Nitroalkanes as Versatile Nucleophiles for Enzymatic
Synthesis of Noncanonical Amino Acids
Posted on 2019-08-23 - 17:45
C–C
bond-forming reactions often require nucleophilic carbon species rarely
compatible with aqueous reaction media, thus restricting their appearance
in biocatalysis. Here we report the use of nitroalkanes as a structurally
versatile class of nucleophilic substrates for C–C bond formation
catalyzed by variants of the β-subunit of tryptophan synthase
(TrpB). The enzymes accept a wide range of nitroalkanes to form noncanonical
amino acids, where the nitro group can serve as a handle for further
modification. Using nitroalkane nucleophiles greatly expands the scope
of compounds made by TrpB variants and establishes nitroalkanes as
a valuable substrate class for biocatalytic C–C bond formation.
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Romney, David K.; Sarai, Nicholas S.; Arnold, Frances H. (2019). Nitroalkanes as Versatile Nucleophiles for Enzymatic
Synthesis of Noncanonical Amino Acids. ACS Publications. Collection. https://doi.org/10.1021/acscatal.9b02089
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AUTHORS (3)
DR
David K. Romney
NS
Nicholas S. Sarai
FA
Frances H. Arnold