One-pot enzymatic reaction sequence for the syntheses of d-glyceraldehyde 3-phosphate and l-glycerol 3-phosphate

Molla, Getachew Shibabaw; Wohlgemuth, Roland; Liese, Andreas

doi:10.1016/j.molcatb.2015.12.004

Cited by 10 publications

(10 citation statements)

References 41 publications

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“…Triosephosphate metabolites such as dihydroxyacetone phosphate (DHAP) and DL‐GAP are unstable at neutral and alkaline pH conditions . The instability of L‐GAP at nearly neutral pH conditions is a critical factor for a biocatalytic process development using glycerol kinase from Cellulomonas sp., because the enzyme shows no activity at pH below 4, while L‐GAP is stable at pH below 4.…”

Section: Resultsmentioning

confidence: 99%

“…Triosephosphate metabolites such as dihydroxyacetone phosphate (DHAP) and DL-GAP are unstable at neutral and alkaline pH conditions [8,15,[18][19][20][21]. The instability of L-GAP at nearly neutral pH conditions is a critical factor for a biocatalytic process development using glycerol…”

Section: Product Instabilitymentioning

confidence: 99%

“…Phosphorylated metabolites such as L-glyceraldehyde-3-phosphate (L-GAP) are synthetically useful to design in vitro single-pot cascade biocatalytic reaction sequences using enzymes such as aldolases or transketolases [6][7][8][9][10]. L-GAP has been described to have a bactericidal effect on Escherichia coli while D-GAP does not have the same effect [11].…”

Section: Introductionmentioning

confidence: 99%

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Bioreaction Engineering Leading to Efficient Synthesis of L‐Glyceraldehyd‐3‐Phosphate

Molla

Kinfu

Chow

et al. 2017

Biotechnology Journal

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Enantiopure L-glyceraldehyde-3-phosphate (L-GAP) is a useful building block in natural biological and synthetic processes. A biocatalytic process using glycerol kinase from Cellulomonas sp. (EC 2.7.1.30) catalyzed phosphorylation of L-glyceraldehyde (L-GA) by ATP is used for the synthesis of L-GAP. L-GAP has a half-life of 6.86 h under reaction conditions. The activity of this enzyme depends on the Mg to ATP molar ratio showing maximum activity at the optimum molar ratio of 0.7. A kinetic model is developed and validated showing a 2D correlation of 99.9% between experimental and numerical data matrices. The enzyme exhibits inhibition by ADP, AMP, methylglyoxal and Ca , but not by L-GAP and inorganic orthophosphate. Moreover, equal amount of Ca exerts a different degree of inhibition relative to the activity without the addition of Ca depending on the Mg to ATP molar ratio. If the Mg to ATP molar ratio is set to be at the optimum value or less, inorganic hexametaphosphate (PPi6) suppresses the enzyme activity; otherwise PPi6 enhances the enzyme activity. Based on reaction engineering parameters such as conversion, selectivity and specific productivity, evaluation of different reactor types reveals that batchwise operation via stirred-tank reactor is the most efficient process for the synthesis of L-GAP.

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Section: Resultsmentioning

confidence: 99%

Section: Product Instabilitymentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Bioreaction Engineering Leading to Efficient Synthesis of L‐Glyceraldehyd‐3‐Phosphate

Molla

Kinfu

Chow

et al. 2017

Biotechnology Journal

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“…The intensification of a biocatalytic process for a selected route and the level of integration depends on the limiting step in the process design and needs to consider its debottlenecking (Figure ) with the development of the optimum reaction conditions with high substrate concentrations and low enzyme concentrations, the scaling concept, the type of reactor and subsequent operations for the optimum performance of a robust and stable overall process with high space‐time yield . Analysing the reaction kinetics, enzyme inhibition, instable products and other process bottlenecks has been useful for selecting the most suitable reaction conditions and reactor type, as shown in the case of the synthesis of glyceraldehyde‐3‐phosphates . The common inhibition of enzymatic reactions by substrates, products or byproducts can be overcome by a number of different approaches, such as using solid adsorbents for substrate and product inhibition, protecting reactive aldehyde groups as dimethylacetals or utilizing an enzymatic reaction for removing an inhibiting byproduct .…”

Section: Process and Reaction Engineeringmentioning

confidence: 99%

Horizons of Systems Biocatalysis and Renaissance of Metabolite Synthesis

Wohlgemuth¹

2018

Biotechnol. J.

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The small molecule domain of biological cellular systems is closely related to the synthesis and breakdown of larger molecules such as DNA, RNA, proteins, or polysaccharides. Although the analysis, identification, characterization and synthesis of metabolites has a long history of milestone discoveries, it continues to be of great interest in the search for novel biological activities, metabolic pathways, diagnostic and therapeutic applications. Biologically active metabolites benefit from advantages in diffusion and transport for various interactions with proteins and nucleic acids and regulatory events. Therefore, metabolism is receiving renewed interest and meets molecular biology in the context of a true molecular understanding of cellular systems in health and disease. The analysis of the spatial and temporal organization of biocatalysis in cellular and subcellular systems provides valuable clues for resource- and energy-efficient synthetic routes to natural metabolites. At the same time metabolites are needed for these analyses and the synthesis of metabolites is experiencing a renaissance. A Systems Biocatalysis approach to the synthesis of metabolites aims at biocatalytic route designs with high molecular economy. Biocatalytic reaction platforms have been successfully developed as preferred synthetic methodology for a number of reaction classes, which can be assembled in the selection of routes to metabolites.

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“…In cases of stability mismatches between substrate or product stabilities and enzyme activities and stabilities, rapid progress can be obtained by optimizing process windows 58 . Further optimization of reaction engineering parameters, such as the degree of conversion, selectivity, and specific productivity, require more work, but can lead to highly efficient synthetic procedures [59][60] . In addition to high space-time yield, reaction engineering and process intensification aim at complete conversion to the final product in order to avoid laborious product isolation operations [61][62][63] .…”

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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One-pot enzymatic reaction sequence for the syntheses of d-glyceraldehyde 3-phosphate and l-glycerol 3-phosphate

Cited by 10 publications

References 41 publications

Bioreaction Engineering Leading to Efficient Synthesis of L‐Glyceraldehyd‐3‐Phosphate

Bioreaction Engineering Leading to Efficient Synthesis of L‐Glyceraldehyd‐3‐Phosphate

Horizons of Systems Biocatalysis and Renaissance of Metabolite Synthesis

Biocatalytic Process Design and Reaction Engineering

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