cs9b02089_si_001.pdf (691.13 kB)
Nitroalkanes as Versatile Nucleophiles for Enzymatic Synthesis of Noncanonical Amino Acids
journal contribution
posted on 2019-08-23, 17:45 authored by David K. Romney, Nicholas S. Sarai, Frances H. ArnoldC–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.