Article
Biotechnology & Applied Microbiology
Adrian Tuellinghoff, Harcel Djaya-Mbissam, Joerg Toepel, Bruno Buehler
Summary: The photosynthetic light reaction in cyanobacteria was used to convert cyclohexanone into 6-hydroxyhexanoic acid. Co-expression of Baeyer-Villiger monooxygenase (BVMO) and lactonase from Acidovorax sp. CHX100 enabled the conversion with high activity and without inhibitory accumulation. This study demonstrates the feasibility of light-driven biocatalytic cascade operation in cyanobacteria.
PLANT BIOTECHNOLOGY JOURNAL
(2023)
Article
Chemistry, Multidisciplinary
Magdalena Ripoll, Susana Velasco-Lozano, Erienne Jackson, Eleftheria Diamanti, Lorena Betancor, Fernando Lopez-Gallego
Summary: Biocatalytic cascades can lead to economically sustainable and green processes. By coupling the co-immobilised Gluconobacter oxydans and an isolated transaminase, serinol was successfully synthesized from glycerol with the highest reported titer for non-fermentative biosynthesis. This hybrid heterogeneous biocatalyst also showed promising productivity when starting from industrial by-product crude glycerol, showcasing the potential for valorising bio-based raw materials.
Review
Chemistry, Organic
Nicolctta Gaggero, Domenico C. M. Albanese
Summary: Cascade reactions catalyzed by immobilized multi-enzymatic systems, particularly using combi-CLEAs as a carrier-free immobilization strategy, provide a simple and cost-effective approach to enhance enzyme stability, facilitate biocatalyst recovery and recycling, and enable practical industrial applications at a multigram scale.
CURRENT ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Physical
Yijie Dong, Tang Li, Shiqing Zhang, Joaquin Sanchis, Heng Yin, Jie Ren, Xiang Sheng, Guangyue Li, Manfred T. Reetz
Summary: In this study, the unexpected mechanistic intricacies of Baeyer-Villiger monooxygenases (BVMOs) were discovered, providing insights for expanding their applications in synthetic organic chemistry and biotechnology. The investigation utilized complete mutational deconvolution and experimental construction of a fitness-pathway landscape to elucidate the structural changes of Criegee intermediates and their effects on the evolutionary process.
Review
Chemistry, Physical
Yayati Naresh Palai, Atsushi Fukuoka, Abhijit Shrotri
Summary: This article summarizes the recent developments in catalytic synthesis of C4 chemicals from biomass-derived sugars and their derivatives, and suggests future research directions. C4 chemicals play a vital role in the chemical industry, and sourcing them from biomass can reduce reliance on petrochemicals.
Article
Plant Sciences
Marielle C. Inacio, Weimao Zhong, Ya-Ming Xu, E. M. Kithsiri Wijeratne, Chandrashekhar Madasu, Istvan Molnar, A. A. Leslie Gunatilaka
Summary: Microbial biotransformation of argentatin A, isoargentatin A, and argentatin C, the triterpenoid constituents of guayule resin, was conducted using Chaetomium sp. PA001, an endophytic fungus of the same plant. Six new products were obtained, which formed through nucleophilic oxygenation, lactone ring opening, ring rearrangement, and reduction reactions. The structures of these new products were determined through detailed spectroscopic analysis. None of the products showed antimicrobial activity, but the hydroxy-carboxylic acid derivative of argentatin A exhibited weak cytotoxic activity with improved selectivity against human breast cancer cell line MCF-7 compared to the parent compound. This study reports the first microbial biotransformation of iso-argentatin A and argentatin C.
PHYTOCHEMISTRY LETTERS
(2023)
Article
Multidisciplinary Sciences
Allwin D. McDonald, Peyton M. Higgins, Andrew R. Buller
Summary: SUMS, a method for measuring enzyme activity, can be used to engineer enzymes for a wider range of substrates. This study develops principles for designing and interpreting SUMS assays, providing valuable information for improving enzyme activity, identifying variants, and determining mutational hot-spots.
NATURE COMMUNICATIONS
(2022)
Review
Chemistry, Applied
Ryan M. Phelan, Michael J. Abrahamson, Jesse T. C. Brown, Ruijie K. Zhang, Christian R. Zwick
Summary: Biocatalysis has played an important role in the manufacturing of complex compounds. Lipases, ketoreductases, and transaminases have been widely used as catalysts in API synthesis, but there are still many enzymatic transformations that are not routinely implemented. This article discusses enzyme classes that are increasingly being used in process chemistry and explores the development of scalable, robust, and cost-effective processes. The insights gained from these case studies can guide the development of new catalysts for scalable biotransformations.
