929260-29-7Relevant articles and documents
Ketoreductase catalyzed stereoselective bioreduction of α-nitro ketones
Wang, Zexu,Wu, Xiaofan,Li, Zhining,Huang, Zedu,Chen, Fener
supporting information, p. 3575 - 3580 (2019/04/14)
We report here the stereoselective bioreduction of α-nitro ketones catalyzed by ketoreductases (KREDs) with publicly known sequences. YGL039w and RasADH/SyADH were able to reduce 23 class I substrates (1-aryl-2-nitro-1-ethanone (1)) and ten class II substrates (1-aryloxy-3-nitro-2-propanone (4)) to furnish both enantiomers of the corresponding β-nitro alcohols, with good-to-excellent conversions (up to >99%) and enantioselectivities (up to >99% ee) being achieved in most cases. To the best of our knowledge, KRED-mediated reduction of class II α-nitro ketones (1-aryloxy-3-nitro-2-propanone (4)) is unprecedented. Select β-nitro alcohols, including the synthetic intermediates of bioactive molecules (R)-tembamide, (S)-tembamide, (S)-moprolol, (S)-toliprolol and (S)-propanolol, were stereoselectively synthesized in preparative scale with 42% to 90% isolated yields, showcasing the practical potential of our developed system in organic synthesis. Finally, the advantage of using KREDs with known sequence was demonstrated by whole-cell catalysis, in which β-nitro alcohol (R)-2k, the key synthetic intermediate of hypoglycemic natural product (R)-tembamide, was produced in a space-time yield of 178 g L?1 d?1 as well as 95% ee by employing the whole cells of a recombinant E. coli strain coexpressing RasADH and glucose dehydrogenase as the biocatalyst.
The synthesis of chiral tridentate ligands from L-proline and their application in the copper(II)-catalyzed enantioselective Henry reaction
Xu, Daqian,Sun, Qiangsheng,Quan, Zhengjun,Sun, Wei,Wang, Xicun
, p. 954 - 963 (2017/07/11)
A series of chiral tridentate ligands derived from readily available enantiopure L-proline were designed and synthesized. The ligands together with Cu(OAc)2 were successfully used in asymmetric Henry reactions. Various structurally divergent aldehydes and nitromethane were converted into versatile β-nitro alcohols in MeOH at room temperature with very good yields (up to 85%) and enantioselectivities (up to 86%).
Mining catalytic promiscuity from: Thermophilic archaea: An acyl-peptide releasing enzyme from Sulfolobus tokodaii (ST0779) for nitroaldol reactions
Yu, Xiaoxiao,Pérez, Bianca,Zhang, Zhefei,Gao, Renjun,Guo, Zheng
, p. 2753 - 2761 (2016/05/24)
This work demonstrates that the thermophiles can be a rich source to mine catalytic promiscuity, whereby an acyl-peptide releasing enzyme from Sulfolobus tokodaii (ST0779) is identified to be a promising biocatalyst to mediate the Henry (nitroaldol) react
