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Synthesis of β-Branched Tryptophan Analogues Using an Engineered Subunit of Tryptophan Synthase

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    Synthesis of β-Branched Tryptophan Analogues Using an Engineered Subunit of Tryptophan Synthase
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    Division of Chemistry and Chemical Engineering 210-41, California Institute of Technology, 1200 East California Boulevard, Pasadena, California 91125, United States
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    Cite this: J. Am. Chem. Soc. 2016, 138, 27, 8388–8391
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    https://doi.org/10.1021/jacs.6b04836
    Published June 29, 2016
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    Abstract

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    We report that l-threonine may substitute for l-serine in the β-substitution reaction of an engineered subunit of tryptophan synthase from Pyrococcus furiosus, yielding (2S,3S)-β-methyltryptophan (β-MeTrp) in a single step. The trace activity of the wild-type β-subunit on this substrate was enhanced more than 1000-fold by directed evolution. Structural and spectroscopic data indicate that this increase is correlated with stabilization of the electrophilic aminoacrylate intermediate. The engineered biocatalyst also reacts with a variety of indole analogues and thiophenol for diastereoselective C–C, C–N, and C–S bond-forming reactions. This new activity circumvents the 3-enzyme pathway that produces β-MeTrp in nature and offers a simple and expandable route to preparing derivatives of this valuable building block.

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    Cite this: J. Am. Chem. Soc. 2016, 138, 27, 8388–8391
    Click to copy citationCitation copied!
    https://doi.org/10.1021/jacs.6b04836
    Published June 29, 2016
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