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β-Phenylalanine Ester Synthesis from Stable β-Keto Ester Substrate Using Engineered ω-Transaminases
(2018)
Fatty aldehydes (FALs) can be derived from fatty acids (FAs) and related compounds and are frequently used as flavors and fragrances. Although chemical methods have been conventionally used, their selective biotechnological production aiming at more efficient and eco-friendly synthetic routes is in demand. α-Dioxygenases (α-DOXs) are heme-dependent oxidative enzymes biologically involved in the initial step of plant FA α-oxidation during which molecular oxygen is incorporated into the Cα-position of a FA (Cn) to generate the intermediate FA hydroperoxide, which is subsequently converted into the shortened corresponding FAL (Cn-1). α-DOXs are promising biocatalysts for the flavor and fragrance industries, they do not require NAD(P)H as cofactors or redox partner proteins, and they have a broad substrate scope. Here, we highlight recent advances in the biocatalytic utilization of α-DOXs with emphasis on newly discovered cyanobacterial α-DOXs as well as analytical methods to measure α-DOX activity in vitro and in vivo.
This text is designed to give the reader a helping hand in writing a scientific paper. It provides generic advice on ways that a scientific paper can be improved. The focus is on the following ethical and non-technical issues: (1) when to start writing, and in what language; (2) how to choose a good title; (3) what should be included in the various sections (abstract, introduction, experimental, results, discussion, conclusions, and supporting information (supplementary material); (4) who should be considered as a co-author, and who should be acknowledged for help; (5) which journal should be chosen; and (6) how to respond to reviewers’ comments. Purely technical issues, such as grammar, artwork, reference styles, etc., are not considered.
This thesis deals with the process considerations and optimizations of a whole-cell enzyme cascade reaction for the synthesis of ɛ-caprolactone. The enzyme cascade synthesis of ɛ-caprolactone has been conceptualized and verified using a dehydrogenase and a monooxygenase. The advantage of this enzyme combination is the closed-loop co-factor regeneration. Dehydrogenase and monooxygenase expressed in discrete whole cells were applied in defined ratio to conceptualize the cascade reaction. This necessitates the use of separate co-factor regeneration system due to impermeability of the E. coli cell wall to the co-factor. Article I deal with the design and optimization of dehydrogenase and monooxygenase co-expression in a same E. coli cell. In Article II, the cascade reaction was upscaled and a fed-batch process was realized. Following which, the important reaction metrices were analyzed and optimized. Article III extends the two-enzyme cascade with a lipase. The use of lipase helps to overcome the product inhibition of monooxygenase by ɛ-caprolactone.
Abstract
Desulfarculus baarsii and Desulfurivibrio alkaliphilus are strictly anaerobic bacteria existing in marine sediments. D. baarsii gains energy through reducing sulphate and D. alkaliphilus is able to reduce elemental sulphur, thiosulphate and polysulphide in seawater. Both organisms were previously identified as key organisms in sediment derived, bidirectional electroactive biofilms. Here, we investigated the electrochemical performance of these two bacteria in bio‐electrochemical systems and their possible involvement in anodic and cathodic reactions. The results show that D. baarsii was unable to donate or accept electrons to/from an electrode, while D. alkaliphilus was able to catalyse both anodic and cathodic reactions and interact with the electrode through direct or potentially indirect electron transfer. Raman spectra of D. alkaliphilus electrode biofilms showed a high similarity to Geobacter sulfurreducens biofilms, including the specific bands of cytochromes b and c, explaining the electroactivity of D. alkaliphilus in bioelectrochemical reactions.
Enzymatic degradation and recycling can reduce the environmental impact of plastics. Despite decades of research, no enzymes for the efficient hydrolysis of polyurethanes have been reported. Whereas the hydrolysis of the ester bonds in polyester‐polyurethanes by cutinases is known, the urethane bonds in polyether‐polyurethanes have remained inaccessible to biocatalytic hydrolysis. Here we report the discovery of urethanases from a metagenome library constructed from soil that had been exposed to polyurethane waste for many years. We then demonstrate the use of a urethanase in a chemoenzymatic process for polyurethane foam recycling. The urethanase hydrolyses low molecular weight dicarbamates resulting from chemical glycolysis of polyether‐polyurethane foam, making this strategy broadly applicable to diverse polyether‐polyurethane wastes.
