Article
Chemistry, Multidisciplinary
Mariama Djalo, Maria J. S. A. Silva, Helio Faustino, Sandra N. Pinto, Ricardo Mendonca, Pedro M. P. Gois
Summary: The ability to selectively append multiple functionalities on a native peptide backbone is a complex and high-demanding tool in modern chemical biology. This study presents the design of novel NHS-activated acrylates that can hold various payloads in a single bioconjugation handle, allowing for site-selective and orthogonal targeting of the N-terminal cysteine of peptides.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Multidisciplinary
Dattatraya Gautam Rawale, Kalyani Thakur, Pranav Sreekumar, T. K. Sajeev, A. Ramesh, Srinivasa Rao Adusumalli, Ram Kumar Mishra, Vishal Rai
Summary: In this study, a linchpin is found to create a unique chemical space, enabling site-selectivity for histidine and aspartic acid modifications, overcoming the limitations of chemoselectivity.
Review
Chemistry, Organic
Alicia Boto, Concepcion C. Gonzalez, Dacil Hernandez, Ivan Romero-Estudillo, Carlos J. Saavedra
Summary: The site-selective modification of peptide backbones allows for precise adjustment of peptide conformation, folding ability, and physico-chemical properties, and recent years have seen significant advancements in this area. Modifications not only at internal backbone positions, but also at N- and C-termini are widely discussed. Through chemical methodologies and enzyme-catalyzed reactions, unprecedented regio- and stereoselectivity in backbone modifications have been achieved.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Physical
Martin D. Witte, Adriaan J. Minnaard
Summary: Oligosaccharides, either on their own or as part of other compounds, are widely present in nature and play important roles in biology, medicine, and materials science. Modifying their structure and introducing reactive and reporter groups is crucial for studying their function. Recent progress has been made in developing selective and late-stage modification methods for oligosaccharides, particularly in catalysis research.
Article
Chemistry, Analytical
Fei Chen, Yuanqiang Hao, Xiangfei Zhang, Meiling Shao, Guangxiu Cao, Bin Zhai, Chi Zhang
Summary: SDBCPs have unique photophysical and self-assembly properties, but their potential for sensing applications has been rarely explored. The novel SDBCP P3EPT(17)-b-P3ImHT(33) can self-assemble into nanofibers in DMSO and quasispherical micelles in water, and it has been utilized as a fluorescent nanoprobe for the selective and sensitive detection of Cu2+ with a detection limit as low as 0.13 nM. Moreover, fluorescence imaging studies have shown that PT-CPNs can effectively detect Cu2+ in living HeLa cells.
SENSORS AND ACTUATORS B-CHEMICAL
(2021)
Article
Chemistry, Multidisciplinary
Yuanyuan Ping, Qi Pan, Ya Guo, Yongli Liu, Xiao Li, Minyan Wang, Wangqing Kong
Summary: Switchable selectivity in skeletal rearrangement can be achieved by controlling the migratory aptitude of different groups. Modifying the ligands on the metal catalyst and changing the oxidation states of the metal allow control over the migratory ability. This method enables site-selective activation and reorganization of C-C bonds and has been used for the synthesis of fluorine-containing scaffolds with medicinal relevance.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Multidisciplinary
Lei Wang, Todd L. Lowary
Summary: This article describes the synthesis of two lipid-linked polysaccharides related to LPS O-chain biosynthesis in Escherichia coli O9a, providing insights into the challenges of chemically synthesizing structurally-defined polysaccharides.
Article
Chemistry, Multidisciplinary
Jake H. H. Schwab, Jake B. B. Bailey, Milan Gembicky, Julia M. M. Stauber
Summary: Multivalency is important in nature for strong and reversible interactions, and its design in synthetic assemblies is of interest to chemists for understanding biological recognition and creating chemical tools. This study presents a systematic and modular approach to design molecular multivalent protein-binding constructs, allowing for control over size, morphology, and valency. The assemblies showed strong multivalent binding to the model lectin Concanavalin A, with the strength of binding depending on the number of saccharide units present.
Review
Chemistry, Multidisciplinary
Muhammed Haque, Nafsika Forte, James R. Baker
Summary: Selective modification of lysine residues presents a significant challenge due to their popularity in bioconjugation. Antibody-drug conjugates heavily rely on lysine bioconjugation for synthesis, highlighting the importance of achieving site-selective lysine modification methodologies.
