ArticleJournal of the American Chemical Society2024
Enzymatic Synthesis of Unprotected α,β-Diamino Acids via Direct Asymmetric Mannich Reactions.
Article in Journal of the American Chemical Society, 2024. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 10 papers.
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Who cites it
10 citing papers in PubMed.
- A pyridoxal phosphate-dependent enzyme platform for stereoselective synthesis of γ-tertiary-nitro-noncanonical amino acids.Nature communications · 2026Article
- Asymmetric Iron-Catalyzed Vicinal C(spAngewandte Chemie (International ed. in English) · 2026Article
- Promiscuity-Guided Enzyme Evolution via Substrate Multiplexed Screening.Angewandte Chemie (International ed. in English) · 2026Review
- Emerging enzymatic strategies for the synthesis of α-tertiary amino acids.Communications chemistry · 2026Review
- Intracellular assembly of artificial enzymes for cytoplasmic enantioselective Mannich reactions.Nature communications · 2026Article
- Kinetic resolution of amino acids by phosphine oxide catalyzed enantioselective esterification.Nature communications · 2026Article
- Pyridoxal 5'-Phosphate-Dependent Enzymatic Decarboxylative Annulation.Journal of the American Chemical Society · 2026Article
- Active site diversification of a non-canonical amino acid decarboxylase by merging substrate multiplexed screening with computationally guided recombination.Protein science : a publication of the Protein Society · 2025Article
- Accessing acyclic vicinal tetrasubstituted stereocenters via biomimetic Cu/squaramide cooperative catalysed asymmetric Mannich reactions.Nature communications · 2025Article
- Engineering a PLP-dependent Mannichase.Methods in enzymology · 2025Article
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4 authors.
Funding
Abstract
α,β-Diamino acids are important structural motifs and building blocks for numerous bioactive natural products, peptidomimetics, and pharmaceuticals, yet efficient asymmetric synthesis to access these stereoarrays remains a challenge. Herein, we report the development of a pyridoxal 5'-phosphate (PLP)-dependent enzyme that is engineered to catalyze stereoselective Mannich-type reactions between free α-amino acids and enolizable cyclic imines. This biocatalyst enabled one-step asymmetric enzymatic synthesis of the unusual pyrrolidine-containing amino acid L-tambroline at gram-scale with high enantio- and diastereocontrol. Furthermore, this enzymatic platform is capable of utilizing a diverse range of α-amino acids as the Mannich donor and various cyclic imines as the acceptor. By coupling with different imine-generating enzymes, we established versatile biocatalytic cascades and demonstrated a general, concise, versatile, and atom-economic approach to access unprotected α,β-diamino acids, including structurally complex α,α-disubstituted α,β-diamino acids with contiguous stereocenters.
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