Article
Multidisciplinary Sciences
Bob J. Ignacio, Jelmer Dijkstra, Natalia Mora, Erik F. J. Slot, Margot J. van Weijsten, Erik Storkebaum, Michiel Vermeulen, Kimberly M. Bonger
Summary: THRONCAT is a threonine-derived non-canonical amino acid tagging method based on bioorthogonal threonine analog beta-ethynylserine (beta ES), which enables efficient labeling of the nascent proteome in complete growth media within minutes. It can be used in bacteria, mammalian cells, and Drosophila melanogaster, and has the potential to address diverse biological questions.
NATURE COMMUNICATIONS
(2023)
Article
Biotechnology & Applied Microbiology
Jingqi Chen, Oscar P. Kuipers
Summary: This study reinforces the importance of a well-installed LanBTC complex in the cell membrane for the biosynthesis and transport of lanthipeptides. The recruitment of SpaT from the peripheral cell membrane to the cell poles by the NisBC complex in L. lactis was observed, which may explain the mechanism by which the secretion of the premature peptide is prevented.
APPLIED AND ENVIRONMENTAL MICROBIOLOGY
(2022)
Article
Chemistry, Organic
Lani J. Davies, Laura M. Shuttleworth, Xiaobai Zhang, Sherry Peng, Christoph Nitsche
Summary: The biocompatible synthesis of constrained peptides is achieved by a straightforward method to introduce N-terminal ketones and aminooxy side chains during solid-phase peptide synthesis. Cyclization occurs spontaneously after acidic cleavage or in aqueous buffer. Protease inhibitors with varying conformational constraint are successfully synthesized, and the most constrained peptide exhibits an activity 2 orders of magnitude higher than its linear analog.
Review
Chemistry, Multidisciplinary
Stefano Fedeli, Jungkyun Im, Sanjana Gopalakrishnan, James L. Elia, Aarohi Gupta, Dongkap Kim, Vincent M. Rotello
Summary: Bioorthogonal transformations are chemical reactions that use pathways inaccessible to biological processes, providing new approaches for imaging and therapeutic strategies. Transition metal catalysts are widely employed as bioorthogonal catalysts, but face challenges in direct application in living systems, which can be addressed by incorporating them into nanomaterial scaffolds.
CHEMICAL SOCIETY REVIEWS
(2021)
Article
Chemistry, Multidisciplinary
Lili Xia, Meng Chen, Caihong Dong, Feipeng Liu, Hui Huang, Wei Feng, Yu Chen
Summary: In this study, a versatile bioorthogonal catalyst based on ultrasmall poly(acrylic acid)-modified copper nanocomplexes (Cu@PAA NCs) is established for high spatiotemporal catalytic efficacy. The catalytic activity of Cu@PAA NCs can be reversibly regulated via valence state interconversion under exogenous ultrasound irradiation, enabling off-target prodrug activation in lesion sites. Additionally, Cu@PAA NCs exhibit robust sonosensitizing ability for sonodynamic therapy and enhanced contrast in magnetic resonance and photoacoustic imaging. The intrinsically benign biocompatibility of renal-clearable Cu@PAA NCs further highlights their potential in disease theranostics.
ADVANCED MATERIALS
(2023)
Review
Biochemistry & Molecular Biology
Karine Porte, Maxime Riberaud, Remi Chatre, Davide Audisio, Sebastien Papot, Frederic Taran
Summary: The advent of bioorthogonal chemistry has enabled ambitious applications of unnatural chemical reactions within living organisms, a long-sought goal in chemical biology. This review highlights the progress in understanding fundamental biological processes and the development of novel imaging and therapeutic strategies using bioorthogonal chemistry in animal models.
Article
Chemistry, Multidisciplinary
Athanasios Markos, Maurice Biedermann, Johannes Heimgartner, Adeline Schmitt, Kathrin Lang, Helma Wennemers
Summary: In this study, C,N-cyclic-N'-acyl azomethine imines (AMIs) were introduced to bioorthogonal reactions in an aqueous environment, showing stability under physiological conditions and selective reactivity with isonitriles. The AMI-isonitrile ligation demonstrated biocompatibility and orthogonality to commonly used bioorthogonal reactions.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Biochemical Research Methods
Qingxin Yao, Feng Lin, Chenghao Lu, Ruijia Zhang, Hanlin Xu, Xiaoqian Hu, Ziyang Wu, Yuan Gao, Peng R. Chen
Summary: This article introduces a dual-mechanism targeted bioorthogonal prodrug therapy that utilizes two orthogonal, receptor-independent tumor-targeting strategies to maximize therapeutic efficacy and minimize adverse drug reactions for anticancer therapies.
