Chiral Amine Synthesis - Recent Developments and Trends for Enamide Reduction, Reductive Amination, and Imine Reduction

2010 ◽  
Vol 352 (5) ◽  
pp. 753-819 ◽  
Author(s):  
Thomas C. Nugent ◽  
Mohamed El-Shazly
Keyword(s):  
Reductive Amination ◽  
Chiral Amine ◽  
Recent Developments ◽  
Imine Reduction

scholarly journals Economy Assessment for the Chiral Amine Production with Comparison of Reductive Amination and Transamination Routes by Multi-Enzyme System

Catalysts ◽  
2020 ◽  
Vol 10 (12) ◽  
pp. 1451
Author(s):  
Heyu Huo ◽  
Guangxiao Yao ◽  
Shizhen Wang
Keyword(s):  
Reductive Amination ◽  
Nadh Oxidase ◽  
Glucose Dehydrogenase ◽  
Economic Assessment ◽  
Building Blocks ◽  
Unit Price ◽  
Chiral Amine ◽  
Process Comparison ◽  
Amine Dehydrogenase

Chiral amines are key building blocks for pharmaceuticals. Economic assessment of commercial potential of bioprocesses is needed for guiding research. Biosynthesis of (S)-α-methylbenzylamine (MBA) was selected as case study. For transamination route, transaminase coupled with glucose dehydrogenase and lactate dehydrogenase catalyzed the reaction with NADH (Nicotinamide adenine dinucleotide) regeneration. Amine dehydrogenase coupled with NADH oxidase, which catalyzed the reductive amination process. Comparison of biosynthesis cost by reductive amination and transamination routes was carried out. Economic assessment based on the framework of cost analysis and preliminary process information revealed that cost is greatly dependent on enzyme price. The results indicated that enhancing the activity of amine dehydrogenase by 4–5 folds can drop the unit price of reductive amination to $0.5–0.6/g, which make it competitive with transamination route.

Reductive Amination/Alkylation Reactions: The Recent Developments, Progresses, and Applications in Protein Chemical Biology Studies

2018 ◽  
Vol 15 (6) ◽  
pp. 755-761 ◽  
Author(s):  
Zhipeng A. Wang ◽  
Yan-Yu Liang ◽  
Ji-Shen Zheng
Keyword(s):  
Chemical Biology ◽  
Reductive Amination ◽  
High Efficiency ◽  
Protein Complexes ◽  
Protein Chemistry ◽  
Bioorthogonal Reactions ◽  
Chemistry Research ◽  
Amination Reaction ◽  
Recent Developments ◽  
Alkylation Reactions

The chemical modifications of proteins or protein complexes have been a challenging but fruitful task in the post-genomic era. Bioorthogonal reactions play an important role for the purpose of selective functionalization, localization, and labeling of proteins with natural or non-natural structures. Among these reactions, reductive amination stands out as one of the typical bioorthogonal reactions with high efficiency, good biocompatibility, and versatile applications. However, not many specific reviews exist to discuss the mechanism, kinetics, and their applications in a detailed manner. In this manuscript, we aim to summarize some current developments and mechanistic studies of reductive amination reaction and its applications. We hope reductive amination reaction can contribute to a wider scope of protein chemistry research en route in the chemical biology frontier as one of the well-known bioorthogonal reactions.

ChemInform Abstract: Biocatalytic Imine Reduction and Reductive Amination of Ketones

ChemInform ◽  
2015 ◽  
Vol 46 (30) ◽  
pp. no-no
Author(s):  
Joerg H. Schrittwieser ◽  
Stefan Velikogne ◽  
Wolfgang Kroutil
Keyword(s):  
Reductive Amination ◽  
Imine Reduction

scholarly journals Cover Picture: Biocatalytic Imine Reduction and Reductive Amination of Ketones (Adv. Synth. Catal. 8/2015)

2015 ◽  
Vol 357 (8) ◽  
pp. 1553-1553 ◽  
Author(s):  
Joerg H. Schrittwieser ◽  
Stefan Velikogne ◽  
Wolfgang Kroutil
Keyword(s):  
Reductive Amination ◽  
Imine Reduction

Imine Reduction and Reductive Amination

2007 ◽  
pp. 161-181
Author(s):  
Magnus Rueping ◽  
Erli Sugiono ◽  
Cengiz Azap ◽  
Thomas Theissmann ◽  
Andrey P. Antonchick ◽  
...  
Keyword(s):  
Reductive Amination ◽  
Imine Reduction

scholarly journals Characterization of imine reductases in reductive amination for the exploration of structure-activity relationships

2020 ◽  
Vol 6 (21) ◽  
pp. eaay9320 ◽  
Author(s):  
Sarah L. Montgomery ◽  
Ahir Pushpanath ◽  
Rachel S. Heath ◽  
James R. Marshall ◽  
Ulrike Klemstein ◽  
...  
Keyword(s):  
Asymmetric Synthesis ◽  
Reductive Amination ◽  
Chiral Amines ◽  
Sequence Motif ◽  
Sequence Structure ◽  
Reaction Conditions ◽  
Rational Engineering ◽  
Structure Activity ◽  
Imine Reduction

Imine reductases (IREDs) have shown great potential as catalysts for the asymmetric synthesis of industrially relevant chiral amines, but a limited understanding of sequence activity relationships makes rational engineering challenging. Here, we describe the characterization of 80 putative and 15 previously described IREDs across 10 different transformations and confirm that reductive amination catalysis is not limited to any particular subgroup or sequence motif. Furthermore, we have identified another dehydrogenase subgroup with chemoselectivity for imine reduction. Enantioselectivities were determined for the reduction of the model substrate 2-phenylpiperideine, and the effect of changing the reaction conditions was also studied for the reductive aminations of 1-indanone, acetophenone, and 4-methoxyphenylacetone. We have performed sequence-structure analysis to help explain clusters in activity across a phylogenetic tree and to inform rational engineering, which, in one case, has conferred a change in chemoselectivity that had not been previously observed.

scholarly journals Direct Asymmetric Reductive Amination for the Synthesis of (S)-Rivastigmine

Molecules ◽  
2018 ◽  
Vol 23 (9) ◽  
pp. 2207 ◽  
Author(s):  
Guorui Gao ◽  
Shaozhi Du ◽  
Yang Yang ◽  
Xue Lei ◽  
Haizhou Huang ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Reductive Amination ◽  
Asymmetric Total Synthesis ◽  
Ligand Complex ◽  
Chiral Amine ◽  
Ethyl Methyl

In this article we demonstrate how asymmetric total synthesis of (S)-rivastigmine has been achieved using direct asymmetric reductive amination as the key transformation in four steps. The route started with readily available and cheap m-hydroxyacetophenone, through esterification, asymmetric reductive amination, N-diphenylmethyl deprotection and reductive amination, to provide the final (S)-rivastigmine in 82% overall yield and 96% enantioselectivity. In the asymmetric reductive amination, catalysed by the iridium–phosphoramidite ligand complex and helped by some additives, the readily prepared 3-acetylphenyl ethyl(methyl)carbamate directly reductively coupled with diphenylmethanamine to yield the chiral amine product in 96% ee and 93% yield.

Biocatalytic Imine Reduction and Reductive Amination of Ketones

2015 ◽  
Vol 357 (8) ◽  
pp. 1655-1685 ◽  
Author(s):  
Joerg H. Schrittwieser ◽  
Stefan Velikogne ◽  
Wolfgang Kroutil
Keyword(s):  
Reductive Amination ◽  
Imine Reduction
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