《Asymmetric Alkylation of Ketones Catalyzed by Engineered TrpB》 was written by Watkins-Dulaney, Ella J.; Dunham, Noah P.; Straathof, Sabine; Turi, Soma; Arnold, Frances H.; Buller, Andrew R.. Electric Literature of C9H7NOThis research focused onTrpB ketone alkylation catalysis propiophenone; asymmetric catalysis; biocatalysis; directed evolution; ketones; nitrogen heterocycles. The article conveys some information:
The β-subunit of tryptophan synthase (TrpB) catalyzes a PLP-mediated β-substitution reaction between indole and serine to form -Trp. A succession of TrpB protein engineering campaigns to expand the enzyme′s nucleophile substrate range has enabled the biocatalytic production of diverse non-canonical amino acids (ncAAs). Here, we show that ketone-derived enolates can serve as nucleophiles in the TrpB reaction to achieve the asym. alkylation of ketones, an outstanding challenge in synthetic chem. We engineered TrpB by directed evolution to catalyze the asym. alkylation of propiophenone and 2-fluoroacetophenone with a high degree of selectivity. In reactions with propiophenone, preference for the opposite product diastereomer emerges over the course of evolution, demonstrating that full control over the stereochem. at the new chiral center can be achieved. The addition of this new reaction to the TrpB platform is a crucial first step toward the development of efficient methods to synthesize non-canonical prolines and other chirally dense nitrogen heterocycles. In the part of experimental materials, we found many familiar compounds, such as 3-Oxo-3-phenylpropanenitrile(cas: 614-16-4Electric Literature of C9H7NO)
3-Oxo-3-phenylpropanenitrile(cas: 614-16-4) has been used in the synthesis of substituted naphtho[1,8-bc]pyrans. It was also used as building block in the preparation of 4H-pyrans, 2-pyridones, furans and carbocyclics.Electric Literature of C9H7NO
Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts