Reductive Amination of Keto Acids

Hummel, Werner; Gröger, Harald

doi:10.1002/9783527639861.ch28

Cited by 9 publications

(1 citation statement)

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“…While there are many enzymes which can carry out reductive amination using ammonia, few examples are known to employ alkyl amines (Hummel and Groger, 2012;Schrittwieser et al, 2015;. Classes of enzymes that are now known to perform this transformation include opine dehydrogenases (ODHs), N-methyl amino acid dehydrogenases (NMAADHs), ketimine reductases (KIREDs), pyrroline-5-carboxylate reductases (P5CRs) and imine reductases (IREDs), each of which is discussed below.…”

Section: Dehydrogenasesmentioning

confidence: 99%

N-Alkyl-α-amino acids in Nature and their biocatalytic preparation

Hyslop

Lovelock

Watson

et al. 2019

Journal of Biotechnology

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The N-alkyl amino acid moiety is widespread in Nature.  A number of commercial products related to health contain the N-alkylated amino acid moiety.  Biocatalysis can provide more efficient and sustainable methods of accessing the N-alkyl amino acid moiety than traditional methods.  Several new enzyme classes comprising N-methyl transferases and dehydrogenases can be used for the synthesis of N-alkyl amino acids.

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Section: Dehydrogenasesmentioning

confidence: 99%

N-Alkyl-α-amino acids in Nature and their biocatalytic preparation

Hyslop

Lovelock

Watson

et al. 2019

Journal of Biotechnology

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Asymmetric Synthesis with Recombinant Whole‐Cell Catalysts

2016

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c h a p t e r 2 3 INTRODUCTIONAsymmetric catalytic transformations play a central role in the field of organic chemistry and are of great interest for applications in the chemical and pharmaceutical industry. Among those, hydrolytic and reverse reactions to form carboxylate deriva tives as well as C─C bond-forming and redox reactions are of particular importance. For a long time this field was dominated by the use of chemocatalysts [1]. For example, numerous chiral heavy-metal complexes have been found to be highly efficient cat alysts, on a technical scale, in particular, for the asymmetric reduction of imines, ketones, and enamides. A representative success story is imine reduction for the man ufacture of metolachlor as one of the largest industrially applied asymmetric chemo catalytic processes to date, and the widely technically applied hydrogenation technology for the reduction of ketones and enamides, for which Noyori and Knowles were awarded the Nobel Prize [2]. An alternative for the production of chiral building blocks, with a continuously increasing number of examples, also on an industrial scale, is biocatalysis. Known for a long time, the use of biocatalytic alternatives has also been limited for a long time, which has been due to-among others-the following two reasons: (i) wild-type whole cells such as baker's yeast require a large amount of biomass (due to the forma tion of the desired enzymes in the cell only in low amounts) and often give unsatisfy ing enantioselectivities (due to the action of more than one enzyme), and (ii) the use of isolated enzymes requires additional costs for cell disruption and enzyme isolation as well as the addition of an external amount of cofactor. Due to impressive progress in the field of molecular biology, these limitations have often been overcome. High overexpression of the desired enzyme in recombinant host organism and high cell density fermentation technology provide efficient and economically attractive access to these microorganisms (so-called designer cells), which contain exclusively the desired biocatalyst (enzyme) in large amounts. Such designer cells can be used directly in organic synthetic reactions without the need to isolate the enzyme in additional downstream operation steps. The presence of the cofactor in the cells requires no addition of an external amount of cofactors or supply thereof in very low amount only. Due to these advantages, recombinant whole cells overexpressing cofactor dependent enzymes have become very attractive catalysts for asymmetric synthesis. This is underlined by an increasing number of recent organic biotransformations based on the use of such "designer cells."

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Merging MOF Chemistry & Biocatalysis: A Perspective for Achieving Efficient Organic Synthetic Processes and Applications in the Chemical Industry?

Gröger,

Allahverdiyev,

Yang

et al. 2024

Adv Funct Materials

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Biocatalysis has emerged in recent decades toward a widely applied catalysis technology in the chemical industry. In particular the fine chemicals and pharmaceuticals industries benefit from the advantages of biocatalysis, which made its way to a dominating industrial core technology for manufacturing chiral molecules. However, often biocatalysis is still to a certain extent away from having solved all challenges being needed for a “perfect industrial process technology”. Among existing challenges are, e.g., stability under process conditions and easy separation of the catalyst from the reaction mixture with the additional option of recyclability. Here metal‐organic framework (MOF) structures offer unique advantages, which can be beneficial for biocatalysis. A particular valuable option is integration of enzymes into MOF‐subunits, thus having a potential positive impact on stability (by reducing the tendency of unfolding) and enabling compartmentalization as a beneficial strategy in, e.g., chemoenzymatic synthesis. In this “Perspective”‐article, first the state of the art in biocatalysis is briefly summarized together with current challenges. Then, a short overview about current research achievements in “merging” MOF chemistry and biocatalysis is given as well as an outlook written from a biocatalysis practitioner's view, how MOF‐enzyme hybrid systems can play a major role in future process development to overcome existing hurdles of enzymatic catalysis.

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Reductive Amination of Keto Acids

Cited by 9 publications

References 113 publications

N-Alkyl-α-amino acids in Nature and their biocatalytic preparation

N-Alkyl-α-amino acids in Nature and their biocatalytic preparation

Asymmetric Synthesis with Recombinant Whole‐Cell Catalysts

Merging MOF Chemistry & Biocatalysis: A Perspective for Achieving Efficient Organic Synthetic Processes and Applications in the Chemical Industry?

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