Review
Chemistry, Multidisciplinary
Shuke Wu, Radka Snajdrova, Jeffrey C. Moore, Kai Baldenius, Uwe T. Bornscheuer
Summary: Biocatalysis is widely used as an alternative to chemical catalysis in various fields, with enzymes playing a key role in organic synthesis, particularly in the production of chiral compounds for pharmaceuticals and flavors. Biocatalysts are also utilized on a large scale for the production of specialty and bulk chemicals. This review focuses on scalable chemical production using enzymes, discussing opportunities, limitations, and emerging enzyme classes through illustrative examples.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Physical
Agnieszka Winiarska, Dominik Hege, Yvonne Gemmecker, Joanna Krysciak-Czerwenka, Andreas Seubert, Johann Heider, Maciej Szaleniec
Summary: AOR(Aa) enzyme can catalyze the reduction reaction of organic acids using H-2 as an electron donor, and also catalyze the H-2-dependent reduction reaction of NAD(+) and benzyl viologen. This discovery has potential applications in the design of cascade reactions for the reduction of organic acids to alcohols.
Article
Chemistry, Physical
Xiaowei Li, Yan Zhao
Summary: This study reports the use of molecularly imprinted nanoparticles as catalysts that utilize their environmental chirality to control the stereochemical outcomes. The catalytic reactions conducted in water at room temperature show high yields and excellent enantioselectivity.
JOURNAL OF CATALYSIS
(2022)
Article
Chemistry, Physical
Payel Dowari, Malay Kumar Baroi, Tanushree Das, Basab Kanti Das, Saurav Das, Sumit Chowdhuri, Avinash Garg, Ananya Debnath, Debapratim Das
Summary: Biocatalysis is a significant area of research in modern times, with industries exploring it extensively in order to achieve greener methods for various applications. This study systematically analyzes peptide amphiphiles (PAs) to identify the most effective catalyst with esterase-like activity. Immobilizing catalytic peptides on solid surfaces can lead to the development of cost-effective catalytic formulations.
JOURNAL OF COLLOID AND INTERFACE SCIENCE
(2022)
Article
Chemistry, Physical
Daniel Timelthaler, Christoph Topf
Summary: This study presents a simple method for the transfer hydrogenation of aromatic aldehydes in i-PrOH using the cost-effective and easy-to-handle [Cr(CO)(6)] as a catalyst. The reactions can be carried out in normal atmosphere without the need for special equipment, and various functional groups are tolerated. Furthermore, the addition of TMAO can further promote the catalytic transformations. This method is also suitable for processing thermo-labile substrates.
JOURNAL OF CATALYSIS
(2022)
Article
Chemistry, Multidisciplinary
Timon Schoenauer, Sabrina L. J. Thomae, Leah Kaiser, Mirijam Zobel, Rhett Kempe
Summary: The development of C-N bond formation reactions is crucial in biology and chemistry, with recent progress in 3d metal catalysis showing unique selectivity patterns. By using a novel cobalt catalyst, a catalytic C-N bond formation reaction was successfully reported, utilizing abundant and low-cost starting materials for reductive alkylation.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Organic
Ni Xiong, Yuanqi Dong, Bin Xu, Yang Li, Rong Zeng
Summary: This study describes a mild protocol for amide formation using nitroarenes as nitrogen sources and an inexpensive iron complex as a catalyst. The method utilizes pH-neutral conditions and avoids the use of strong oxidants or reductants, allowing for tolerance of a wide range of aldehydes and nitroarenes with various functional groups.
Article
Chemistry, Physical
Lidia Madalinska, Piotr Kielbasinski, Malgorzata Kwiatkowska
Summary: The enzyme-catalyzed monoacetylation of prochiral bis (2-hydroxymethylphenyl)methylphosphine and bis (2-hydroxymethylphenyl)phenylphosphine and their P-sulfides led to the formation of corresponding monoacetates in a single step, with moderate yields and high enantiomeric excess. The absolute configurations of the selected products were determined, revealing the enzyme's preference for producing compounds with the same spatial arrangement. These newly obtained compounds have potential applications as chiral catalysts/ligands.
