Asymmetric Reduction of Aryl Ketones by Whole Cells of Pichia etchellsii AS2.625 Using β-Cyclodextrin as an Additive

2016 ◽  
Vol 13 (9) ◽  
pp. 5638-5644
Author(s):  
Jing-Wen Yang ◽  
Chen Chen ◽  
Jian-Bo Chen ◽  
Yi Xu
Keyword(s):  
Asymmetric Reduction ◽  
Whole Cells ◽  
Pichia Etchellsii ◽  
Aryl Ketones

Highly Productive CNN Pincer Ruthenium Catalysts for the Asymmetric Reduction of Alkyl Aryl Ketones

2009 ◽  
Vol 15 (3) ◽  
pp. 726-732 ◽  
Author(s):  
Walter Baratta ◽  
Giorgio Chelucci ◽  
Santo Magnolia ◽  
Katia Siega ◽  
Pierluigi Rigo
Keyword(s):  
Asymmetric Reduction ◽  
Ruthenium Catalysts ◽  
Alkyl Aryl ◽  
Aryl Ketones

Asymmetric reduction of alkyl aryl ketones in the binding domain of bovine serum albumin

1981 ◽  
Vol 10 (1) ◽  
pp. 104-113 ◽  
Author(s):  
Toyonari Sugimoto ◽  
Toshio Kokubo ◽  
Yasuo Matsumura ◽  
Jinsei Miyazaki ◽  
Shigeo Tanimoto ◽  
...  
Keyword(s):  
Bovine Serum Albumin ◽  
Serum Albumin ◽  
Bovine Serum ◽  
Asymmetric Reduction ◽  
Binding Domain ◽  
Alkyl Aryl ◽  
Aryl Ketones

scholarly journals Characterization of a Carbonyl Reductase from Rhodococcus erythropolis WZ010 and Its Variant Y54F for Asymmetric Synthesis of (S)-N-Boc-3-Hydroxypiperidine

Molecules ◽  
2018 ◽  
Vol 23 (12) ◽  
pp. 3117 ◽  
Author(s):  
Xiangxian Ying ◽  
Jie Zhang ◽  
Can Wang ◽  
Meijuan Huang ◽  
Yuting Ji ◽  
...  
Keyword(s):  
Asymmetric Reduction ◽  
Rhodococcus Erythropolis ◽  
Catalytic Efficiency ◽  
Carbonyl Reductase ◽  
Specific Enzyme ◽  
Practical Applications ◽  
Whole Cells ◽  
E Coli ◽  
Irreversible Reduction

The recombinant carbonyl reductase from Rhodococcus erythropolis WZ010 (ReCR) demonstrated strict (S)-stereoselectivity and catalyzed the irreversible reduction of N-Boc-3-piperidone (NBPO) to (S)-N-Boc-3-hydroxypiperidine [(S)-NBHP], a key chiral intermediate in the synthesis of ibrutinib. The NAD(H)-specific enzyme was active within broad ranges of pH and temperature and had remarkable activity in the presence of higher concentration of organic solvents. The amino acid residue at position 54 was critical for the activity and the substitution of Tyr54 to Phe significantly enhanced the catalytic efficiency of ReCR. The kcat/Km values of ReCR Y54F for NBPO, (R/S)-2-octanol, and 2-propanol were 49.17 s−1 mM−1, 56.56 s−1 mM−1, and 20.69 s−1 mM−1, respectively. In addition, the (S)-NBHP yield was as high as 95.92% when whole cells of E. coli overexpressing ReCR variant Y54F catalyzed the asymmetric reduction of 1.5 M NBPO for 12 h in the aqueous/(R/S)-2-octanol biphasic system, demonstrating the great potential of ReCR variant Y54F for practical applications.

Syntheses of 1,2-Amino Alcohols and Their Applications for Oxazaborolidine Catalyzed Enantioselective Reduction of Aromatic Ketones

2007 ◽  
Vol 60 (3) ◽  
pp. 196 ◽  
Author(s):  
Namdev S. Vatmurge ◽  
Braja G. Hazra ◽  
Vandana S. Pore
Keyword(s):  
Amino Alcohol ◽  
Good Yield ◽  
Asymmetric Reduction ◽  
Enantiomeric Excess ◽  
Amino Alcohols ◽  
Secondary Alcohols ◽  
Aromatic Ketones ◽  
Enantioselective Reduction ◽  
Aryl Ketones

Six new chiral 1,2-amino alcohol derivatives have been synthesized starting from (1R,2R)-2-amino-1-phenylpropane-1,3-diol. Asymmetric reduction of aryl ketones with in-situ generated oxazaborolidine from these amino alcohol derivatives and BH3·Me2S afforded secondary alcohols with good yield and moderate to high enantiomeric excess.

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