ArticleNature communications2024
Direct asymmetric synthesis of β-branched aromatic α-amino acids using engineered phenylalanine ammonia lyases.
Article in Nature communications, 2024. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 9 papers.
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Who cites it
9 citing papers in PubMed.
- MutexaGPT: An Intuition-to-Design Translator for Physics-based Enzyme Engineering.Research square · 2026Article
- Engineering ω-transaminase for efficient dihydroxyacetone transamination in serinol biosynthesis starting from methanol.Synthetic and systems biotechnology · 2026Article
- Nickel-Photocatalytic Deoxygenative Arylation toward β-Methyl-Branched α-Amino Acids.Organic letters · 2026Article
- ASH: A Multi-Scale, Multi-Theory Modeling Program.Journal of computational chemistry · 2026Article
- Concise construction of β-branched aromatic D-amino acids via transaminase-catalyzed dynamic kinetic resolution.Nature communications · 2026Article
- Biocatalytic Synthesis of N-Protected α-Amino Acids through 1,3-Nitrogen Migration by Nonheme Iron Enzymes.Journal of the American Chemical Society · 2025Article
- A Self-Sufficient β-Methylarginine Biosynthetic Pathway in Planctomycetes.Chembiochem : a European journal of chemical biology · 2025Article
- An Update: Enzymatic Synthesis for Industrial Applications.Angewandte Chemie (International ed. in English) · 2025Review
- Engineered Biocatalysts for the Asymmetric Synthesis of d-Phenylalanines.ACS catalysis · 2025Review
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13 authors.
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Abstract
β-Branched aromatic α-amino acids are valuable building blocks in natural products and pharmaceutically active compounds. However, their chemical or enzymatic synthesis is challenging due to the presence of two stereocenters. We design phenylalanine ammonia lyases (PAL) variants for the direct asymmetric synthesis of β-branched aromatic α-amino acids. Based on extensive computational analyses, we unravel the enigma behind PAL's inability to accept β-methyl cinnamic acid (β-MeCA) as substrate and achieve the synthesis of the corresponding amino acids of β-MeCA and analogs using a double (PcPAL-L256V-I460V) and a triple mutant (PcPAL-F137V-L256V-I460V). The reactions are scaled-up using an optimized E. coli based whole-cell biotransformation system to produce ten β-branched phenylalanine analogs with high diastereoselectivity (dr > 20:1) and enantioselectivity (ee > 99.5%) in yields ranging from 41-71%. Moreover, we decipher the mechanism of PcPAL-L256V-I460V for the acceptance of β-MeCA and converting it with excellent stereoselectivity by computational simulations. Thus, this study offers an efficient method for synthesizing β-branched aromatic α-amino acids.
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