Marine algae produce complex polysaccharides, which can be degraded by marine heterotrophic bacteria utilizing carbohydrate-active enzymes. The red algal polysaccharide porphyran contains the methoxy sugar 6-O-methyl-D-galactose (G6Me). In the degradation of porphyran, oxidative demethylation of this monosaccharide towards D-galactose and formaldehyde occurs, which is catalyzed by a cytochrome P450 monooxygenase and its redox partners. In direct proximity to the genes encoding for the key enzymes of this oxidative demethylation, genes encoding for zinc-dependent alcohol dehydrogenases (ADHs) were identified, which seem to be conserved in porphyran utilizing marine Flavobacteriia. Considering the fact that dehydrogenases could play an auxiliary role in carbohydrate degradation, we aimed to elucidate the physiological role of these marine ADHs. Although our results reveal that the ADHs are not involved in formaldehyde detoxification, a knockout of the ADH gene causes a dramatic growth defect of Zobellia galactanivorans with G6Me as a substrate. This indicates that the ADH is required for G6Me utilization. Complete biochemical characterizations of the ADHs from Formosa agariphila KMM 3901T (FoADH) and Z. galactanivorans DsijT (ZoADH) were performed, and the substrate screening revealed that these enzymes preferentially convert aromatic aldehydes. Additionally, we elucidated the crystal structures of FoADH and ZoADH in complex with NAD+ and showed that the strict substrate specificity of these new auxiliary enzymes is based on a narrow active site.
Abstract
This work presents the reactivity and dissolution of an as‐polished and electrochemically pre‐treated polycrystalline Au electrode, which is used as a model system. The effect of the electrochemical pre‐treatment in corrosive 0.37 M HCl solutions on the Au surface roughness and dissolution is investigated by varying the number of pre‐treatment steps at 1.16 V against the reversible hydrogen electrode. It is shown that the first 10 s pre‐treatment of the as‐polished Au results in a higher surface roughness and thus higher electrochemically active surface area (ECSA) than that of the as‐polished Au. With the subsequent pre‐treatments, however, the ECSA is gradually decreasing reaching a steady value. The dissolution rate of the pre‐treated Au electrodes upon potential cycling in 0.1 M H2SO4 is determined by in situ inductively coupled plasma mass spectrometry. A non‐linear dependence of Au dissolution amount is found with respect to the number of pre‐treatments. The overall total Au dissolution rate follows a similar trend as ECSA/roughness. However, an important difference in the dissolution behavior is identified with respect to dissolution processes during Au oxidation (anodic dissolution) and Au reduction (cathodic dissolution): the former is more sensitive to the surface roughness. Thus, the ratio between Au anodic and cathodic dissolution amounts decreases substantially with decrease in surface roughness. This finding is explained by the slow and fast dissolution kinetics for anodic and cathodic processes, respectively. Current work further advances our understanding of the complex Au dissolution mechanism.
Abstract
In the RNA world, the exchange of sequence patches between two RNAs is an intriguing evolutionary concept, allowing generation of new RNA molecules with novel functionality. Based on the hairpin ribozyme (HPR) with its unique cleavage‐ligation properties, we here demonstrate RNA supported RNA recombination as a possible scenario for the emergence of larger RNA molecules with more complex functionality. A HPR variant designed for the purpose of recombination is capable of cleaving two different RNA molecules, one being a hammerhead ribozyme (HHR) and the other an aptamer (A), and to subsequently recombine and ligate the resulting fragments to a hammerhead ribozyme that is allosterically controlled (HHA) by a cognate ligand. Two such recombination processes involving aptamers for either theophylline or flavine mononucleotide (FMN) are demonstrated with yields of functional recombination product of up to 34 %.
Abstract
A device for the transaminase‐catalysed synthesis combined with continuous recovery of chiral amines was designed. The system enabled the separation of the reaction components in three liquid phases: a reaction phase, an organic solvent phase (where the poorly water soluble ketone substrate was supplied), and an aqueous extraction phase for continuous product recovery. The transaminase‐mediated asymmetric synthesis of (S)‐1‐methyl‐3‐phenylpropylamine was employed as model reaction. Factors influencing the performance of the system, such as reactor geometry, working volumes and operating parameters, were investigated. Specifically, reaction yield and product recovery were enhanced by i) reducing the thickness of the reaction phase, while continuously stirring and ii) reducing the volume of the extraction phase. Under the optimal condition tested, 85 % of the product formed was extracted and a product concentration value of 9 g/L was reached. However, co‐extraction of the unreacted amine donor (17 %) was observed. Advantages and drawbacks of this process compared to existing technologies, as well as possible optimization strategies are discussed.