BIOCONJUGATE CHEMISTRY
(2023)
Review
Chemistry, Multidisciplinary
Rui Huang, Cristina-Maria Hirschbiegel, Victor Lehot, Liang Liu, Yagiz Anil Cicek, Vincent M. Rotello
Summary: This review provides an overview of recent advances in the field of bioorthogonal nanozymes, focusing on the modular design of nanomaterials and catalysts and their synergistic engineering for in situ uncaging of imaging and therapeutic agents. Bioorthogonal nanozymes enable in situ drug synthesis at disease sites through prodrug activation. The role of nanomaterials in stabilizing and regulating transition metal catalysts is investigated, emphasizing their modular design.
ADVANCED MATERIALS
(2023)
Article
Chemistry, Organic
Fayang Xie, Haolin Jiang, Xiangqian Jia, Jingyang Zhang, Zhu Zhu, Juanjuan Du, Yefeng Tang
Summary: Here, we report a novel bioorthogonal reaction based on bridgehead alkene catalyzed inverse electron-demand Diels-Alder cycloaddition. This reaction exhibits high reactivity and excellent biocompatibility. The developed reaction has been successfully applied to in vitro protein labeling and pretargeted live cell imaging.
Article
Multidisciplinary Sciences
Anna Cioce, Beatriz Calle, Tatiana Rizou, Sarah C. Lowery, Victoria Bridgeman, Keira E. Mahoney, Andrea Marchesi, Ganka Bineva-Todd, Helen Flynn, Zhen Li, Omur Y. Tastan, Chloe Roustan, Pablo Soro-Barrio, Thomas M. Wood, Tessa Keenan, Peter Both, Kun Huang, Fabio Parmeggiani, Ambrosius P. Snijders, Mark Skehel, Svend Kjaer, Martin A. Fascione, Carolyn R. Bertozzi, Sabine Flitsch, Stacy A. Malaker, Ilaria Malanchi, Benjamin Schumann, Mahmoud-Reza Rafiee, Acely Garza-Garcia, Aristotelis Antonopoulos, Stuart M. Haslam
Summary: In this study, a strategy called BOCTAG was developed to label glycoproteins by equipping cells with an artificial biosynthetic pathway. The method was demonstrated to be applicable in co-culture and mouse models, allowing for the annotation of cell-specific glycosylation sites.
NATURE COMMUNICATIONS
(2022)
Review
Chemistry, Multidisciplinary
Madonna M. A. Mitry, Francesca Greco, Helen M. I. Osborn
Summary: Bioorthogonal chemistry involves selective biocompatible reactions between functional groups that are not normally present in biology. It has been used to probe biomolecules in living systems, and has advanced biomedical strategies such as diagnostics and therapeutics. This review discusses challenges and opportunities in translating in vitro bioorthogonal approaches to in vivo settings, focusing on methods to deliver the bioorthogonal reaction components, and critically appraises the suitability of these reactions for in vivo applications.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Review
Biochemical Research Methods
Robert E. Bird, Steven A. Lemmel, Xiang Yu, Qiongqiong Angela Zhou
Summary: Bioorthogonal chemistry is a method using non-native functional groups to explore biology in living organisms. This review summarizes common reactions in bioorthogonal methods and the frequency of bioorthogonal applications on different types of biomolecules. The application of bioorthogonal chemistry in imaging, drug delivery, and protein surface attachment is discussed, highlighting its current limitations and potential for future productive use.
BIOCONJUGATE CHEMISTRY
(2021)
Article
Engineering, Biomedical
Xianzhi Zhang, Ryan F. Landis, Puspam Keshri, Roberto Cao-Milan, David C. Luther, Sanjana Gopalakrishnan, Yuanchang Liu, Rui Huang, Gengtan Li, Morgane Malassine, Imad Uddin, Brayan Rondon, Vincent M. Rotello
Summary: Bioorthogonal catalysis is a promising strategy for imaging and therapeutic applications, with the use of a polymeric scaffold to encapsulate transition metal catalysts resulting in bioorthogonal polyzymes that enhance stability and demonstrate therapeutic potential by transforming a nontoxic prodrug into an anticancer drug.
ADVANCED HEALTHCARE MATERIALS
(2021)
Review
Biochemistry & Molecular Biology
Gaoxiang Zhao, Zhutie Li, Renshuai Zhang, Liman Zhou, Haibo Zhao, Hongfei Jiang
Summary: Bioorthogonal chemistry represents highly efficient and biocompatible reactions that proceed selectively and rapidly in biological situations. Tetrazine bioorthogonal reactions play an important role in in vivo imaging applications, allowing for the easy tracking of real signals through controlled fluorescence or radiation off-on mechanism.
