17556-41-1Relevant articles and documents
Discovery of New Carbonyl Reductases Using Functional Metagenomics and Applications in Biocatalysis
Newgas, Sophie A.,Jeffries, Jack W. E.,Moody, Thomas S.,Ward, John M.,Hailes, Helen C.
, p. 3044 - 3052 (2021/04/26)
Enzyme discovery for use in the manufacture of chemicals, requiring high stereoselectivities, continues to be an important avenue of research. Here, a sequence directed metagenomics approach is described to identify short chain carbonyl reductases. PCR from a metagenomic template generated 37 enzymes, with an average 25% sequence identity, twelve of which showed interesting activities in initial screens. Six of the most productive enzymes were then tested against a panel of 21 substrates, including bulkier substrates that have been noted as challenging in biocatalytic reductions. Two enzymes were selected for further studies with the Wieland Miescher ketone. Notably, enzyme SDR-17, when co-expressed with a co-factor recycling system produced the anti-(4aR,5S) isomer in excellent isolated yields of 89% and 99% e.e. These results demonstrate the viability of a sequence directed metagenomics approach for the identification of multiple homologous sequences with low similarity, that can yield highly stereoselective enzymes with applicability in industrial biocatalysis. (Figure presented.).
Highly enantioselective construction of CF3-bearing all-carbon quaternary stereocenters: Hiral spiro-fused bisoxazoline ligands with 1,1′-binaphthyl sidearm for asymmetric Michael-type Friedel-Crafts reaction
Bao, Robert Li-Yuan,Fu, Kang,Shi, Lei
supporting information, (2021/11/27)
A novel class of chiral spiro-fused bisoxazoline ligands possessing a deep chiral pocket was prepared. The developed ligands have been employed in the nickel-catalyzed highly enantioselective Michael-type Friedel-Crafts reaction, affording the products bearing a trifluoromethylated all-carbon quaternary stereocenter with moderate to excellent yields (up to 99%) and good to excellent enantioselectivies (up to > 99.9% ee). Moreover, a proposed model of chiral pocket revealed that the attack of indole from the Re-face of β-CF3-β-disubstituted nitroalkene was favorable.
Synthesis of Unsymmetric Triarylmethanes Bearing CF 3-Substituted All-Carbon Quaternary Stereocenters: 1,6-Arylation of δ-Trifluo romethyl Substituted para -Quinone Methides
Ma, Yingang,Pang, Jingxiang,Pan, Xiaoguang,Ma, Shutao,Liu, Xigong,Liu, Lei
supporting information, p. 1619 - 1622 (2020/09/15)
Pre-synthesized δ-CF 3-δ-aryl-disubstituted para -quinone methides bearing δ-substituents were identified as isolable and storable substrates for 1,6-arylation reactions. A broad range of electron-rich arenes and heteroarenes participated in the arylation process, furnishing a wide array of unsymmetrical CF 3-substituted triarylmethanes in high efficiency. The mild and expeditious protocol exhibited broad scopes of both arene and para -quinone methide components.