CHEMICAL COMMUNICATIONS
(2021)
Review
Chemistry, Multidisciplinary
Lujuan Xu, Seah Ling Kuan, Tanja Weil
Summary: Site-selective protein functionalization is a valuable tool for studying protein structures and functions in complex cellular environments and developing semi-synthetic protein conjugates. Dual functionalization allows the incorporation of two different types of functionalities at distinct locations, expanding the features of native proteins. The combination of various molecules offers new avenues for designing precision protein therapeutics with synergistic/addeitive properties.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Jian Li, Qi-Long Hu, Zhendong Song, Albert S. C. Chan, Xiao-Feng Xiong
Summary: Site-selective modification of peptides/proteins is a crucial method for studying post-translational modifications, chemical biology, and drug development. In this study, a visible-light-driven and Cys-directed Lys site-selective stapling approach was developed, enabling selective modification and multi-functionalization.
SCIENCE CHINA-CHEMISTRY
(2022)
Article
Biochemistry & Molecular Biology
Richard C. Brewster, Alison N. Hulme
Summary: Post-translational modifications (PTMs) play a crucial role in controlling protein structure and function in organisms, but their study is complicated due to difficulties in selectively introducing PTMs onto proteins. Designing reagents that accurately mimic PTMs and selectively modify specific amino acid residues in proteins is a challenging task.
Article
Chemistry, Multidisciplinary
Ruben W. Kolkman, Loes Segerink, Jurriaan Huskens
Summary: By organizing multiple MBDs on a surface, a multivalent binding platform can significantly improve the preselection of hypermethylated DNA from liquid biopsy samples. The selectivity for methylated over non-methylated DNA can be optimized by carefully tuning the MBD density. Implementing such an enrichment step in an analytical process or a lab-on-a-chip device holds strong applicability in a medical setting.
ADVANCED MATERIALS INTERFACES
(2022)
Article
Chemistry, Organic
Arunachalam Kesavan, Akshaya Kumar Sahu, Pazhamalai Anbarasan
Summary: An efficient method for the acid-catalyzed carbosulfenylation of 1,6-diene has been developed using N-(aryl/alkylthio)succinimides as a thiolating reagent. This reaction involves the generation of an episulfonium ion followed by intramolecular trapping with alkenes, resulting in good yields of diverse thiolated dehydropiperidines. In addition, the synthesis of dihydropyran and cyclohexene derivatives, as well as the conversion of the arylthiol moiety to useful functional groups, was also demonstrated.
Article
Chemistry, Multidisciplinary
Alexandra Ramsey, Amanda J. Bischoff, Matthew B. Francis
Summary: This study introduces a new enzymatic method for constructing protein- and DNA-AuNP conjugates, presenting highly stable AuNPs that can be selectively activated with an enzyme and offer the ability to conjugate proteins or DNA through a diverse set of functional handles. The enzymatic oxidative coupling on AuNPs was applied successfully to the construction of tobacco mosaic virus (TMV)-AuNP conjugates, demonstrating energy transfer between the AuNPs and fluorophores on TMV.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Organic
Marc-Andre Kasper, Lukas Lassak, Annette M. Vogl, Isabelle Mai, Jonas Helma, Dominik Schumacher, Christian P. R. Hackenberger
Summary: Bis-ethynylphosphonamidates allow for a simple chemoselective addition of two thiol-containing modules in a row. Functional O-substituents with tunable hydrophilicity enable further subsequent conjugations, facilitating the construction of protein-protein conjugates. The increased spacer length between the ethynylphosphonamidates simplifies the formation of a conjugate from bulky proteins.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Biochemistry & Molecular Biology
Carolina Sarto, Sebastian Florez-Rueda, Mehrnoosh Arrar, Christian P. R. Hackenberger, Daniel Lauster, Santiago Di Lella
Summary: This study determined the binding affinity between ACE2-derived peptides and the RBD of SARS-CoV-2, and identified critical peptide anchors. New ACE2-derived peptides were developed based on interface analysis, and a correlation between helicity and binding affinity was found. Additionally, a cyclized version of p6 with increased helicity and reduced K (D) value was created.