Article
Chemistry, Multidisciplinary
Mitchell T. Giordano, Katelyn M. Kitzinger, Pedro de Jesus Cruz, Shubin Liu, Jeffrey S. Johnson
Summary: A bifunctional iminophosphorane (BIMP)-catalyzed method was developed for the synthesis of densely functionalized cyclohexanols via a Michael/aldol domino reaction. The reaction establishes five contiguous stereocenters with high diastereoselection and enantioselectivity. Mechanistic studies revealed the achievement of stereoconvergency through kinetically controlled cyclization after initial diastereodivergent Michael addition. The findings contrast the previously reported crystallization-driven stereoconvergency in similar systems, but the operational attributes remain attractive.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Multidisciplinary
Mingkai Zhang, Peilin Xu, Alex J. Vendola, Christophe Allais, Anne-Marie Dechert Schmitt, Robert A. Singer, James P. Morken
Summary: This paper describes an easily synthesized chiral diazaborolidine that is inexpensive, stable, and exhibits excellent stereoselection across multiple reaction classes. These versatile compounds have utility in four different classes of cycloaddition reactions, offering good yield and stereoselectivity. X-ray structure analysis provides insight into the origin of stereocontrol.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Zlatko Joncev, Christof Sparr
Summary: Alkene metathesis, catalyzed by enantiopure metal alkylidene complexes, provides versatile strategies for producing products with configurationally-defined stereocenters. In this study, the feasibility of alkene metathesis to control stereogenic axes by traceless arene formation was demonstrated. The conversion of stereodynamic trienes into corresponding binaphthalene atropisomers, selectively catalyzed by a chiral molybdenum catalyst, exhibits high enantioselectivity and excellent yields. This approach enables the synthesis of a broad range of molecular topologies with precisely defined configuration.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Applied
Joel P. S. Choo, Richard A. Kammerer, Xiaodan Li, Zhi Li
Summary: The productivity of the whole-cell biocatalytic system was significantly enhanced by using a SUMO tag, leading to a remarkable improvement in the efficiency of phenylacetaldehyde production by the styrene oxide isomerase enzyme.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Multidisciplinary Sciences
Bo-Ran Wang, Yan-Bo Li, Qi Zhang, Dingding Gao, Ping Tian, Qinghua Li, Liang Yin
Summary: A copper(I)-catalyzed asymmetric 1,3-dipolar cycloaddition of azomethine ylides and 1,3-enynes is reported, providing chiral poly-substituted pyrrolidines with high selectivities. 4-aryl-1,3-enynes and 4-silyl-1,3-enynes are suitable dipolarophiles, while 4-alkyl-1,3-enynes are inert. The method is capable of constructing tetrasubstituted stereogenic carbon centers and chiral spiro pyrrolidines. DFT calculations suggest a concerted mechanism. Transformations starting from the pyrrolidine bearing a triethylsilylethynyl group and centered on the alkyne group are achieved.
NATURE COMMUNICATIONS
(2023)
Article
Chemistry, Multidisciplinary
Hui-Fang Huo, Dan Liu, Agula Bao, Tegshi Muschin, Chaolumen Bai, Yong-Sheng Bao
Summary: A highly efficient and stable heterogeneous catalyst with palladium nanoparticles embedded in ordered mesoporous carbon channels was developed for constructing imides from amides using aryl esters as acylation reagents. The catalyst showed excellent catalytic performance and could be reused multiple times without significant decrease in activity.
