Engineered Biocatalysts for Enantioselective Reductive Aminations of Cyclic Secondary Amines

Burke, Ashleigh J.; Lister, Thomas M.; Marshall, Judi; Brown, Murray J. B.; Lloyd, Richard C.; Green, Anthony P.; Turner, Nicholas J.

doi:10.1002/cctc.202300256

Cited by 3 publications

(2 citation statements)

References 38 publications

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“…These biotransformations yield crucial motifs present in active pharmaceutical ingredients (Clopidrogel, Efinaconazole, Donepezil) and other bioactive molecules (Scheme 25b). 95 In 2023, Husain's group reported a general-purpose biocatalytic method that uses the IRED to synthesize a variety of substituted tetrahydrobenzoazole diazepines. The IREDs, mainly derived from Streptomyces GF3587, Katambe, and Cysticillus ferobacillus, have high catalytic activity against heptamembered cyclic imines with high enantiomeric excess (up to >99%) and isolation yield (up to 96%).…”

Section: Synthesis Of Importantmentioning

confidence: 99%

“…The mutant Redam-361-L80S exhibited robust catalytic activity against challenging cyclic amines, such as piperidine and morpholine derivatives. These biotransformations yield crucial motifs present in active pharmaceutical ingredients (Clopidrogel, Efinaconazole, Donepezil) and other bioactive molecules (Scheme b) …”

Section: Imine-reductase-mediated Synthesis Of Important Chiral Amine...mentioning

confidence: 99%

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Application of Imine Reductase in Bioactive Chiral Amine Synthesis

Wang,

Gao,

Gao

et al. 2024

Org. Process Res. Dev.

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Nitrogen-containing compounds, especially those with chiral amine structures, play a pivotal role in the field of organic active pharmaceutical ingredients. Traditional racemate resolution and chemical synthesis methods for the preparation of chiral amines suffer drawbacks such as high cost and environmental pollution. Over the past decades, stereoselective synthesis of nitrogen-containing compounds by biocatalytic methods such as imine reductase (IRED)-mediated transformation has become increasingly prominent. The prominence of imine reductases lies in their capacity to catalyze the reductive amination of aldehydes or ketones with primary or secondary amines, as well as their broader substrate scope. Furthermore, imine reductases exhibit diverse catalytic cycling systems that are unaffected by adverse reaction equilibria. This article focuses on the development of drug molecules or intermediates in biocatalytic synthesis mediated by imine reductase.

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Section: Synthesis Of Importantmentioning

confidence: 99%

Section: Imine-reductase-mediated Synthesis Of Important Chiral Amine...mentioning

confidence: 99%

Application of Imine Reductase in Bioactive Chiral Amine Synthesis

Wang,

Gao,

Gao

et al. 2024

Org. Process Res. Dev.

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Recent advances in biocatalytic C–N bond-forming reactions

Yin,

Wang,

Liu

2024

Bioorganic Chemistry

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Salient Achievements in Synthetic Organic Chemistry Enabled by Mechanochemical Activation

Juaristi

Avila‐Ortiz

2023

Synthesis

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Although known for millenia, it is only recently that mechanochemistry has caught serious attention by many chemists. Indeed, during the past 15 years an extraordinary number of reports concerning solid-state chemical transformations through grinding and milling techniques has been recorded. This short review discusses the circumstances that led to such renaissance, highlighting the present intense interest in so-called green chemistry, the enabling capacity of mechanochemistry to handle insoluble substrates, and the finding of the profound influence that additives can have on mechanochemically activated reactions. The core of this account focuses on salient developments in synthetic organic chemistry, especially in amino acid and peptide mechanosynthesis, the successful employment of mechanochemical activation in combination with asymmetric organocatalysis, the promising combination of mechanochemical activation with enzymatic and whole cell biocatalysis, and the remarkable achievement of multicomponent selective reactions via complex, multistep reaction pathways. The final section is dedicated to comment on some pending tasks in the area, such as scaling-up of milling processes to be of practical use in the chemical industry, the requirement of easier and more efficient control of reaction parameters and monitoring devices, and consequently the careful analysis of additional procedures for a proper understanding of mechanochemical phenomena.

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Engineered Biocatalysts for Enantioselective Reductive Aminations of Cyclic Secondary Amines

Cited by 3 publications

References 38 publications

Application of Imine Reductase in Bioactive Chiral Amine Synthesis

Application of Imine Reductase in Bioactive Chiral Amine Synthesis

Recent advances in biocatalytic C–N bond-forming reactions

Salient Achievements in Synthetic Organic Chemistry Enabled by Mechanochemical Activation

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