Enantioselective Synthesis of N-Substituted Aspartic Acids Using an Engineered Variant of Methylaspartate Ammonia Lyase

Authors

  • Dr. Vinod Puthan Veetil,

    1. Department of Pharmaceutical Biology, Groningen Research Institute of Pharmacy, University of Groningen, Antonius Deusinglaan 1, 9713 AV Groningen (The Netherlands)
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    • These authors contributed equally to this work.

  • Hans Raj,

    1. Department of Pharmaceutical Biology, Groningen Research Institute of Pharmacy, University of Groningen, Antonius Deusinglaan 1, 9713 AV Groningen (The Netherlands)
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    • These authors contributed equally to this work.

  • Dr. Marianne de Villiers,

    1. Department of Pharmaceutical Biology, Groningen Research Institute of Pharmacy, University of Groningen, Antonius Deusinglaan 1, 9713 AV Groningen (The Netherlands)
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  • Pieter G. Tepper,

    1. Department of Pharmaceutical Biology, Groningen Research Institute of Pharmacy, University of Groningen, Antonius Deusinglaan 1, 9713 AV Groningen (The Netherlands)
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  • Prof. Dr. Frank J. Dekker,

    1. Department of Pharmaceutical Gene Modulation, Groningen Research Institute of Pharmacy, University of Groningen, Antonius Deusinglaan 1, 9713 AV Groningen (The Netherlands)
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  • Prof. Dr. Wim J. Quax,

    1. Department of Pharmaceutical Biology, Groningen Research Institute of Pharmacy, University of Groningen, Antonius Deusinglaan 1, 9713 AV Groningen (The Netherlands)
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  • Prof. Dr. Gerrit J. Poelarends

    Corresponding author
    1. Department of Pharmaceutical Biology, Groningen Research Institute of Pharmacy, University of Groningen, Antonius Deusinglaan 1, 9713 AV Groningen (The Netherlands)
    • Department of Pharmaceutical Biology, Groningen Research Institute of Pharmacy, University of Groningen, Antonius Deusinglaan 1, 9713 AV Groningen (The Netherlands)
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Abstract

original image

Unnatural reactions: We report the synthesis of a large variety of N-substituted aspartic acids by addition of structurally diverse amines to fumaric acid; the reactions are catalyzed by a previously engineered variant of methylaspartate ammonia lyase. The additions are highly enantioselective and yield only the L enantiomers of the corresponding amino acid products (>99 % ee).

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