Highly Stereocontrolled One-Step Synthesis ofanti-β-Amino Alcohols from Organoboronic Acids, Amines, and α-Hydroxy Aldehydes

1998 ◽  
Vol 120 (45) ◽  
pp. 11798-11799 ◽  
Author(s):  
Nicos A. Petasis ◽  
Ilia A. Zavialov
Keyword(s):  
Amino Alcohols ◽  
Organoboronic Acids ◽  
One Step ◽  
Hydroxy Aldehydes

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.

scholarly journals A Novel One-Pot and One-Step Microwave-Assisted Cyclization-Methylation Reaction of Amino Alcohols and Acetylated Derivatives with Dimethyl Carbonate and TBAC

2014 ◽  
Vol 2014 ◽  
pp. 1-10 ◽  
Author(s):  
Adrián Ochoa-Terán ◽  
Leticia Guerrero ◽  
Ignacio A. Rivero
Keyword(s):  
Ionic Liquid ◽  
Dimethyl Carbonate ◽  
Amino Alcohols ◽  
Diethyl Carbonate ◽  
One Pot ◽  
Microwave Assisted ◽  
Methylation Reaction ◽  
One Step ◽  
Better Than

A simple and efficient microwave-assisted methodology for the synthesis of 4-substituted-3-methyl-1,3-oxazolidin-2-ones from amino alcohols catalyzed by a ionic liquid was developed. This novel one-pot and one-step cyclization-methylation reaction represents an easier and faster method than any other reported protocols that can be used to obtain the desired products in good yields and high purity. Applying microwave irradiation at 130°C in the presence of TBAC, dimethyl carbonate acts simultaneously as carbonylating and methylating agent and surprisingly promotes anin situbasic trans esterification when aN-acetylated amino alcohol is used as starting material. Furthermore, dimethyl carbonate worked better than diethyl carbonate in performing this reaction.

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