Article
Chemistry, Multidisciplinary
Matt Timmers, Wouter Peeters, Niels J. Hauwert, Cristianne J. F. Rijcken, Tina Vermonden, Ingrid Dijkgraaf, Rob M. J. Liskamp
Summary: This article describes the site-specific attachment of the reactive TMTHSI-click handle to the N-terminus of peptides and proteins. The resulting molecular constructs can be used in strain-promoted azide alkyne cycloaddition (SPAAC) for reaction with azide-containing proteins. The article also discusses the N-terminal specific attachment of the reactive TMTHSI-click handle to peptides and proteins, followed by strain-promoted cycloaddition with azide-containing compounds.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Multidisciplinary
Samuel Fura, Samuel Abidemi Oluwole, Queen Assala Hakim, Hikari Sanchez, Daniela Toledo, Aline Andrea Quintana, Christian Agatemor
Summary: Chemists have always emphasized cross-disciplinary approaches to solve human problems. We designed a laboratory experiment to integrate chemistry with biology, which helps undergraduate and graduate students appreciate the importance of interdisciplinarity. The experiment introduces classical and emerging techniques used in chemistry and molecular biology research and allows students to apply organic chemistry, bioanalytical chemistry, and molecular biology concepts while learning essential techniques in drug discovery, chemical toxicology, chemical biology, and molecular biology. This experiment prepares and motivates students to pursue research at the interface of chemistry and biology.
JOURNAL OF CHEMICAL EDUCATION
(2023)
Review
Chemistry, Multidisciplinary
Tingxizi Liang, Zhaowei Chen, Hongjun Li, Zhen Gu
Summary: Bioorthogonal chemistry has made substantial progress in the past few decades and has been widely applied in biomedical practices. This article reviews the development and recent advances of bioorthogonal chemistry, with a focus on the biomedical application of bioorthogonal catalysis.
TRENDS IN CHEMISTRY
(2022)
Review
Chemistry, Multidisciplinary
Yiming Liao, Baoqi Wu, Rongzhi Tang, Feng Lin, Yu Tan
Summary: This article reviews the wide application and advantages of SPAAC reaction in fields such as biomedicine and materials science. The stability and reactivity of cycloalkynes, as well as their reaction rate constants in SPAAC, are discussed. The research progress in the preparation methods of commonly used cyclic alkynes is introduced. Furthermore, the application, challenge, and future outlook of SPAAC without copper catalysis are discussed and prospected.
PROGRESS IN CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Borja Cirera, Alexander Riss, Pingo Mutombo, Jose Urgel, Jose Santos, Marco Di Giovannantonio, Roland Widmer, Samuel Stolz, Qiang Sun, Max Bommert, Roman Fasel, Pavel Jelinek, Willi Auwarter, Nazario Martin, David Ecija
Summary: The design of organometallic complexes is crucial in modern organic chemistry and catalysis. On-surface synthesis has recently emerged as a disruptive method to design compounds and nanomaterials previously considered impossible. The activation of inner diacetylene moieties of a molecular precursor by copper surface adatoms has led to the formation of unprecedented organocopper metallacycles on Cu(111), paving the way for new avenues in organometallic compound engineering and polyyne chemistry on surfaces.
Correction
Chemistry, Inorganic & Nuclear
Firdaus Rahaman Gayen, Abdul Aziz Ali, Debashree Bora, Saptarshi Roy, Supriya Saha, Lakshi Saikia, Rajib Lochan Goswamee, Biswajit Saha
Summary: This study focuses on the synthesis and characterization of a ferrocene functionalized Schiff base containing Cu(II) complex, and demonstrates its catalytic activity in the azide alkyne cycloaddition reaction at parts-per-million levels.
DALTON TRANSACTIONS
(2021)
Article
Polymer Science
Eric Meichsner, Darryl Fong, Dialia E. M. Ritaine, Alex Adronov
Summary: The study demonstrates the use of SPAAC as a polymerization tool to rapidly prepare a polymer library with diverse thermal and stimulus-responsive properties. The polymerization process does not require heating or catalyst addition, enabling the preservation of sensitive moieties and demonstrating solid- and solution-state stimulus-responsiveness.
JOURNAL OF POLYMER SCIENCE
(2021)
Article
Biochemistry & Molecular Biology
Beatriz Lozano-Torres, Juan F. Blandez, Alba Garcia-Fernandez, Felix Sancenon, Ramon Martinez-Manez
Summary: This study describes a new method for senescent cell detection based on lipofuscin labeling using a biorthogonal reaction. The method involves a two-step reaction that forms a clear fluorescence pattern in senescent cells, providing an alternative tool for senescent cell detection.
Article
Chemistry, Organic
Linwei Zeng, Fengzhi Zhang, Sunliang Cui
Summary: A modular and practical click chemistry is developed for the atroposelective synthesis of 1-triazolyl-2-naphthylamines. This method involves a [3 + 2] cycloaddition reaction under Rh-catalysis to assemble various aromatic or aliphatic azides with 1-alkynyl-2-naphthylamines, resulting in valuable 1-triazolyl-2-naphthylamine scaffolds. This asymmetric click technology offers easily accessible starting materials, mild reaction conditions, facile scalability, and good enantioselectivity. The thermostability of the products highlights their great potential for applications, while the synthetic transformations further enhance the molecular diversity of atropisomers.