Article
Chemistry, Multidisciplinary
Mohd Taher, Basudev Maity, Taiki Nakane, Satoshi Abe, Takafumi Ueno, Shyamalava Mazumdar
Summary: The study shows that mutations at the core of the ferritin nanocage can impact the uptake of IrCp*, with mutation of Arg52 by His leading to a significant increase in uptake. Additionally, the ferritin variants were found to exhibit high activity and enantioselectivity in catalyzing transfer hydrogenation reactions.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Editorial Material
Biochemistry & Molecular Biology
Stefano Serra
Review
Chemistry, Physical
Stefano Serra, Davide De Simeis
Review
Infectious Diseases
Davide De Simeis, Stefano Serra
Summary: The discovery of penicillin in 1928 marked the beginning of a new era with antibiotics, with Actinomycetes being the key sources. However, antibiotic resistance is now a major threat, requiring urgent measures to find new antibiotics and change their usage. The role of Actinomycetes in antibiotic history, along with their bioactivities and chemical structures inspiring drug synthesis, are thoroughly described in this review.
Article
Chemistry, Physical
Chiara Allegretti, Francesco G. Gatti, Stefano Marzorati, Letizia Anna Maria Rossato, Stefano Serra, Alberto Strini, Paola D'Arrigo
Summary: The use of Reactive Deep Eutectic Solvents (RDESs) as reaction media for the preparation of polar head modified phospholipids (PLs) through phospholipase D (PLD)-catalyzed transphosphatidylations has been investigated. The designed RDESs actively participate in the synthetic processes as reagents, leading to optimized yields of PLs in a sustainable process implementation.
Article
Chemistry, Physical
Stefano Serra, Davide De Simeis, Stefano Marzorati, Mattia Valentino
Summary: The recombinant oleate hydratase from Lactobacillus rhamnosus ATCC 53103 was found to be completely inactive without the presence of a large amount of FAD, but could be activated by FADH(2) to be at least one hundred times more active. This discovery led to the development of a preparative procedure for the stereoselective synthesis of (R)-10-hydroxystearic acid, with a high yield and easy recovery process through simple filtration.
Article
Chemistry, Multidisciplinary
Chiara Allegretti, Andrea Bono, Paola D'Arrigo, Francesco G. Gatti, Stefano Marzorati, Letizia A. M. Rossato, Stefano Serra, Alberto Strini, Davide Tessaro
Summary: This study demonstrates the conversion of acid degumming waste from the seeds oil refining industry into value-added phospholipids through enzymatic reaction, providing a sustainable approach for the production of functional food and nutraceutical ingredients. This alternative process not only adds greater value in terms of carbon recycling, but also aligns with the principles of bioeconomy in promoting the wiser reuse of renewable resources within a circular economy perspective.
Article
Chemistry, Physical
Stefano Serra, Stefano Marzorati, Mattia Valentino
Summary: Two biotechnological processes for producing dihydrocoumarin were described, one utilizing yeast and the other involving a series of enzymes. While microbial reduction is simple but has low yield, the enzymatic approach is more efficient but requires specific enzymes.
Article
Biochemistry & Molecular Biology
Annarita Stringaro, Stefano Serra, Alessandro Gori, Annarica Calcabrini, Marisa Colone, Maria Luisa Dupuis, Francesca Spadaro, Serena Cecchetti, Alberto Vitali
Summary: This study analyzed the cell specificity, cell viability effects, intracellular distribution, and immune cell response of a new peptide conjugate of Aloe-emodin in SKBR3 and A549 cell lines. The results showed that the conjugate was more effective at reducing cell viability than AE in both cell lines, with a nuclear localization in SKBR3 cells and cytoplasmic distribution in A459 cells.
Article
Biochemistry & Molecular Biology
Chiara Allegretti, Emanuela Bellinetto, Paola D'Arrigo, Monica Ferro, Gianmarco Griffini, Letizia Anna Maria Rossato, Eleonora Ruffini, Luca Schiavi, Stefano Serra, Alberto Strini, Stefano Turri
Summary: In this study, rice husks were completely utilized through environmentally friendly pretreatment and fractionation methods. It was found that lignins obtained from both raw and parboiled rice husks had similar characteristics and showed potential as alternatives to cement water reducers. However, both raw and parboiled rice husks demonstrated poor performance as microbiological growth substrates. This study provides a promising strategy for the circular economy utilization of rice industry waste.
