ReviewOrganic & biomolecular chemistry2019
Dehydroamino acids: chemical multi-tools for late-stage diversification.
Review in Organic & biomolecular chemistry, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 35 papers.
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Who cites it
35 citing papers in PubMed, 112 citations in OpenAlex.
- α,β-Dehydroamino-Acid-Containing Peptides Resist Proteolysis and Inhibit Aggregation of a Tau-Derived Model Peptide.The Journal of organic chemistry · 2026Article
- Cobalt-catalyzed alkyne silylamidation unlocksNational science review · 2026Article
- Late-Stage Aromatic C-H Bond Functionalization for Cysteine/Selenocysteine Bioconjugation.Journal of the American Chemical Society · 2025Article
- Catalytic Markovnikov Hydrothiolation of Dehydroamino Acids: Unified Total Synthesis of Enteropeptin Sactipeptides.Journal of the American Chemical Society · 2025Article
- Late-Stage N-Alkenylative Modifications of Indolic Scaffolds with Propiolates: Toward Bisconjugation and Macrocyclization.Organic letters · 2025Article
- Ligand-Enabled Selective Coupling of MIDA Boronates to Dehydroalanine-Containing Peptides and Proteins.Journal of the American Chemical Society · 2025Article
- Poly-Dha Sequences asJACS Au · 2024Article
- Article
- Mechanism of Abnormal Activation of MEK1 Induced by Dehydroalanine Modification.International journal of molecular sciences · 2024Article
- Enantioselective organocatalytic strategies to access noncanonical α-amino acids.Chemical science · 2024Review
- A Compact Reprogrammed Genetic Code for De Novo Discovery of Proteolytically Stable Thiopeptides.Journal of the American Chemical Society · 2024Article
- Dehydroamino acid residues in bioactive natural products.Natural product reports · 2024Review
- α,β-Dehydroamino Acid Synthesis through Proline-Catalyzed Aldol Condensation with a Glycine Schiff Base.Precision chemistry · 2024Article
- Giese-type alkylation of dehydroalanine derivatives via silane-mediated alkyl bromide activation.Beilstein journal of organic chemistry · 2024Article
- Iron-Catalyzed Synthesis of α-Azido α-Amino Esters via the Alkylazidation of Alkenes.Organic letters · 2023Article
- Light-initiated 1,3-dipolar cycloaddition between dehydroalanines and tetrazoles: application to late-stage peptide and protein modifications.Chemical science · 2023Article
- Carbon-Centered Radicals in Protein Manipulation.ACS central science · 2023Review
- The mechanism of thia-Michael addition catalyzed by LanC enzymes.Proceedings of the National Academy of Sciences of the United States of America · 2023Article
- Molecular flavin catalysts for C-H functionalisation and derivatisation of dehydroamino acids.Chemical science · 2022Article
- PeptideACS central science · 2022Article
Corrections and comments
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Authors and funding
2 authors at 1 institution in 2 countries.
Funding
Abstract
α,β-Dehydroamino acids (dhAAs) are noncanonical amino acids that are found in a wide array of natural products and can be easily installed into peptides and proteins. dhAAs exhibit remarkable synthetic flexibility, readily undergoing a number of reactions, such as polar and single-electron additions, transition metal catalyzed cross-couplings, and cycloadditions. Because of the relatively mild conditions required for many of these reactions, dhAAs are increasingly being used as orthogonal chemical handles for late-stage modification of biomolecules. Still, only a fraction of the chemical reactivity of dhAAs has been exploited in such biorthogonal applications. Herein, we provide an overview of the broad spectrum of chemical reactivity of dhAAs, with special emphasis on recent efforts to adapt such transformations for biomolecules such as natural products, peptides, and proteins. We also discuss examples of enzymes from natural product biosynthetic pathways that have been found to catalyze many similar reactions; these enzymes provide mild, regio- and stereoselective, biocatalytic alternatives for future development. We anticipate that the continued investigation of the innate reactivity of dhAAs will furnish a diverse portfolio dhAA-based chemistries for use in chemical biology and drug discovery.
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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.