π Catalysis on Fullerene-Centered Catalytic Triads.Angewandte Chemie (International ed. in English) · 2018Article
- Catalysis with Pnictogen, Chalcogen, and Halogen Bonds.Angewandte Chemie (International ed. in English) · 2018Article
- Catalysis with chalcogen bonds: neutral benzodiselenazole scaffolds with high-precision selenium donors of variable strength.Chemical science · 2017Article
- Anion-π catalysis: bicyclic products with four contiguous stereogenic centers from otherwise elusive diastereospecific domino reactions on π-acidic surfaces.Chemical science · 2017Article
Corrections and comments
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Authors and funding
5 authors.
Funding
No grant is acknowledged in the PubMed record.
Abstract
In this report, we introduce artificial enzymes that operate with anion-π interactions, an interaction that is essentially new to nature. The possibility to stabilize anionic intermediates and transition states on an π-acidic surface has been recently demonstrated, using the addition of malonate half thioesters to enolate acceptors as a biologically relevant example. The best chiral anion-π catalysts operate with an addition/decarboxylation ratio of 4:1, but without any stereoselectivity. To catalyze this important but intrinsically disfavored reaction stereoselectively, a series of anion-π catalysts was equipped with biotin and screened against a collection of streptavidin mutants. With the best hit, the S112Y mutant, the reaction occurred with 95% ee and complete suppression of the intrinsically favored side product from decarboxylation. This performance of anion-π enzymes rivals, if not exceeds, that of the best conventional organocatalysts. Inhibition of the S112Y mutant by nitrate but not by bulky anions supports that contributions from anion-π interactions exist and matter, also within proteins. In agreement with docking results, K121 is shown to be essential, presumably to lower the pK a of the tertiary amine catalyst to operate at the optimum pH around 3, that is below the pK a of the substrate. Most importantly, increasing enantioselectivity with different mutants always coincides with increasing rates and conversion, i.e., selective transition-state stabilization.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.