FRONTIERS IN MOLECULAR BIOSCIENCES
(2022)
Article
Chemistry, Multidisciplinary
Roos C. W. van Lier, A. Dowine de Bruijn, Gerard Roelfes
Summary: The study demonstrates a selective photocatalytic modification method for dehydroalanine residues in proteins and peptides, using a new water-soluble iridium(III) photoredox catalyst. This work suggests that photoredox catalysis using the newly designed catalyst is a promising strategy and could have great potential for novel bioconjugation strategies involving natural products containing dehydroalanine.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Multidisciplinary
Reinder H. de Vries, Jakob H. Viel, Oscar P. Kuipers, Gerard Roelfes
Summary: This study describes the fast and selective chemical editing of ribosomally synthesized and post-translationally modified peptides (RiPPs) through beta-borylation of dehydroalanine residues. The method efficiently modifies various peptides, increasing their water solubility and maintaining antimicrobial activity. Additionally, the introduced boronic acid functionalities can be used for chemical mutagenesis and pH-controlled labeling of RiPPs.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Shreyans Chordia, Siddarth Narasimhan, Alessandra Lucini Paioni, Marc Baldus, Gerard Roelfes
Summary: The study demonstrates the supramolecular assembly of ArMs in E. coli cells and their application in enzyme catalysis. Improved mutants were obtained through directed evolution, and the whole-cell ArM system showed catalytic activity without the need for engineering.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Physical
Ruben V. Maaskant, Shreyans Chordia, Gerard Roelfes
Summary: The research focused on combining transition-metal catalysis with whole-cell biocatalysis to derivatize styrene. Using ruthenium and palladium catalysts, different product derivatives could be obtained from the whole-cell biosynthesis of styrene.
Article
Biochemistry & Molecular Biology
Aditya Iyer, Maxim Baranov, Alexander J. Foster, Shreyans Chordia, Gerard Roelfes, Rifka Vlijm, Geert van den Bogaart, Bert Poolman
Summary: The study developed noncovalent fluorogenic protein tags in bacteria using transcription factor-based tags, CTPEs, to enable long-term fluorescence microscopy of living bacterial cells. This provides a general tool for investigating cellular protein localization and dynamics, protein-protein interactions, and prolonged live-cell microscopy, even under oxygen-free conditions.
ACS CHEMICAL BIOLOGY
(2021)
Article
Biochemistry & Molecular Biology
Gerard Roelfes
Summary: Heme enzymes are versatile catalysts in nature and can catalyze reactions where there are no equivalents in nature. Approaches to create enzymes for cyclopropanation include repurposing of heme enzymes, strategies to improve these enzymes, and artificial heme enzymes. Lessons learned from mechanism and design principles are discussed in this review.
JOURNAL OF INORGANIC BIOCHEMISTRY
(2021)
Article
Chemistry, Physical
Zhi Zhou, Gerard Roelfes
Summary: The article describes a tandem Michael addition/enantioselective protonation reaction catalyzed by an artificial enzyme in water. Through the use of abiological catalytic sites and a Lewis acid Cu(II) complex, high stereocontrol was achieved. This illustrates the potential of exploiting synergistic catalysis in artificial enzymes for challenging reactions.
Article
Chemistry, Physical
Reuben B. Leveson-Gower, Zhi Zhou, Ivana Drienovska, Gerard Roelfes
Summary: Incorporating noncanonical amino acid para-aminophenylalanine into a nonenzymatic protein scaffold creates a proficient and stereoselective artificial enzyme for specific reactions. Analysis of evolved mutants reveals different catalytic activities and reaction pathways.
Article
Chemistry, Physical
Reuben B. Leveson-Gower, Ruben M. de Boer, Gerard Roelfes
Summary: The incorporation of organocatalysts into protein scaffolds offers a solution for overcoming limitations in catalysis. This study demonstrates the successful incorporation of para-aminophenylalanine into a non-enzymatic protein scaffold, resulting in a proficient and enantioselective artificial enzyme for the Friedel-Crafts alkylation reaction.
Review
Chemistry, Physical
Reuben B. Leveson-Gower, Gerard Roelfes
Summary: Friedel-Crafts alkylation and acylation reactions are important in synthetic and industrial chemistry. Researchers have expanded the application of these reactions through directed evolution and created bio-hybrid catalysts. This review summarizes these efforts and discusses future routes for more efficient and benign Friedel-Crafts reactions.
Article
Chemistry, Multidisciplinary
Linda Ofori Atta, Zhi Zhou, Gerard Roelfes
Summary: This study reports an artificial-enzyme-catalysed biocatalytic cascade that promotes reactions that have no equivalent in nature. By conducting in vivo biocatalytic cascades inside E. coli cells, this research takes an important step towards achieving a hybrid metabolism.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Ruben Maaskant, Ehider A. Polanco, Roos C. W. van Lier, Gerard Roelfes
ORGANIC & BIOMOLECULAR CHEMISTRY
(2020)
Article
Chemistry, Physical
Sara H. Mejias, Gerard Roelfes, Wesley R. Browne
PHYSICAL CHEMISTRY CHEMICAL PHYSICS
(2020)