BIOLOGICAL CHEMISTRY
(2022)
Article
Biochemical Research Methods
Lutz Adam, Eva Muller, Kai Ludwig, Simon Klenk, Daniel Lauster, Susanne Liese, Andreas Herrmann, Christian P. R. Hackenberger
Summary: The conjugation of virus-binding ligands to multivalent carriers is an effective strategy to inhibit viral entry into host cells. Even partially sialylated ligands can retain their inhibitory effect, and carriers carrying two different ligand-linker structures showed higher viral inhibition.
BIOCONJUGATE CHEMISTRY
(2022)
Article
Biochemistry & Molecular Biology
Pascal M. Engelhardt, Sebastian Florez-Rueda, Marco Drexelius, Joerg-Martin Neudoerfl, Daniel Lauster, Christian P. R. Hackenberger, Ronald Kuehne, Ines Neundorf, Hans-Guenther Schmalz
Summary: Researchers used a rigidified diproline-derived module ProM-5 to induce alpha helicity in ACE2-inspired peptide sequences. They found increased alpha helicity when non-binding amino acids were replaced with alanine. The binding affinities of the peptides towards the spike protein showed that the alpha-helical content had only a subtle influence, with one specific peptide displaying a strong binding affinity.
Article
Multidisciplinary Sciences
Huan Sun, Haiyang Jia, Olivia Kendall, Jovan Dragelj, Vladimir Kubyshkin, Tobias Baumann, Maria-Andrea Mroginski, Petra Schwille, Nediljko Budisa
Summary: In this study, the authors investigated the halogenation of the prokaryotic cell division protein FtsZ and demonstrated its effects on protein structure and dynamics. They provided valuable insights into the mechanism of halogen influence through experiments and theories.
NATURE COMMUNICATIONS
(2022)
Article
Biochemistry & Molecular Biology
Dusica Maysinger, Issan Zhang, Pei You Wu, Marten Kagelmacher, Haiming Daniel Luo, Jayachandran N. Kizhakkedathu, Jens Dernedde, Matthias Ballauf, Rainer Haag, Adeola Shobo, Gerhard Multhaup, R. Anne McKinney
Summary: The objective of this study was to investigate the interaction between polyglycerols with sulfate or sialic acid functional groups and high mobility group box 1 (HMGB1). The study aimed to determine if polyglycerols could prevent the loss of morphological plasticity in excitatory neurons in the hippocampus. The results suggest that dendritic and linear polyglycerols can interact with HMGB1 and prevent dendritic spine loss in excitatory neurons.
ACS CHEMICAL NEUROSCIENCE
(2023)
Review
Chemistry, Multidisciplinary
Eleftheria Poulou, Christian P. R. Hackenberger
Summary: This review highlights the groundbreaking discoveries and applications of Staudinger reactions in the molecular life sciences, including its engineering as a bioorthogonal reaction and its recent applications in generating next-generation biopharmaceuticals through modern bioconjugation methods.
ISRAEL JOURNAL OF CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Raju Bej, Chuanxiong Nie, Kai Ludwig, Vahid Ahmadi, Jakob Trimpert, Julia M. Adler, Tatyana L. Povolotsky, Katharina Achazi, Marten Kagelmacher, Ricardo Martin Vidal, Jens Dernedde, Benedikt B. Kaufer, Rainer Haag
Summary: Researchers have developed a synthetic nanostructure that mimics the properties of mucins, the key component of protective mucus barrier. This mucin-inspired fiber showed strong activity against SARS-CoV-2 and its mutant strain, with a low inhibitory concentration. The study also investigated the impact of fiber length on the inhibition of SARS-CoV-2.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Don S. Munasinghe, Marc-Andre Kasper, Radomir Jasinski, Karolina Kula, Marcin Palusiak, Malgorzata Celeda, Grzegorz Mloston, Christian P. R. Hackenberger
Summary: By utilizing the reactivity of ethynyl-phosphonites, novel P(V)-containing five-membered heterocycles were synthesized via (3+2)-cyclization reactions with aldehydes or cycloaliphatic thioketones, yielding satisfactory to excellent yields. The reactions with thioketones proceeded smoothly at room temperature without any catalyst, while the conversions with aldehydes required the addition of triethylamine as a base. A step-wise (3+2)-cyclization mechanism for the formation of the 1,3-thiaphosphole ring was proposed based on DFT quantum chemical calculations. This study introduces new cyclization reactions using unsaturated phosphonites as central synthetic building blocks to access stable phosphorus-containing heterocycles with unexplored potential in the molecular sciences.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Biochemistry & Molecular Biology
Nisha Mohanan, Michael C. -H. Wong, Nediljko Budisa, David B. Levin
Summary: In this study, genes encoding an intracellular lipase (LIP3), an extracellular lipase (LIP4), and an intracellular PHA depolymerase (PhaZ) were identified in Pseudomonas chlororaphis PA23. These genes were cloned and expressed in Escherichia coli, and the biochemical and substrate preferences of the enzymes were characterized. The results showed that these enzymes exhibited different properties, but they demonstrated broad substrate specificity and could hydrolyze various polymers, including PHAs, pNP alkanoates, and PLA. Furthermore, the enzymes were able to degrade both biodegradable and synthetic polymers, such as PCL and PES, as evidenced by GPC analyses.