Article
Chemistry, Organic
Robby Vroemans, Sergio R. Ribone, Joice Thomas, Luc Van Meervelt, Thierry Ollevier, Wim Dehaen
Summary: A new method for preparing novel homochiral atropisomeric sulfanyl- and sulfoxide-substituted naphthyltriazoles is described in this study, providing a new pathway for stable 1,2,3-triazole-based atropisomers. Sixteen sulfanyl-substituted naphthyltriazoles were obtained via triazolization reaction, followed by monooxidation. The absolute configuration of the substituted naphthyltriazoles was determined using X-ray crystallography and confirmed with computational DFT calculations.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Review
Chemistry, Physical
Chang-Qing Qin, Cheng Zhao, Guo-Shu Chen, Yun-Lin Liu
Summary: Catalytic enantioselective azide-alkyne cycloaddition (E-AAC) is an efficient technology for constructing diverse chiral triazoles, with applications in synthetic and medicinal chemistry, biological chemistry, and materials science. Significant developments have been made in copper-, nickel-, iridium-, and rhodium-catalyzed E-AAC reactions in the past six years. This review summarizes these advancements according to different strategies implemented.
Article
Chemistry, Inorganic & Nuclear
Yu-Hsuan Shen, Alec M. Esper, Ion Ghiviriga, Khalil A. Abboud, Kirk S. Schanze, Christian Ehm, Adam S. Veige
Summary: Combining strain-promoted azide-alkyne cycloaddition (SPAAC) and inorganic click (iClick) reactivity allows access to metal 1,2,3-triazolates. Experimental and computational insights reveal that the iClick reactivity of metal azides depends on the accessibility of the azide functionality rather than electronic effects. Sterically unencumbered azide functionalities exhibit SPAAC iClick reactivity with cyclooctyne.
DALTON TRANSACTIONS
(2021)
Review
Chemistry, Multidisciplinary
Markus Kufleitner, Lisa Maria Haiber, Valentin Wittmann
Summary: Glycans play important roles in biological recognition events. A method called metabolic glycoengineering (MGE) has been developed to visualize or isolate glycans. This approach involves treating cells or organisms with modified carbohydrate derivatives, which are then metabolized and incorporated into newly synthesized glycoconjugates. MGE has also been used to target drugs, nanoparticles, or cells to specific locations.
CHEMICAL SOCIETY REVIEWS
(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)
Review
Chemistry, Multidisciplinary
Tyler K. Heiss, Robert S. Dorn, Jennifer A. Prescher
Summary: Bioorthogonal phosphines were introduced in the context of the Staudinger ligation and have since been widely used to tag azide-functionalized biomolecules in biological experiments. Recent advances in this field have highlighted the versatility and importance of bioorthogonal phosphines in various biological pursuits.
Article
Chemistry, Multidisciplinary
Wilson Luo, Pierangelo Gobbo, Christopher D. McNitt, Dewey A. Sutton, Vladimir V. Popik, Mark S. Workentin
CHEMISTRY-A EUROPEAN JOURNAL
(2017)
Article
Neurosciences
Maxime J. Parent, Eduardo R. Zimmer, Monica Shin, Min Su Kang, Vladimir S. Fonov, Axel Mathieu, Antonio Aliaga, Alexey Kostikov, Sonia Do Carmo, Doris Dea, Judes Poirier, Jean-Paul Soucy, Serge Gauthier, A. Claudio Cuello, Pedro Rosa-Neto
JOURNAL OF NEUROSCIENCE
(2017)
Article
Chemistry, Multidisciplinary
Mengzhe Wang, Christopher D. McNitt, Hui Wang, Xiaofen Ma, Sarah M. Scarry, Zhanhong Wu, Vladimir V. Popik, Zibo Li
CHEMICAL COMMUNICATIONS
(2018)
Article
Biochemical Research Methods
Robert Hopewell, Karen Ross, Alexey Kostikov, Tharick A. Pascoal, Thais Alberti, Monica Lacatus-Samoila, Jean-Paul Soucy, Idriss Bennacef, Eliane Kobayashi, Min Su Kang, Pedro Rosa-Neto, Gassan Massarweh
JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS
(2019)
Article
Biochemical Research Methods
Hussein Bdair, I-Huang Tsai, Kelly Smart, Chawki Benkelfat, Marco Leyton, Alexey Kostikov
JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS
(2019)
Article
Chemistry, Multidisciplinary
Marcel Dommaschk, Javier Echavarren, David A. Leigh, Vanesa Marcos, Thomas A. Singleton
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2019)
Article
Multidisciplinary Sciences
Thomas A. Singleton, Mehdi Boudjemeline, Robert Hopewell, Dean Jolly, Hussein Bdair, Alexey P. Kostikov
JOVE-JOURNAL OF VISUALIZED EXPERIMENTS
(2019)
Article
Biochemical Research Methods
Thomas A. Singleton, Hussein Bdair, Justin J. Bailey, Sangho Choi, Arturo Aliaga, Pedro Rosa-Neto, Ralf Schirrmacher, Vadim Bernard-Gauthier, Alexey Kostikov
JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS
(2020)
Article
Biochemistry & Molecular Biology
Hussein Bdair, Thomas A. Singleton, Karen Ross, Dean Jolly, Min Su Kang, Arturo Aliaga, Marius Tuznik, Tanpreet Kaur, Said Yous, Jean-Paul Soucy, Gassan Massarweh, Peter J. H. Scott, Robert Koeppe, Gilberto Spadoni, Annalida Bedini, David A. Rudko, Gabriella Gobbi, Chawki Benkelfat, Pedro Rosa-Neto, Allen F. Brooks, Alexey Kostikov
Summary: This study aimed to develop selective radiotracers for PET imaging of melatonin receptors. Four radiotracers were synthesized and evaluated, but their failure was attributed to rapid metabolism in liver microsomes. Nevertheless, PET imaging proved valuable for investigating the brain permeability of new therapeutic compounds targeting the melatonergic system.