ORGANIC PROCESS RESEARCH & DEVELOPMENT
(2022)
Article
Chemistry, Multidisciplinary
Yajiao Zhang, Minjie Liu, Zixin Yang, Juan Lin, Zedu Huang, Fener Chen
Summary: This study achieved the chemoenzymatic asymmetric synthesis of the anabolic-androgenic steroid (+)-boldenone and its prodrug (+)-boldenone undecylenate from a commercially available starting material. The synthesis was accomplished through a cascade enzymatic process in a single Escherichia coli cell, resulting in high yields and demonstrating the potential of flow biocatalysis for industrial production.
Article
Chemistry, Multidisciplinary
Simona Pompei, Christopher Grimm, Christine Schiller, Lukas Schober, Wolfgang Kroutil
Summary: This study demonstrates that demethylating methyl phenyl ethers can be achieved anaerobically using cobalamin-dependent methyltransferases exploiting thiols as a methyl trap. This strategy allows for efficient and high-yielding synthesis of the antioxidant hydroxytyrosol.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Review
Biotechnology & Applied Microbiology
Caroline E. Paul, Daniel Eggerichs, Adrie H. Westphal, Dirk Tischler, Willem J. H. van Berkel
Summary: Flavoprotein monooxygenases (FPMOs) have evolved from model enzymes in mechanistic flavoprotein research to biotechnologically relevant catalysts for sustainable production of valuable chemicals. FPMOs are classified based on protein structural properties and electron donor specificities, with each group catalyzing different types of oxygenation reactions. Engineering strategies have been utilized to enhance the robustness and applicability of FPMOs.
BIOTECHNOLOGY ADVANCES
(2021)
Article
Biotechnology & Applied Microbiology
Paulina Lyczko, Anna Panek, Ireneusz Ceremuga, Alina Swizdor
Summary: Seventeen fungi species were tested for their ability to transform 7-oxo-DHEA, with some strains showing new catalytic activities such as hydroxylation, oxidation, and esterification. Most strains were able to reduce the substrate's oxo group, with two strains achieving complete conversion to a specific alcohol product. Two fungi strains also demonstrated stereospecific reduction capabilities leading to specific hydroxy-DHEA derivatives.
MICROBIAL BIOTECHNOLOGY
(2021)
Article
Chemistry, Organic
Feipeng Liu, Zifan Cheng, Yiyun Fang, Xuchao Wang, Lingzi Zhao, Zi-Qiang Rong
Summary: A metal-controlled divergent protocol for the synthesis of alpha- and beta-substituted gamma-butyrolactones was developed through intramolecular coupling of epoxides with alcohols. This method provides an efficient and practicable way to afford gamma-butyrolactones with good efficiency, excellent regioselectivity, and broad substrate scope.
Article
Biotechnology & Applied Microbiology
Michio Takagi, Kotchakorn T. Sriwong, Ayaka Masuda, Nozomi Kawaguchi, Shusuke Fukui, Lan Huong Le Viet, Dai-Ichiro Kato, Takashi Kitayama, Mikio Fujii, Afifa Ayu Koesoema, Tomoko Matsuda
Summary: This study discovered a novel Baeyer-Villiger monooxygenase (BVMO) and improved its stability through immobilization. This finding is of great significance for the pharmaceutical and chemical industries.
BIOTECHNOLOGY LETTERS
(2022)
Article
Engineering, Chemical
Zhihui Cai, Duo Liu, Jiangnan Huang, Jianning Feng, Hongjuan Wang, Guangxing Yang, Feng Peng, Yonghai Cao, Hao Yu
Summary: A solvent-free, highly efficient, nonmetallic catalytic system was developed using nitrogen-doped carbon nanotubes (NCNTs) as catalyst to synthesize ε-caprolactone (ε-CL) monomer. The NCNTs exhibited significantly higher catalytic activity compared to other carbon catalysts. The presence of oxygen functionalities on the NCNT surface inhibited the activity but unexpectedly increased the efficiency of aldehydes. This study lays the foundation for the industrial application of solvent-free Baeyer-Villiger oxidation catalyzed by nanocarbons.
INDUSTRIAL & ENGINEERING CHEMISTRY RESEARCH
(2022)
Article
Biochemistry & Molecular Biology
Hamid R. Mansouri, Marko D. Mihovilovic, Florian Rudroff
Article
Chemistry, Medicinal
Maria Teresa Iorio, Sabah Rehman, Konstantina Bampali, Berthold Stoeger, Michael Schnuerch, Margot Ernst, Marko D. Mihovilovic
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
(2019)
Review
Biochemistry & Molecular Biology
Blanca Angelica Vega Alanis, Maria Teresa Iorio, Luca L. Silva, Konstantina Bampali, Margot Ernst, Michael Schnuerch, Marko D. Mihovilovic
Article
Biochemistry & Molecular Biology
Toan Dao-Huy, Simone Latkolik, Julia Braeuer, Andreas Pfeil, Hermann Stuppner, Michael Schnuerch, Verena M. Dirsch, Marko D. Mihovilovic
Article
Chemistry, Physical
Simon P. Godehard, Henrik Mueller, Christoffel P. S. Badenhorst, Christian Stanetty, Christoph Suster, Marko D. Mihovilovic, Uwe T. Bornscheuer
Summary: One major challenge in enzymatic synthesis of sugar esters is the low solubility of sugars in toxic organic solvents. This study demonstrated efficient acetylation of sugars in water using engineered acyltransferases, achieving high conversion rates for glucose, maltose, and maltotriose. The discovery of EstA as a promiscuous acyltransferase that preferentially acetylates sugars expands the potential applications of such enzymes in sugar modifications.
