Combination of the Suzuki–Miyaura Cross‐Coupling Reaction with Engineered Transaminases

Dawood, Ayad W. H.; Bassut, Jonathan; Souza, Rodrigo O. M. A. de; Bornscheuer, Uwe T.

doi:10.1002/chem.201804366

Cited by 51 publications

(42 citation statements)

References 86 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…For example, the rationally engineered (S)-selective ATA from V. fluvialis catalyzed an ortho-biaryl ketone to the corresponding (S)-biaryl amine. 47 Bornscheuer and coworkers, 16 in parallel to us, 48…”

Section: Figure 1 Examples Of Biaryl-containing Drugs: Valsartane (1mentioning

confidence: 90%

Enantioselective One-Pot Synthesis of Biaryl-Substituted Amines by Combining Palladium and Enzyme Catalysis in Deep Eutectic Solvents

Paris

Telzerow

Ríos‐Lombardía

et al. 2019

ACS Sustainable Chem. Eng.

View full text Add to dashboard Cite

The first application of Deep Eutectic Solvents (DESs) in asymmetric bioamination of ketones has been accomplished. The amine transaminases (ATAs) turned out to be particularly stable in DES-buffer mixtures at a percentage of up to 75% (w/w) neoteric solvent. Moreover, this reaction medium was used to perform a chemoenzymatic cascade toward biaryl amines by coupling a Suzuki reaction sequentially with an enantioselective bioamination catalyzed by the recently discovered ATA from Exophiala xenobiotica (EX-TA). The solubilizing properties of DESs enabled the metal-catalyzed step at 200 mM loading of substrate and the subsequent biotransformation at 25 mM.

show abstract

Section: Figure 1 Examples Of Biaryl-containing Drugs: Valsartane (1mentioning

confidence: 90%

Enantioselective One-Pot Synthesis of Biaryl-Substituted Amines by Combining Palladium and Enzyme Catalysis in Deep Eutectic Solvents

Paris

Telzerow

Ríos‐Lombardía

et al. 2019

ACS Sustainable Chem. Eng.

View full text Add to dashboard Cite

show abstract

“…Uwe Bornscheuer's group demonstrated a Suzuki-Miyaura coupling in batch to produce a biaryl ketone substrate for a subsequent transaminase-catalyzed amination in flow (Scheme 6B). [143] Here, the ability of the transaminase reaction to tolerate 30% (v/v) DMF as well as salts and palladium from the first reaction step was key.…”

Section: Accepted Manuscriptmentioning

confidence: 99%

Looking Back: A Short History of the Discovery of Enzymes and How They Became Powerful Chemical Tools

Heckmann

Paradisi

2020

ChemCatChem

View full text Add to dashboard Cite

Enzymatic approaches to challenges in chemical synthesis are increasingly popular and very attractive to industry given their green nature and high efficiency compared to traditional methods. In this historical review we highlight the developments across several fields that were necessary to create the modern field of biocatalysis, with enzyme engineering and directed evolution at its core. We exemplify the modular, incremental, and highly unpredictable nature of scientific discovery, driven by curiosity, and showcase the resulting examples of cutting-edge enzymatic applications in industry.

show abstract

“…Accordingly, Bornscheuer et. al . reported such a sequential process in aqueous medium employing 4CHI‐TA [2 mM substrate concentration for the coupling step (DMF, 50 % v/v) and 1 mM for the bioamination (DMF, 30 % v/v)], several ( R )‐ meta ‐ and para ‐biaryl and pyridylphenyl amines being obtained with >99 % ee (Table , Entry 5).…”

Section: Chemoenzymatic Synthetic Cascadesmentioning

confidence: 99%

Non‐Conventional Media as Strategy to Overcome the Solvent Dilemma in Chemoenzymatic Tandem Catalysis

Kourist

González‐Sabín

2020

ChemCatChem

View full text Add to dashboard Cite

The amazing potential of multi‐catalytic cascade reactions to reduce the number of reaction steps and to solve synthetic problems brings the challenge of an increasing complexity that must be controlled. Particularly chemo‐enzymatic reactions are prone to conflicts regarding different optimal reaction conditions for chemical and biological catalysts. The preference of many chemical catalysts for hydrophobic (and often water‐free) solvent and of many enzymes for water poses a solvent dilemma. Recently, non‐conventional solvents have been very successful to provide suitable reaction media for catalysts that otherwise require very different solvents, and to alleviate fundamental problems such as the low solubility of many substrates in aqueous solvents. In the last few years, several examples underlined the considerable potential of ionic liquids and deep eutectic solvents for the engineering of cascade reactions. This mini‐review showcases the recent developments on the implementation of the so‐called non‐conventional media in such processes.

show abstract

Combination of the Suzuki–Miyaura Cross‐Coupling Reaction with Engineered Transaminases

Cited by 51 publications

References 86 publications

Enantioselective One-Pot Synthesis of Biaryl-Substituted Amines by Combining Palladium and Enzyme Catalysis in Deep Eutectic Solvents

Enantioselective One-Pot Synthesis of Biaryl-Substituted Amines by Combining Palladium and Enzyme Catalysis in Deep Eutectic Solvents

Looking Back: A Short History of the Discovery of Enzymes and How They Became Powerful Chemical Tools

Non‐Conventional Media as Strategy to Overcome the Solvent Dilemma in Chemoenzymatic Tandem Catalysis

Contact Info

Product

Resources

About