Biocatalytic Phosphorylation of Metabolites

Gauss, Dominik; Schönenberger, Bernhard; Molla, Getachew Shibabaw; Kinfu, Birhanu M.; Chow, Jennifer; Liese, Andreas; Streit, Wolfgang R.; Wohlgemuth, Roland

doi:10.1002/9783527677122.ch8

Cited by 15 publications

(8 citation statements)

References 172 publications

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“…The exploration of the biocatalytic space has been very useful for the synthesis of metabolites by a systems biocatalysis approach [41]. Selective enzyme-catalyzed Oand N-phosphorylations have been demonstrated as versatile platform technologies and provide various advantages over classical chemical phosphorylations as demonstrated by Sigma-Aldrich/Merck KGaA for the manufacturing of a large variety of phosphorylated metabolites [42][43][44][45][46][47][48][49]. Selective enzymatic water elimination reactions exhibiting full conversion enabled a simple synthetic access to 2-keto-3-deoxysugar acids from easily accessible sugar acids using dehydratases [50][51][52].…”

Section: Exploring the Biocatalytic Spacementioning

confidence: 99%

Biocatalysis in the Swiss Manufacturing Environment

et al. 2020

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Biocatalysis has undergone a remarkable transition in the last two decades, from being considered a niche technology to playing a much more relevant role in organic synthesis today. Advances in molecular biology and bioinformatics, and the decreasing costs for gene synthesis and sequencing contribute to the growing success of engineered biocatalysts in industrial applications [1]. However, the incorporation of biocatalytic process steps in new or established manufacturing routes is not always straightforward. To realize the full synthetic potential of biocatalysis for the sustainable manufacture of chemical building blocks, it is therefore important to regularly analyze the success factors and existing hurdles for the implementation of enzymes in large scale small molecule synthesis. Building on our previous analysis of biocatalysis in the Swiss manufacturing environment [2], we present a follow-up study on how the industrial biocatalysis situation in Switzerland has evolved in the last four years. Considering the current industrial landscape, we record recent advances in biocatalysis in Switzerland as well as give suggestions where enzymatic transformations may be valuably employed to address some of the societal challenges we face today, particularly in the context of the current Coronavirus disease 2019 (COVID-19) pandemic.

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Section: Exploring the Biocatalytic Spacementioning

confidence: 99%

Biocatalysis in the Swiss Manufacturing Environment

et al. 2020

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“…Biocatalytic reaction platforms with numerous biocatalysts and their applications, established over the years for many reaction classes like reductions [40][41] , oxidations [42][43][44] , hydrolysis [45][46] , aminations [47][48] or phosphorylations [49][50] , have paved the way for extending the biocatalyst applications to new substrates and for putting together new synthetic routes. Best practices in the assembly of synthetic biocatalytic as well as chemical synthetic reactions involve rapid prototyping of the most critical reaction steps in order to obtain the first proof-of-principle.…”

Section: Biocatalytic Process Assembly and Prototypingmentioning

confidence: 99%

“…Depending on previous knowledge of the biocatalytic reaction platform, the reaction engineering can work with mathematical optimization tools to define optimum reaction conditions for well-characterized reaction systems, with practical design-of-experiments methodology after prototyping or, if data are lacking, with experimental data acquisition on the characterization of biocatalytic reaction kinetics, biocatalysts, components and thermodynamics of the reaction system as a function of variable parameters 49 . Unfavourable thermodynamics may be overcome by making the reaction irreversible via the utilization of irreversible substrates, different reaction media or the coupling to subsequent irreversible reaction steps.…”

Section: Reaction Engineeringmentioning

confidence: 99%

Biocatalytic Process Design and Reaction Engineering

Wohlgemuth¹

2017

Chem.Biochem.Eng.Q.

