Fred Höfler

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Before the days of Mechanism, Medicine Schifferl Versenken the one branch of speculative knowledge which had a distinct commercial value. Port Banfrtw. An edict Colleges in the above list, it is not clear, though probable, that the scholars were obliged to live together.

Item Title Wilhelm Höfler. Collection Title Theodore Fred Abel papers. Collector Abel, Theodore Date Created Description Birthdate: ; World War I service: Skibicki , Luquinhas, Pekhart.

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Preliminary product scope of the proposed radioenzymatic reactions. Reaction results shown in black originate from reactions in the absence of formate, whereas results shown in green stem from reactions performed under otherwise identical conditions in the presence of 50 mM NaHCO2.

Reaction conditions: General: the dose rate in each experiment was Detailed experimental and analytical details and further experimental results PDF.

Most electronic Supporting Information files are available without a subscription to ACS Web Editions. Such files may be downloaded by article for research use if there is a public use license linked to the relevant article, that license may permit other uses.

Financial support by the European Research Council ERC Consolidator Grant no. We thank Astrid van de Meer for excellent technical assistance with 60 Co irradiation.

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RETURN TO ISSUE PREV Research Article NEXT. Department of Biotechnology, Delft University of Technology, Van der Maasweg 9, HZ Delft, The Netherlands.

Tianjin Institute of Industrial Biotechnology, Chinese Academy of Sciences, 32 West 7th Avenue, Tianjin Airport Economic Area, Tianjin, China.

More by Wuyuan Zhang. Radiation Science and Technology, Delft University of Technology, Mekelweg 15, JB Delft, The Netherlands.

More by Huanhuan Liu. More by Morten M. More by Peter-Leon Hagedoorn. Department of Biocatalysis, Institute of Catalysis, CSIC, Madrid, Spain.

More by Miguel Alcalde. More by Antonia G. More by Kristina Djanashvili. More by Frank Hollmann. Cite this: ACS Catal.

Publication Date Web : November 20, Publication History Received 14 July Revised 27 October Published online 20 November Published in issue 4 December ACS AuthorChoice with CC-BY-NC-ND license.

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Share on Facebook Twitter WeChat Linked In Reddit Email. PDF 2 MB Get e-Alerts. SUBJECTS: Radiation , Chemical reactions , Peptides and proteins , Genetics , Organic reactions.

Abstract High Resolution Image. Download MS PowerPoint Slide. KEYWORDS: radiation biocatalysis oxyfunctionalization peroxygenases sustainability.

It is known since decades that radiolytic splitting of water results in the formation of various radicals, which eventually form H 2 O 2 and H 2.

Particularly, hydrogen peroxide could be used to drive a broad range of catalytic oxidation reactions. Scheme 1. Peroxygenase Mechanism in a Nutshell; the Resting Fe III —Heme Prosthetic Group Reacts with H 2 O 2 to Form Compound I Cpd I, Fe IV Oxo—Heme Radical Cation ; the Latter can Insert the Activated O Atom Into C—H Bonds 7.

High Resolution Image. In the presence of too high concentrations of H 2 O 2 , however, peroxygenases are also irreversibly inactivated.

The well-known glucose oxidase system, 16,17 for example, transforms glucose into gluconic acid, thereby yielding more than g of waste per mol H 2 O 2 generated.

In this context, the radiolytic formation of H 2 O 2 may represent an interesting alternative method Figure 1 a.

As a radiation source, we used an external gamma radiation source 60 Co, which is widely applied, for example, in radiotherapy i. Indeed, an aqueous buffer placed next to the radiation source steadily accumulated H 2 O 2 up to 0.

In another experiment, we presupplemented the buffer with 0. Apparently, the constant H 2 O 2 concentration was the result of a steady state between H 2 O splitting yielding H 2 O 2 and radiolysis-based splitting of H 2 O 2 yielding H 2 O and O 2.

Next, we combined the 60 Co-induced water radiolysis with a UPO-catalyzed hydroxylation reaction. As a model reaction, we used the selective hydroxylation of ethyl benzene to R phenyl ethanol catalyzed by the recombinant, evolved peroxygenase from Agrocybe aegerita r Aae UPO.

The presence or absence of molecular oxygen had no obvious influence on the product formation rate. Furthermore, performing the reaction in H 2 18 O-enriched buffer resulted in the formation of 18 O-labeled R phenyl ethanol Figure 2 b,c.

This confirms that indeed the reaction medium serves as a source of H 2 O 2 and that reduction of O 2 from ambient air played a minor role in the H 2 O 2 formation.

R phenyl ethanol was the sole product observed, indicating that the selectivity of the biocatalyst was not impaired under the reaction conditions, particularly by the radioactivity.