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2023)
Article
Pharmacology & Pharmacy
Hanna Koeppe, Daniel Horn, Johanna Scholz, Elisa Quaas, Sebastian Schoetz, Felix Reisbeck, Katharina Achazi, Ehsan Mohammadifar, Jens Dernedde, Rainer Haag
Summary: Induced angiogenesis is a key factor in tumor progression and can be targeted by sunitinib. However, sunitinib suffers from low bioavailability and a short half-life. In this study, dendritic polyglycerol (dPG) with a sheddable shell was developed as a drug delivery system to overcome these limitations.
INTERNATIONAL JOURNAL OF PHARMACEUTICS
(2023)
Article
Biochemistry & Molecular Biology
Georg Johannes von Freiherr Sass, Matthew Blain-Hartung, Tobias Baumann, Katrina T. Forest, Peter Hildebrandt, Nediljko Budisa
Summary: Orthogonal translation is an efficient tool for parameterization of structural and dynamic phenomena in proteins. Nitrile-containing tryptophan analogs are useful probes for studying local electrostatics and hydrogen bonding. This study reports the engineering of a tyrosyl-tRNA synthetase variant capable of incorporating 5-cyanotryptophan via orthogonal translation, and demonstrates its utility by inserting it into a photosensor protein.
Review
Biochemistry & Molecular Biology
Peter Goettig, Nikolaj G. Koch, Nediljko Budisa
Summary: Amino acids play crucial roles in organisms, being encoded by genetic code and modified post-translationally to generate various functional amino acids. These non-canonical amino acids are important for protein stability and function, and have wide applications in drug development and biological research.
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2023)
Article
Chemistry, Multidisciplinary
Jan Vincent V. Arafiles, Jonathan Franke, Luise Franz, Jacobo Gomez-Gonzalez, Kristin Kemnitz-Hassanin, Christian P. R. Hackenberger
Summary: This study presents a powerful and efficient strategy for the intracellular delivery of functional cargoes. By increasing the retention on the cellular membrane, the authors found that CPP additives with a hydrophobic peptide sequence can enhance the uptake of protein cargoes without causing cytotoxicity. The results provide important design principles for cell-surface-retained CPP additives and demonstrate the potential of hydrophobic CPP additives in delivering fluorescent proteins and functional macrocyclic peptides.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Multidisciplinary
Jacob Gorenflos L. Lopez, Peter Schmieder, Kristin Kemnitz-Hassanin, Hatice Ceyda Asikoglu, Arif Celik, Christian E. Stieger, Dorothea Fiedler, Stephan Hinderlich, Christian P. R. Hackenberger
Summary: This study introduces a real-time assay to monitor different enzymatic steps of sialic acid biosynthesis. The NMR techniques used in this study allow for the identification of characteristic signals and suggest that MNK phosphorylation reaction is exclusive for N-acetylmannosamine generated by GNE. Competition experiments reveal the preference of an N-acetylglucosamine-preferring kinase in the phosphorylation process.
Review
Chemistry, Multidisciplinary
Dan He, Yawen Li, Fuwen Zhao, Yuze Lin
Summary: High trap density in organic solar cells leads to localized charge carriers and reduced carrier lifetime, limiting device efficiency. This feature article summarizes the recent advances of trap suppression by material design and device engineering.
