Stereocontrolled catalytic asymmetric reduction of ketones with oxazaborolidines derived from new chiral amino alcohols

1993 ◽  
Vol 58 (17) ◽  
pp. 4511-4512 ◽  
Author(s):  
Yong Hae Kim ◽  
Doo Han Park ◽  
Il Suk Byun ◽  
I. K. Yoon ◽  
C. S. Park
Keyword(s):  
Asymmetric Reduction ◽  
Amino Alcohols ◽  
Catalytic Asymmetric ◽  
Reduction Of Ketones ◽  
Chiral Amino Alcohols

ChemInform Abstract: Asymmetric Reduction of Ketones with Sodium Aluminum Hydride Modified with Chiral Amino Alcohols.

ChemInform ◽  
2010 ◽  
Vol 33 (1) ◽  
pp. no-no
Author(s):  
M. G. Vinogradov ◽  
O. V. Mikhalev ◽  
V. A. Pavlov ◽  
V. A. Ferapontov ◽  
O. R. Malyshev ◽  
...  
Keyword(s):  
Asymmetric Reduction ◽  
Aluminum Hydride ◽  
Amino Alcohols ◽  
Sodium Aluminum Hydride ◽  
Reduction Of Ketones ◽  
Chiral Amino Alcohols

scholarly journals Biosynthesis of Chiral Amino Alcohols via an Engineered Amine Dehydrogenase in E. coli

2022 ◽  
Vol 9 ◽  
Author(s):  
Feifei Tong ◽  
Zongmin Qin ◽  
Hongyue Wang ◽  
Yingying Jiang ◽  
Junkuan Li ◽  
...  
Keyword(s):  
Reductive Amination ◽  
Asymmetric Reduction ◽  
Amino Alcohols ◽  
Saturation Mutagenesis ◽  
Preparative Scale ◽  
One Step ◽  
Amine Dehydrogenase ◽  
The One ◽  
Total Turnover ◽  
Chiral Amino Alcohols

Chiral amino alcohols are prevalent synthons in pharmaceuticals and synthetic bioactive compounds. The efficient synthesis of chiral amino alcohols using ammonia as the sole amino donor under mild conditions is highly desired and challenging in organic chemistry and biotechnology. Our previous work explored a panel of engineered amine dehydrogenases (AmDHs) derived from amino acid dehydrogenase (AADH), enabling the one-step synthesis of chiral amino alcohols via the asymmetric reductive amination of α-hydroxy ketones. Although the AmDH-directed asymmetric reduction is in a high stereoselective manner, the activity is yet fully excavated. Herein, an engineered AmDH derived from a leucine dehydrogenase from Sporosarcina psychrophila (SpAmDH) was recruited as the starting enzyme, and the combinatorial active-site saturation test/iterative saturation mutagenesis (CAST/ISM) strategy was applied to improve the activity. After three rounds of mutagenesis in an iterative fashion, the best variant wh84 was obtained and proved to be effective in the asymmetric reductive amination of 1-hydroxy-2-butanone with 4-fold improvements in kcat/Km and total turnover number (TTN) values compared to those of the starting enzyme, while maintaining high enantioselectivity (ee >99%) and thermostability (T5015 >53°C). In preparative-scale reaction, the conversion of 100 and 200 mM 1-hydroxy-2-butanone catalyzed by wh84 was up to 91–99%. Insights into the source of an enhanced activity were gained by the computational analysis. Our work expands the catalytic repertoire and toolbox of AmDHs.

Penicillamine as a ligand in the catalytic asymmetric reduction of ketones

2002 ◽  
Vol 80 (8) ◽  
pp. 885-888 ◽  
Author(s):  
Stephen Hanessian ◽  
Eric Jnoff ◽  
Andrew M Griffin
Keyword(s):  
Amino Acids ◽  
Amino Acid ◽  
Asymmetric Reduction ◽  
Catalytic Asymmetric ◽  
Reduction Of Ketones

Amino acids derived from D-penicillamine and thiazolidines were studied as ligands for the catalytic asymmetric reduction of ketones with borane. Enantioselectivities up to 83% ee were observed.Key words: asymmetric reduction, penicillamine, thiazolidine, amino acid.

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