A control reaction with R phenyl ethanol only under the irradiation showed that radiation-induced further oxidation of the primary enzyme product R phenyl ethanol to acetophenone can be ruled out.

Next, we further investigated some factors influencing the efficiency and robustness of the overall reaction Figure 3.

Increasing the biocatalyst concentration increased the product formation within the first hour Figure 3 a. This increase, however, was not linear and converged to approx.

Interestingly, this product formation rate was approx. This observation can be attributed to the irreversible peroxygenase step removing H 2 O 2 from the steady-state equilibrium.

These experiments, however, also revealed a poor long-term stability of the enzyme under the reaction conditions. Already after 1 h of reaction approx.

This assumption is supported by a considerable decrease in the characteristic Soret peak at nm indicative for an intact heme moiety Figure S3.

Analysis of an inactivated enzyme sample by native gel electrophoresis gave no indication for loss of the quaternary structure Figure S4.

We reasoned that hydroxyl radicals formed during the physicochemical phase of the water radiolysis reaction, for example, the hydroxyl radicals, may oxidatively inactivate the catalytic heme functionality and thereby the biocatalyst.

Of course, also H 2 O 2 -dependent inactivation of the prosthetic group can also contribute to the observed inactivation. However, also the highly H 2 O 2 -stable, 35 V-dependent chloroperoxidase from Curvularia inaequalis Ci VCPO 36 was inactivated under these conditions vide infra.

Suspecting intermediate radical species Figure 1 a as major contributors to the observed biocatalyst inactivation, we tested a range of different radical scavengers Figure 3 b.

Among these radical scavengers especially methanol, acrylamide, and formate enabled significantly increased product formation Figure 3 b.

The effect depended on the concentration of the radical scavenger as exemplified with methanol and formate Figures S5 and S6.

We therefore also compared the time courses of the radioenzymatic reactions in the absence and presence of the radical scavengers methanol and formate Figure 3 c.

Most strikingly, the conversion of ethyl benzene to R phenyl ethanol was increased from approx. In the latter case, a turnover number for the biocatalyst of The dose rate of the radiation source directly influenced the product formation of the radioenzymatic reaction system Table 1.

The final product concentration and directly related to this also the turnover number of the enzyme directly correlated with the dose rate of the radioactivity source applied.

This may be due to a decreased radiolytic H 2 O 2 decomposition at lower dose rates, whereas the biocatalyst concentration remained constant.

Further experiments will be necessary to fully rationalize this observation. Pleasantly, the reactions performed with spent fuel element U also showed good robustness.

Table 1. Radioenzymatic Hydroxylation of Ethyl Benzene Using Different Radiation Sources a. Finally, we initially explored the substrate scope of the proposed radioenzymatic reaction scheme Figure 4.

For this, some further oxyfunctionalization reactions reported for r Aae UPO, such as epoxidation 37 as well as aliphatic 38 and aromatic hydroxylation reactions, were chosen.

Possibly, the radicals present in the reaction mixture lead to racemization of the epoxide product, but further investigations will be necessary to confirm this.

Again, a beneficial effect of formate on the product formation was observed Figure 4. To address the question whether too high H 2 O 2 concentrations may contribute to the abovementioned inactivation of r Aae UPO, we extended the enzyme scope of the proposed radioenzymatic reaction to the vanadium-dependent chloroperoxidase from C.

As H 2 O 2 as a cause for this can be ruled out, we assign this observation to Ci VCPO inactivation by hydroxyl radicals Figure S9. In conclusion, we have demonstrated that radiolytic water splitting can be used to promote biocatalytic oxyfunctionalization reactions.

The dose-rate-dependent steady-state concentration appears ideal to provide heme-dependent peroxygenases with suitable concentrations of H 2 O 2 that enable the reaction while minimizing the oxidative inactivation.

This advantage, at least in the present setup, is compensated by the radical-induced inactivation of the biocatalyst, this is also reflected by the comparably poor performance of the present system compared to other in situ H 2 O 2 generation systems Table S1.

Compared to other radical-generating H 2 O 2 generation systems, the turnover numbers observed here compare very well.

The radical inactivation of the biocatalysts represents an apparent shortcoming of the current setup.

In future experiments, we will address this by physical separation of the biocatalyst from the radiation source. Flow chemistry appears a particularly attractive technical solution.

Although this approach at first sight may appear as a lab curiosity, we believe that it may actually bear some practical relevance.

In this study, we have demonstrated that spent fuel elements can drive peroxygenase-catalyzed reactions. Considering the annually increasing amounts of radioactive waste and its persistence, the proposed radioenzymatic approach may represent a possibility to productively utilize nuclear waste.

Furthermore, it should be kept in mind that globally a variety of different radiation sources are used commercially.

For instance, 60 Co units are used for sterilization and electron beams for various applications and research nuclear reactors more than worldwide.

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