Engineering the large pocket of an (S)-selective transaminase for asymmetric synthesis of (S)-1-amino-1-phenylpropane

2021 ◽  
Author(s):  
Youyu Xie ◽  
Feng Xu ◽  
Lin Yang ◽  
He Liu ◽  
Xiangyang Xu ◽  
...  
Keyword(s):  
Asymmetric Synthesis ◽  
Environmentally Benign ◽  
Chiral Amine ◽  
Synthesis Route

Amine transaminases offer an environmentally benign chiral amine asymmetric synthesis route.

Asymmetric Synthesis of α-Chloro-α-halo Ketones by Decarboxylative Chlorination of α-Halo-β-ketocarboxylic Acids

Synthesis ◽  
2019 ◽  
Vol 51 (23) ◽  
pp. 4385-4392 ◽  
Author(s):  
Kazumasa Kitahara ◽  
Haruna Mizutani ◽  
Seiji Iwasa ◽  
Kazutaka Shibatomi
Keyword(s):  
Asymmetric Synthesis ◽  
Chiral Amine

Chiral α-chloro-α-fluoro ketones were synthesized by enantio­selective decarboxylative chlorination of α-chloro-β-ketocarboxylic acids in the presence of a chiral amine catalyst. The reaction yielded the corresponding α-chloro-α-fluoro ketones with moderate-to-high enantioselectivity (up to 90% ee). The method was also applied to the synthesis of α-bromo-α-chloro ketones with 90% ee.

Asymmetric synthesis of trans-2,5-diphenylpyrrolidine: A C2-symmetric chiral amine

1995 ◽  
Vol 6 (2) ◽  
pp. 409-418 ◽  
Author(s):  
J Michael Chong ◽  
Ian S Clarke ◽  
Iris Koch ◽  
Peter C Olbach ◽  
Nicholas J Taylor
Keyword(s):  
Asymmetric Synthesis ◽  
Chiral Amine

Asymmetric synthesis of chiral amine in organic solvent and in-situ product recovery for process intensification: A case study

2017 ◽  
Vol 117 ◽  
pp. 97-104 ◽  
Author(s):  
Yamini Satyawali ◽  
Ehiaze Ehimen ◽  
Lieve Cauwenberghs ◽  
Miranda Maesen ◽  
Pieter Vandezande ◽  
...  
Keyword(s):  
Organic Solvent ◽  
Asymmetric Synthesis ◽  
Process Intensification ◽  
Product Recovery ◽  
Chiral Amine ◽  
In Situ Product Recovery

scholarly journals Conversion of racemic alcohols to optically pure amine precursors enabled by catalyst dynamic kinetic resolution: experiment and computation

2020 ◽  
Vol 56 (64) ◽  
pp. 9094-9097
Author(s):  
Luis Miguel Azofra ◽  
Mai Anh Tran ◽  
Viktoriia Zubar ◽  
Luigi Cavallo ◽  
Magnus Rueping ◽  
...  
Keyword(s):  
Asymmetric Synthesis ◽  
Base Metal ◽  
Kinetic Resolution ◽  
Dynamic Kinetic Resolution ◽  
Chiral Amine ◽  
Optically Pure

An unprecedented base metal catalysed asymmetric synthesis of α-chiral amine precursors from racemic alcohols is reported.

Asymmetric synthesis of 3-substituted-2-exo-methylenecyclohexanones via 1,5-diastereoselection by using a chiral amine

1990 ◽  
Vol 55 (2) ◽  
pp. 408-410 ◽  
Author(s):  
Rui Tamura ◽  
Kenichiro Watabe ◽  
Hitoshi Katayama ◽  
Hitomi Suzuki ◽  
Yukio Yamamoto
Keyword(s):  
Asymmetric Synthesis ◽  
Chiral Amine

scholarly journals Engineering of Reductive Aminases for Asymmetric Synthesis of Enantiopure Rasagiline

2021 ◽  
Vol 9 ◽  
Author(s):  
Kai Zhang ◽  
Yuanzhi He ◽  
Jiawei Zhu ◽  
Qi Zhang ◽  
Luyao Tang ◽  
...  
Keyword(s):  
Transition Metal ◽  
Chemical Synthesis ◽  
Asymmetric Synthesis ◽  
Rational Design ◽  
Enantiomeric Excess ◽  
Industrial Applications ◽  
Viable Alternative ◽  
Environmentally Benign ◽  
Secondary Amines ◽  
Metal Catalyzed

Reductive aminases (RedAms) for the stereoselective amination of ketones represent an environmentally benign and economically viable alternative to transition metal–catalyzed asymmetric chemical synthesis. Here, we report two RedAms from Aspergillus calidoustus (AcRedAm) and bacteria (BaRedAm) with NADPH-dependent features. The enzymes can synthesize a set of secondary amines using a broad range of ketone and amine substrates with up to 97% conversion. To synthesize the pharmaceutical ingredient (R)-rasagiline, we engineered AcRedAm through rational design to obtain highly stereoselective mutants. The best mutant Q237A from AcRedAm could synthesize (R)-rasagiline with >99% enantiomeric excess with moderate conversion. The features of AcRedAm and BaRedAm highlight their potential for further study and expand the biocatalytic toolbox for industrial applications.

ChemInform Abstract: Asymmetric Synthesis of 3-Substituted 2-exo-Methylenecyclohexanones via 1,5-Diastereoselection by Using a Chiral Amine.

ChemInform ◽  
1990 ◽  
Vol 21 (24) ◽  
Author(s):  
R. TAMURA ◽  
K. WATABE ◽  
H. KATAYAMA ◽  
H. SUZUKI ◽  
Y. YAMAMOTO
Keyword(s):  
Asymmetric Synthesis ◽  
Chiral Amine
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