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Biocatalytic processes occurring in nature provide a wealth of inspiration for manufacturing processes with high molecular economy. The molecular and engineering aspects of bioprocesses converting available raw materials into valuable products are therefore of much industrial interest. Modular reaction platforms and straightforward working paths, from the fundamental understanding of biocatalytic systems in nature to the design and reaction engineering of novel biocatalytic processes, have been important for shortening development times. Building on broadly applicable reaction platforms and tools for designing biocatalytic processes and their reaction engineering are key success factors. Process integration and intensification aspects are illustrated with biocatalytic processes to numerous small-molecular weight compounds, which have been prepared by novel and highly selective routes, for applications in the life sciences and biomedical sciences.

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“…The thermodynamics of phosphorylation reactions requires overcoming an energy barrier, which may be achieved by changing the reaction environment or by utilizing a high‐energy phosphorus donor. [ 25 ] For straightforward and synthetically useful phosphorylation methods, effective phosphorylating agents, [ 26 ] selective catalytic phosphorylations, [ 27 ] and routes with high molecular economy [ 28 ] are of great importance. Catalytic phosphorylation methods using Lewis acid catalysts or peptide‐based catalysts require protected P(V)‐ or P(III)‐donors, which then need subsequent reaction steps such as selective deprotection or selective oxidation followed by deprotection steps.…”

Section: Introductionmentioning

confidence: 99%

Key advances in biocatalytic phosphorylations in the last two decades: Biocatalytic syntheses in vitro and biotransformations in vivo (in humans)

Wohlgemuth

2020

Biotechnology Journal

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Biocatalytic phosphorylation reactions provide several benefits, such as more direct, milder, more selective, and shorter access routes to phosphorylated products. Favorable characteristics of biocatalytic methodologies represent advantages for in vitro as well as for in vivo phosphorylation reactions, leading to important advances in the science of synthesis towards bioactive phosphorylated compounds in various areas. The scope of this review covers key advances of biocatalytic phosphorylation reactions over the last two decades, for biocatalytic syntheses in vitro and for biotransformations in vivo (in humans). From the origins of probiotic life to in vitro synthetic applications and in vivo formation of bioactive pharmaceuticals, the common purpose is to outline the importance, relevance, and underlying connections of biocatalytic phosphorylations of small molecules. Asymmetric phosphorylations attracting increased attention are highlighted. Phosphohydrolases, phosphotransferases, phosphorylases, phosphomutases, and other enzymes involved in phosphorus chemistry provide powerful toolboxes for resource-efficient and selective in vitro biocatalytic syntheses of phosphorylated metabolites, chiral building blocks, pharmaceuticals as well as in vivo enzymatic formation of biologically active forms of pharmaceuticals. Nature's large diversity of phosphoryl-group-transferring enzymes, advanced enzyme and reaction engineering toolboxes make biocatalytic asymmetric phosphorylations using enzymes a powerful and privileged phosphorylation methodology. K E Y W O R D S chiral building blocks, enzymatic phosphorylation, kinases, metabolites, pharmaceuticals, phosphatases, phosphomutases, phosphoryl-donor, phosphorylases, phosphotransferases 1 INTRODUCTION Biocatalysis and biotransformations involving the element phosphorus are fundamental bioprocesses. The exciting history of the element Abbreviations: API, active pharmaceutical ingredient; FDA, U.S. Food and Drug Administration; P(III)-Donor, donor group containing phosphorus in its oxidation state +3; P(V)-Donor, donor group containing phosphorus in its highest oxidation state +5 phosphorus has been linked to life and death on our planet from its discovery from human urine in 1669 by alchemist Hennig Brand. Many phosphorus bonds to build phosphorus-containing molecules have been synthesized by biocatalytic phosphorylations, either by nature or anthropogenic. [1,2] As many phosphorus-bearing species are structurally stable and functionally reactive, they are also of interest as signals of life and have been detected recently in space. [3,4] The discovery of phosphorus-bearing species in space is of much interest

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Biocatalytic Phosphorylation of Metabolites

Cited by 15 publications

References 172 publications

Biocatalysis in the Swiss Manufacturing Environment

Biocatalysis in the Swiss Manufacturing Environment

Biocatalytic Process Design and Reaction Engineering

Key advances in biocatalytic phosphorylations in the last two decades: Biocatalytic syntheses in vitro and biotransformations in vivo (in humans)

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