Article
Chemistry, Organic
Hubert Kalaus, Alexander Reichetseder, Verena Scheibelreiter, Florian Rudroff, Christian Stanetty, Marko D. Mihovilovic
Summary: A new kinetic method has been developed to accurately determine the minute open-chain content of aldoses, by utilizing the aldehyde-selectivity of a specific reagent to form UV-active adducts. Measurement of simple formation curves and prediction modeling allow for the precise determination of the relative open-chain content of aldoses.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Biochemistry & Molecular Biology
Thomas Linder, Eleni Papaplioura, Diyana Ogurlu, Sophie Geyrhofer, Scarlet Hummelbrunner, Daniel Schachner, Atanas G. Atanasov, Marko D. Mihovilovic, Verena M. Dirsch, Michael Schnuerch
Summary: NF-kappa B inhibitors play a crucial role in inflammation treatment. Through the modification of leoligin, we found that variations in ester functionality and substituents on the tetrahydrofuran scaffold significantly influence the biological activity.
Article
Biochemistry & Molecular Biology
Katharina Obleser, Hubert Kalaus, Bernhard Seidl, Martin Kozich, Christian Stanetty, Marko D. Mihovilovic
Summary: Laccases are environmentally friendly enzymes that provide a green alternative to traditional alcohol oxidation protocols. However, they require mediator molecules to facilitate electron transfer, and there is a lack of comparable data in this field. This study conducted a time-resolved, quantitative screening of laccase and mediator using anis alcohol oxidation as a model reaction. The researchers measured the redox potentials of mediators under the reaction conditions to optimize the mediator-assisted laccase catalyzed oxidations.
Article
Chemistry, Physical
Nadja K. Singer, Katharina Schloegl, J. Patrick Zobel, Marko D. Mihovilovic, Leticia Gonzalez
Summary: Understanding the thermal isomerization mechanism of azobenzene derivatives is crucial for designing photoswitches with adjustable half-lives. Through quantum chemical calculations, nonadiabatic transition state theory, and photosensitized experiments, we unravel the thermal Z/E isomerization of a heteroaromatic azoswitch, phenylazo-1,3,5-trimethylpyrazole, and predict two pathways at room temperature, involving different reaction mechanisms and spin-orbit couplings.
JOURNAL OF PHYSICAL CHEMISTRY LETTERS
(2023)
Article
Chemistry, Physical
Marek Bucko, Peter Gemeiner, Tomas Krajcovic, Marietta Hakarova, Dusan Chorvat, Alzbeta Marcek Chorvatova, Igor Lacik, Florian Rudroff, Marko D. Mihovilovic
Article
Chemistry, Multidisciplinary
Markus Draskovits, Hubert Kalaus, Christian Stanetty, Marko D. Mihovilovic
CHEMICAL COMMUNICATIONS
(2019)
Article
Chemistry, Multidisciplinary
Thomas Linder, Rongxia Liu, Atanas G. Atanasov, Yuanfang Li, Sophie Geyrhofer, Stefan Schwaiger, Hermann Stuppner, Michael Schnurch, Verena M. Dirsch, Marko D. Mihovilovic
Article
Chemistry, Physical
Leticia C. P. Goncalves, Hamid R. Mansouri, Shads PourMehdi, Mohamed Abdellah, Bruna S. Fadiga, Erick L. Bastos, Jacinto Sa, Marko D. Mihovilovic, Florian Rudroffe
CATALYSIS SCIENCE & TECHNOLOGY
(2019)
Article
Chemistry, Physical
Leticia C. P. Goncalves, Hanild R. Mansouri, Erick L. Bastos, Mohamed Abdellah, Bruna S. Fadiga, Jacinto Sa, Florian Rudroff, Marko D. Mihovilovic
CATALYSIS SCIENCE & TECHNOLOGY
(2019)
Correction
Chemistry, Physical
Florian Rudroff, Marko D. Mihovilovic, Harald Groger, Radka Snajdrova, Hans Iding, Uwe T. Bornscheuer
