1574-87-4Relevant articles and documents
Stereodivergent Evolution of Artificial Enzymes for the Michael Reaction
Garrabou, Xavier,Macdonald, Duncan Stuart,Wicky, Basile I. M.,Hilvert, Donald
supporting information, p. 5288 - 5291 (2018/04/06)
Enzymes are valuable biocatalysts for asymmetric synthesis due to their exacting stereocontrol. Changing the selectivity of an existing catalyst for new applications is, however, challenging. Here we show that, in contrast, the stereoselectivity of an art
Enantiocomplementary synthesis of γ-nitroketones using designed and evolved carboligases
Garrabou, Xavier,Verez, Rebecca,Hilvert, Donald
supporting information, p. 103 - 106 (2017/05/16)
Artificial enzymes created by computational design and directed evolution are versatile biocatalysts whose promiscuous activities represent potentially attractive starting points for divergent evolution in the laboratory. The artificial aldolase RA9S.5-8, for example, exploits amine catalysis to promote mechanistically diverse carboligations. Here we report that RA95.5-8 variants catalyze the asymmetric synthesis of γ-nitroketones via two alternative enantiocomplementary Michael-type reactions: enamine-mediated addition of acetone to nitrostyrenes, and nitroalkane addition to conjugated ketones activated as iminium ions. In addition, a cascade of three aldolasecatalyzed reactions enables one-pot assembly of γ-nitroketones from three simpler building blocks. Together, our results highlight the chemical versatility of artificial aldolases for the practical synthesis of important chiral synthons.
Continuous asymmetric Michael addition of ketones to β-nitroolefins(1R,2R)-(+)-1,2-DPEN-modified sulfonic acid resin
Tian, Jun,Zhang, Chao,Qi, Xuefei,Yan, Xilong,Li, Yang,Chen, Ligong
, p. 724 - 728 (2015/02/19)
A trifunctional catalyst was successfully prepared by bonding (1R,2R)-(+)-1,2-DPEN to sulfonic acid resin. The catalyst was characterized by elemental analysis, thermogravimetric (TG) analysis and infrared (IR) spectroscopy. The results indicated the coex