Article
Chemistry, Physical
Stefano Serra, Antonio Castagna, Stefano Marzorati, Mattia Valentino
Summary: This study investigated the biotransformation of phenylalanine, tyrosine, and tryptophan by yeast strains belonging to the Yarrowia genus. The results showed that under high aerobic conditions, these microorganisms primarily converted phenylalanine and tyrosine into phenylacetic acid and 4-hydroxyphenylacetic acid, respectively, while tryptophan was mainly transformed into anthranilic acid by Y. lipolytica. The findings suggest that the natural flavor compound, phenylacetic acid, can be produced on a large scale through the Yarrowia strains-mediated biotransformation of natural phenylalanine.
Article
Medicine, Research & Experimental
Donatella Lucchetti, Francesca Luongo, Enrico Gurreri, Filomena Colella, Giulia Artemi, Claudia Desiderio, Stefano Serra, Felice Giuliante, Ruggero De Maria, Alessandro Sgambato, Alberto Vitali, Micol Eleonora Fiori
Summary: Colorectal cancer (CRC) is the second leading cause of cancer death, with a high mortality rate. This study focused on the potential anticancer activity of a natural compound called Metachromins V (MV) derived from marine sponges on patient-derived CRC-CSCs. MV showed strong cytotoxic effects on CSCs regardless of their mutational background, affecting cell cycle progression, cytoskeleton organization, and the expression of specific molecules involved in CRC-CSCs motility and invasion.
BIOMEDICINE & PHARMACOTHERAPY
(2023)
Article
Chemistry, Multidisciplinary
Letizia Anna Maria Rossato, Mohammad Morsali, Eleonora Ruffini, Pietro Bertuzzi, Stefano Serra, Paola D'Arrigo, Mika Sipponen
Summary: Immobilization of phospholipase D (PLD) on lignin nanoparticles by direct adsorption has been used for the preparation of high-value polar head-modified phospholipids. This method is characterized by high stability and recyclability, making it an environmentally friendly biocatalyst.
Article
Biotechnology & Applied Microbiology
Chiara Allegretti, Emanuela Bellinetto, Paola D'Arrigo, Gianmarco Griffini, Stefano Marzorati, Letizia Anna Maria Rossato, Eleonora Ruffini, Luca Schiavi, Stefano Serra, Alberto Strini, Davide Tessaro, Stefano Turri
Summary: This study recovered brewers' spent grain and successfully utilized it through fractionation. The soluble proteins and sugars were separated for microbial fermentation and valuable product preparation. The solid residue was fractionated using a deep eutectic solvent, resulting in cellulose and lignin. This strategy shows promise for the circular economy utilization of brewers' spent grain.
FERMENTATION-BASEL
(2022)
Article
Chemistry, Multidisciplinary
Stefano Serra, Davide De Simeis, Sara Papili
Summary: This work presents a user-friendly procedure for preparing all isomeric forms of terpene linalool oxide, involving transformation, separation, and hydrolysis steps. The unique mandatory requirement of this method is the availability of both enantiomers of linalool, allowing for convenient operation from a milligram to multigram scale.
CHEMISTRY-SWITZERLAND
(2021)
Article
Chemistry, Multidisciplinary
Davide De Simeis, Stefano Serra, Alessandro Di Fonzo, Francesco Secundo
Summary: The study investigated the role of microalgae in synthesizing high-value flavors and fragrances, but found that the microalgal strains used were not responsible for substrate oxidation, which was actually a photochemical reaction involving oxygen as the oxidant. These findings suggest a new possible strategy to easily obtain nootkatone in a natural way using just an aqueous medium, oxygen, and light, despite casting a shadow on the industrial use of these microorganisms.
CHEMISTRY-SWITZERLAND
(2021)
