Romney David K, Sarai Nicholas S, Arnold Frances H
Division of Chemistry and Chemical Engineering 210-41, California Institute of Technology, 1200 East California Boulevard, Pasadena, California 91125, United States.
ACS Catal. 2019 Sep 6;9(9):8726-8730. doi: 10.1021/acscatal.9b02089. Epub 2019 Aug 20.
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, here 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.
碳-碳键形成反应通常需要亲核碳物种，而这些物种很少能与水性反应介质兼容，因此限制了它们在生物催化中的应用。在此，我们报道了使用硝基烷烃作为一类结构多样的亲核底物，用于色氨酸合酶（TrpB）β亚基变体催化的碳-碳键形成反应。这些酶能接受多种硝基烷烃以形成非天然氨基酸，在此，硝基可作为进一步修饰的基团。使用硝基烷烃亲核试剂极大地扩展了TrpB变体所制备化合物的范围，并确立了硝基烷烃作为生物催化碳-碳键形成的一种有价值的底物类别。
