Reductive Amination of Biobased Levulinic Acid to Unnatural Chiral γ-Amino Acid Using an Engineered Amine Dehydrogenase

2020 ◽  
Vol 8 (46) ◽  
pp. 17054-17061
Author(s):  
Rui-Feng Cai ◽  
Lei Liu ◽  
Fei-Fei Chen ◽  
Aitao Li ◽  
Jian-He Xu ◽  
...  
Keyword(s):  
Amino Acid ◽  
Levulinic Acid ◽  
Reductive Amination ◽  
Amine Dehydrogenase

scholarly journals Selectively Reductive Amination of Levulinic Acid with Aryl amines to N-substituted Aryl Pyrroles

2021 ◽  
Author(s):  
Cailing Wu ◽  
Mengjie Lou ◽  
Mingming Sun ◽  
Huiyong Wang ◽  
Zhiyong Li ◽  
...  
Keyword(s):  
Levulinic Acid ◽  
Reductive Amination ◽  
Aryl Amines

Insights into Cascade and Sequential one pot pathways for reductive amination of aldehydes paired with bio-derived levulinic acid to N-substituted pyrrolidones using molecular hydrogen

2022 ◽  
Author(s):  
Tejas A Gokhale ◽  
Amol Bhanudas Raut ◽  
Sheetal K Chawla ◽  
Bhalchandra Mahadeo Bhanage
Keyword(s):  
Molecular Hydrogen ◽  
Levulinic Acid ◽  
Reductive Amination ◽  
One Pot ◽  
Aryl Aldehydes

This work aims to explore cascade and sequential one pot syntheses pathways for N-substituted pyrrolidones from aryl aldehydes and bio-derived levulinic acid (LA) using molecular hydrogen and ammonia. This process...

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.

scholarly journals 2,3-Diaminopropanols Obtained from d-Serine as Intermediates in the Synthesis of Protected 2,3-l-Diaminopropanoic Acid (l-Dap) Methyl Esters

Molecules ◽  
2020 ◽  
Vol 25 (6) ◽  
pp. 1313
Author(s):  
Andrea Temperini ◽  
Donatella Aiello ◽  
Fabio Mazzotti ◽  
Constantinos M. Athanassopoulos ◽  
Pierantonio De Luca ◽  
...  
Keyword(s):  
Amino Acid ◽  
Reductive Amination ◽  
Methyl Esters ◽  
Primary Amines ◽  
Synthetic Approach ◽  
Protecting Group ◽  
Synthetic Strategy ◽  
Crude Product ◽  
Diaminopropanoic Acid ◽  
Acid Labile

A synthetic strategy for the preparation of two orthogonally protected methyl esters of the non-proteinogenic amino acid 2,3-l-diaminopropanoic acid (l-Dap) was developed. In these structures, the base-labile protecting group 9-fluorenylmethyloxycarbonyl (Fmoc) was paired to the p-toluensulfonyl (tosyl, Ts) or acid-labile tert-butyloxycarbonyl (Boc) moieties. The synthetic approach to protected l-Dap methyl esters uses appropriately masked 2,3-diaminopropanols, which are obtained via reductive amination of an aldehyde prepared from the commercial amino acid Nα-Fmoc-O-tert-butyl-d-serine, used as the starting material. Reductive amination is carried out with primary amines and sulfonamides, and the process is assisted by the Lewis acid Ti(OiPr)4. The required carboxyl group is installed by oxidizing the alcoholic function of 2,3-diaminopropanols bearing the tosyl or benzyl protecting group on the 3-NH2 site. The procedure can easily be applied using the crude product obtained after each step, minimizing the need for chromatographic purifications. Chirality of the carbon atom of the starting d-serine template is preserved throughout all synthetic steps.

A new retro-aza-ene reaction: formal reductive amination of an α-keto acid to an α-amino acid

Tetrahedron ◽  
1992 ◽  
Vol 48 (9) ◽  
pp. 1715-1728 ◽  
Author(s):  
David B. Berkowitz ◽  
W. Bernd Schweizer
Keyword(s):  
Amino Acid ◽  
Reductive Amination ◽  
Keto Acid ◽  
Ene Reaction

Reductive amination of levulinic acid to N-substituted pyrrolidones over RuCl3 metal ion anchored in ionic liquid immobilized on graphene oxide

2020 ◽  
Vol 383 ◽  
pp. 206-214 ◽  
Author(s):  
Amol B. Raut ◽  
Vaishali S. Shende ◽  
Takehiko Sasaki ◽  
Bhalchandra M. Bhanage
Keyword(s):  
Ionic Liquid ◽  
Graphene Oxide ◽  
Metal Ion ◽  
Levulinic Acid ◽  
Reductive Amination

Facile Formation of Novel Carbohydrate-Amino Acid Conjugates by Reductive Amination.

ChemInform ◽  
2003 ◽  
Vol 34 (41) ◽  
Author(s):  
Saskia Weingarten ◽  
Joachim Thiem
Keyword(s):  
Amino Acid ◽  
Reductive Amination ◽  
Amino Acid Conjugates
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