ACS CHEMICAL NEUROSCIENCE
(2022)
Meeting Abstract
Endocrinology & Metabolism
Alexey Kostikov, Thomas A. Singleton, Hussein Bdair, Karen Ross, Min-Su Kang, Arturo Aliaga, Tanpreet Kaur, Allen F. Brooks, Peter J. H. Scott, Gabriella Gobbi, Chawki Benkelfat, Marco Leyton, Said Yous, Jean-Paul Soucy, Pedro Rosa-Neto
JOURNAL OF CEREBRAL BLOOD FLOW AND METABOLISM
(2021)
Article
Biochemical Research Methods
Matthew Bjerknes, Hazel Cheng, Christopher D. McNitt, Vladimir V. Popik
BIOCONJUGATE CHEMISTRY
(2017)
Article
Chemistry, Organic
Faiza Diaba, Gisela Trenchs
Summary: The first violet light-mediated synthesis of gamma- and delta-lactams from N-alkenyl trichloroacetamides is reported in this paper. The reactions are conducted in tetrahydrofuran or 2-methyltetrahydrofuran as the sole solvent without catalysts or additives, under non-anhydrous conditions in an air atmosphere where the solvent serves as the radical initiator.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Feroze Hussain, Sajjad Ahmed, Ashiq Hussain Padder, Qazi Naveed Ahmed
Summary: This study reports a novel and efficient one-pot synthesis method for mixed phosphorotrithioates, which does not require supplementary additives and shows broad applicability.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Hyunjin Oh, Ikyon Kim
Summary: A new 1,2,4-triazole-pyrrolo[1,2-a]pyrazine hybrid system, 6-acylpyrrolo[1,2-a][1,2,4]triazolo[5,1-c]pyrazine, was synthesized using a catalyst-free method. This method involved sequential exposure of pyrrole-2-carbonitrile-derived substrates to DMF-DMA and acyl hydrazide, resulting in the formation of acylated pyrazine and 1,2,4-triazole rings, enabling the installation of various substituents at specific positions on the core skeleton.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Ming Yan, Si-fan Wang, Yong-po Zhang, Jin-zhong Zhao, Zhuo Tang, Guang-xun Li
Summary: Here we developed an efficient photocatalytic approach for the convenient preparation of sulfinamides. The reaction allows for the gram-scale preparation of sulfinamides and the one-pot synthesis of various sulfonyl amides.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Farzaneh Bandehali-Naeini, Zahra Tanbakouchian, Noushin Farajinia-Lehi, Nicolas Mayer, Morteza Shiri, Martin Breugst
Summary: Two tandem catalytic systems were developed for the synthesis of novel 3,4-disubstituted maleimides using the same Ugi adducts. Different maleimide structures can be synthesized using either Pd or Cu catalysis.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Tanya Raghava, Anjan Chattopadhyay, Subhadeep Banerjee, Nivedita Sarkar
Summary: Amine substitution of two ortho fluorine atoms of tetrafluoroterephthalonitrile through SNAr chemistry is easily achievable. But further fluorine substitution is only possible under forcing conditions, yielding valuable fluorophores for bioimaging.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Review
Chemistry, Organic
Anju Chadha, Santosh Kumar Padhi, Selvaraj Stella, Sowmyalakshmi Venkataraman, Thangavelu Saravanan
Summary: Alcohol dehydrogenases are enzymes that use cofactors for oxidation or reduction reactions of alcohols or carbonyl compounds. They are utilized in green chemistry and have applications in the production of pharmaceuticals. Recombinant enzymes have solved the challenge of producing purified enzymes in large quantities. Engineered alcohol dehydrogenases have been used in asymmetric synthesis in industry. Various methods have been established for regenerating expensive cofactors to make the enzymatic process more efficient and economically viable.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