CHEMICAL COMMUNICATIONS
(2024)
Review
Chemistry, Multidisciplinary
Olivier Monfort, Arshitha Madhusudhan, Martin Motola
Summary: This article presents the advantages of coupling photocatalysis and Fenton-based processes for environmental remediation and discusses their synergy. It critically examines the simultaneous triggering of these two processes and provides insights into research approaches. The study aims to enhance understanding of this complex process and highlight the potential integration of new catalysts in current wastewater treatment technology.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Manideepa Dhar, Chittaranjan Mishra, Avijit Das, Uttam Manna
Summary: An approach of 'polymerization of monomers in its aggregated form' has been introduced to tailor the water wettability of fibrous and porous substrates, achieving hydrophobicity to superhydrophobicity transition, as well as patterned wettability. This facile chemical method provides a durable coating with adjustable and patterned wettability for various potential applications.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Saswat Ranjan Bhoi, Chhanda Debnath, Shikha Gandhi
Summary: In this article, a novel catalytic reaction using Pd(0) and Bronsted acid is reported for the synthesis of biologically important imidazolidinone-fused N-heterocycles through redox-neutral intramolecular N-allylation of indoles and pyrroles with alkynes. This atom-economical method is applicable to a wide range of substrates and eliminates the need for leaving groups or oxidizing agents commonly used in traditional allylation reactions.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Longkun Chen, Mingshuai Zhang, Meichen Liu, Zhuoyuan Liu, Yuetong Qiu, Zhilai Zhang, Fuchao Yu, Jiuzhong Huang
Summary: In this study, an efficient Rh(III)-catalyzed selective mono- and dual-C-H bond functionalization/cyclization with iodonium ylide as the sole coupling partner was demonstrated. Fused benzodiazepine skeletons were obtained in excellent yields, providing an improved approach to dual C-H unsymmetrical functionalization.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Alice Kennett, Sven Epple, Gabriella van der Valk, Irene Georgiou, Evelyne Gout, Romain R. Vives, Angela J. Russell
Summary: This study presents the design and synthesis of sulfated disaccharide inhibitors based on IdoA(2S)-GlcNS(6S), which showed potent inhibition of Sulf-2. The results suggest that IdoA(2S)-GlcNS(6S) is the shortest fragment size required for effective inhibition of Sulfs, and a trisulfated disaccharide is identified as the minimal fragment size of heparan sulfate for effective endosulfatase inhibition.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Mauro Garbini, Andrea Brunetti, Riccardo Pedrazzani, Magda Monari, Massimo Marcaccio, Giulio Bertuzzi, Marco Bandini
Summary: The self-adaptability of galvanostatic electrolysis was found to be helpful in a multistage chemo- and diastereoselective electrochemically promoted cyclodimerization of chalcones. Through a series of reductive events, densely functionalized cyclopentanes with five contiguous stereocenters were obtained (25 examples, yields up to 95%, dr values up to >20:1). Further experimental and electrochemical investigations indicated the crucial role of dynamic kinetic resolution of the aldol intermediate in the reaction mechanism.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Dhananjay S. Nipate, Neha Meena, Prakash N. Swami, Krishnan Rangan, Anil Kumar
Summary: In this study, the synthesis of functionalized benzo[a]phenazines and indazolo[2,3-a]quinolines was achieved through Rh(III)-catalyzed oxidative annulation of 2-arylquinoxalines and 2-aryl-2H-indazoles with allyl alcohols. The method showed a wide substrate scope, excellent functional group tolerance, good to high yields of annulated products, and the capability for scaled-up synthesis. A tentative mechanism of the annulation reaction was proposed based on a preliminary mechanistic investigation.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Ruonan Zhang, Abudukadi Tudi, Xia Yang, Xuping Wang, Zhihua Yang, Shujuan Han, Shilie Pan
Summary: A new lead tellurium borate material with a unique fundamental building block [B4O10] was synthesized and found to exhibit high birefringence. The structure-property relationship was discussed using first-principles calculations.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Amresh Kumar Singh, Baishali Thakurta, Anupam Giri, Monalisa Pal
Summary: This study introduces three key concepts for the quick synthesis of large-scale high-quality 2D materials films and their utilization in device fabrication.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Reina Hagiwara, Shun Nishimura, Kosuke Okeyoshi
Summary: A copolymer-conjugated nanocatalytic system has been developed to improve electron transfer and enhance photoinduced H2 generation.
CHEMICAL COMMUNICATIONS
(2024)
