ArticleJournal of the American Chemical Society2020
Stereoselective and Divergent Construction of β-Thiolated/Selenolated Amino Acids via Photoredox-Catalyzed Asymmetric Giese Reaction.
Article in Journal of the American Chemical Society, 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 23 papers.
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Who cites it
23 citing papers in PubMed.
- 4-Formyl-N-Methylpyridinium-Mediated N-Terminal Cysteine Modification/Removal Facilitates One-Pot Multiplex Peptide Ligation.Angewandte Chemie (International ed. in English) · 2026Article
- Synthesis of β-Thiolated Amino Acids: Investigation Toward the Total Chemical Synthesis of Lasso Peptide Microcin J25.Chembiochem : a European journal of chemical biology · 2026Article
- Copper-Catalyzed Enantioselective Synthesis of Chiral Selenium-Based Versatile Synthons.ACS central science · 2026Article
- Pyridium-π interaction preserves N,S-benzylidene thioacetals in acidolysis enabling efficient protein chemical synthesis.Nature communications · 2026Article
- Discovery of Unprecedented Arylation Coupling Cyclopeptide Inspires Natural Product-like Antitubercular Lead Compounds.JACS Au · 2025Article
- Divergent Synthesis of ΔAA-Peptides Using a Bioorthogonal pro-Amino Acid and Aqueous Flavin Photocatalyst: Green Light Enhances Catalyst Performance and Product Selectivity.Angewandte Chemie (International ed. in English) · 2025Article
- Advances in the chemical synthesis of human proteoforms.Science China. Life sciences · 2025Review
- Complexity of the Hypothalamic Oxytocin System and its Involvement in Brain Functions and Diseases.Neuroscience bulletin · 2025Review
- Concise Syntheses of Lycojapomine Alkaloids Enabled by Radical Dearomatization of a Pyrrole.Journal of the American Chemical Society · 2025Article
- Production of constrained L-cyclo-tetrapeptides by epimerization-resistant direct aminolysis.Nature communications · 2024Article
- Simplified Modular Access to Enantiopure 1,2-Aminoalcohols via Ni-Electrocatalytic Decarboxylative Arylation.Journal of the American Chemical Society · 2024Article
- Selenium chemistry for spatio-selective peptide and protein functionalization.Nature reviews. Chemistry · 2024Review
- Stereoselective alkylChemical science · 2023Article
- Intertwined associations between oxytocin, immune system and major depressive disorder.Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie · 2023Review
- Towards Enantiomerically Pure Unnatural α-Amino Acids via Photoredox Catalytic 1,4-Additions to a Chiral Dehydroalanine.The Journal of organic chemistry · 2022Article
- carba-Nucleopeptides (cNPs): A Biopharmaceutical Modality Formed through Aqueous Rhodamine B Photoredox Catalysis.Angewandte Chemie (International ed. in English) · 2022Article
- Visible-light-mediated catalyst-free synthesis of unnatural α-amino acids and peptide macrocycles.Nature communications · 2021Article
- Recent Advances in Photoredox-Mediated Radical Conjugate Addition Reactions: An Expanding Toolkit for the Giese Reaction.Angewandte Chemie (International ed. in English) · 2021Review
- Rapid one-pot iterative diselenide-selenoester ligation using a novel coumarin-based photolabile protecting group.Chemical science · 2021Article
- Synthetic Homogeneous Glycoforms of the SARS-CoV-2 Spike Receptor-Binding Domain Reveals Different Binding Profiles of Monoclonal Antibodies.Angewandte Chemie (International ed. in English) · 2021Article
Corrections and comments
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Authors and funding
7 authors.
Funding
Abstract
Sulfur and selenium occupy a distinguished position in biology owing to their redox activities, high nucleophilicity, and acyl transfer capabilities. Thiolated/selenolated amino acids, including cysteine, selenocysteine, and their derivatives, play critical roles in regulating the conformation and function of proteins and serve as an important motif for peptide design and bioconjugation. Unfortunately, a general and concise method to attain enantiopure β-thiolated/selenolated amino acids remains an unsolved problem. Herein, we present a photoredox-catalyzed asymmetric method for the preparation of enantiopure β-thiolated/selenolated amino acids using a simple chiral auxiliary, which controls the diastereoselectivity of the key alkylation step and acts as an orthogonal protecting group in the subsequent peptide synthesis. Our protocol can be used to prepare a wide range of β-thiolated/selenolated amino acids on a gram scale, which would otherwise be difficult to obtain using conventional methods. The effect of our chemistry was further highlighted and validated through the preparation of a series of peptidyl thiol/selenol analogues, including cytochrome
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