Article
Polymer Science
Aaron Priester, Jimmy Yeng, Krista Hilmas, Anthony J. Convertine
Summary: Polysorbate 80 (PS80) was reacted with 3-mercaptopropyl trimethoxysilane (SiSH) via a photoinitiated thiol-ene reaction to obtain thiol-functional nanoparticles. These nanoparticles have a high number of thiol residues per particle, allowing for easy modification of particle properties. When added to 3D printing resin, the thiol-functional nanoparticles significantly enhance the curing rate.
Article
Chemistry, Multidisciplinary
Koki Nakatsu, Akimitsu Okamoto, Gosuke Hayashi, Hiroshi Murakami
Summary: This article reports a novel one-pot multi-segments ligation strategy using a specific formaldehyde scavenger to efficiently synthesize proteins by changing the pH values. By this method, mono-ubiquitinated histone H2A.Z was successfully synthesized.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Biochemistry & Molecular Biology
Sae Suzuki, Yuya Nakajima, Naoki Kamo, Akihisa Osakabe, Akimitsu Okamoto, Gosuke Hayashi, Hiroshi Murakami
Summary: This paper reports the use of thiocholine as a thiol catalyst in chemical protein synthesis. Thiocholine was found to be useful for NCL-based peptide ligation and metal-free desulfurization, with comparable efficiency to other alkyl thioesters. Importantly, thiocholine showed better reactivity as a thiol additive in desulfurization. The successful synthesis of two differently methylated histone H3 proteins was achieved via one-pot NCL and desulfurization with thiocholine.
Article
Chemistry, Multidisciplinary
Lucas Kambanis, Timothy S. Chisholm, Sameer S. Kulkarni, Richard J. Payne
Summary: This study introduces an iterative one-pot peptide ligation strategy that combines the rapid diselenide-selenoester ligation reaction with photodeselenisation chemistry, enabling the efficient synthesis of protein fragments in a short period of time. The use of a novel photolabile protecting group for selenocysteine side chains allows for mild, reagent-free deprotection using visible light, facilitating subsequent ligation reactions without the need for purification.
Article
Multidisciplinary Sciences
Yuwen Wang, Patrick Czabala, Monika Raj
Summary: In this study, the authors report a one-pot multicomponent Furan-Thiol-Amine reaction inspired by enzymes, which can generate stable pyrrole heterocycles independent of diverse functionalities. The reaction has wide applicability, including selective and irreversible labeling of peptides, synthesis of macrocyclic and stapled peptides, selective modification of different proteins with varying payloads, and labeling of lysine and cysteine in a complex human proteome.
NATURE COMMUNICATIONS
(2023)
Article
Chemistry, Multidisciplinary
Wan Pyo Hong, Van Hieu Tran, Hee-Kwon Kim
Summary: This method describes a facile one-pot synthesis of amides from N-Alloc-, N-Boc-, and N-Cbz-protected amines using isocyanate intermediates generated in situ, resulting in high yields of amides. It offers a promising approach for facile amidation.
Review
Chemistry, Multidisciplinary
Bauke Albada, Jordi F. Keijzer, Han Zuilhof, Floris van Delft
Summary: Click chemistry is a valuable method for chemical transformations, with oxidative processes leading to some of the fastest reactions known to date. One-pot click chemistry induced by oxidation conditions allows for sequential derivatization of molecules, offering a powerful approach for the preparation of high-performance materials and complex biomolecules, with potential for wider scope in the future.
Article
Chemistry, Multidisciplinary
Peisi Liao, Hongmei Liu, Chunmao He
Summary: In this study, we developed a reliable method for the synthesis of human SelF and described the synthetic route in detail. The synthesis involved a desulfurization process and removal of protective groups, resulting in the production of a large quantity of homogenous SelF. The reduction potential and oxidoreductase activity of SelF were determined, supporting its proposed function.
Article
Polymer Science
Tieshuai Zhao, Ben Drain, Gokhan Yilmaz, C. Remzi Becer
Summary: In this study, pentafluoro benzyl bromide was used as a clickable initiator for the cationic ring opening polymerization of poly(2-oxazolines) to synthesize various multiblock copolymers. By combining the para-fluoro-thiol click reaction with terminating agents in a one-pot approach, multiblock copolymers such as PEtOx-mb-PMeOx were successfully prepared. Characterization of the polymers was done using SEC, H-1 NMR, and MALDI-ToF mass spectrometry, and the self-assembly properties were studied using DLS and TEM, which showed nanoparticles with diameters ranging from 184 nm to 250 nm for the PEtOx-mb-PMeOx copolymers.
Article
Energy & Fuels
Dongyu Jin, Guojia Yu, Xinyu Li, Tenghui Li, Fan Zhang, Shichao Tian, Zhiyong Zhou, Zhongqi Ren
Summary: This study achieved deep desulfurization of fuel using a deep eutectic solvent. The L-Pyro/2TsOH/2PEG200 deep eutectic solvent showed excellent removal performance for aromatic sulfur compounds and maintained stability and reusability in multiple cycles.
Article
Chemistry, Multidisciplinary
Masanobu Nagano, Yichao Huang, Richard Obexer, Hiroaki Suga
Summary: This study presents a one-pot ribosomal synthesis method for the construction of macrocyclic depsipeptides, based on the SPCG motif. The ribosomal synthesis of linear peptides containing the SPCG motif with a backbone acyl donor thioester results in spontaneous conversion to corresponding cyclic depsipeptides.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Multidisciplinary
Arijit Jana, Madhuri Jash, Wakeel Ahmed Dar, Jayoti Roy, Papri Chakraborty, Ganesan Paramasivam, Sergei Lebedkin, Kaplan Kirakci, Sujan Manna, Sudhadevi Antharjanam, Jan Machacek, Monika Kucerakova, Sundargopal Ghosh, Kamil Lang, Manfred M. Kappes, Tomas Base, Thalappil Pradeep
Summary: This study presents a new class of thermally stable tetranuclear copper nanoclusters (Cu-4@oCBT, Cu-4@mCBT and Cu-4@ICBT) with tunable solid-state luminescence. They exhibit bright phosphorescence in their crystalline forms. Cu-4@oCBT and Cu-4@mCBT are green emitting, while Cu-4@ICBT is orange emitting. DFT calculations reveal the nature of their electronic transitions. Cu-4@oCBT and Cu-4@mCBT are thermally stable up to 400 degrees C, while Cu-4@ICBT is structurally flattened.
Article
Chemistry, Applied
Ayon Chatterjee, D. H. Sreenivasa Rao, Santosh Kumar Padhi
Summary: "In this study, a one-pot, two-step cascade reaction sequence was developed to convert benzylic alcohols to enantioenriched beta-nitroalcohols. By utilizing specific enzymes, high conversion rates and excellent stereoselectivity were achieved, demonstrating a new method for producing chiral pharmaceutical intermediates."
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Multidisciplinary
Ruiheng Jing, Wyatt C. Powell, Kyle J. Fisch, Maciej A. Walczak
Summary: We introduce a method for the direct conversion of alkyl thiols into boronic acids, which is characterized by its operational simplicity and compatibility with various functional groups present in peptides and proteins, making it a promising tool for late-stage functionalization.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Correction
Polymer Science
Aaron Priester, Jimmy Yeng, Krista Hilmas, Anthony J. J. Convertine
Summary: Priester et al. reported the one-pot synthesis of thiol-functional nanoparticles.
Article
Chemistry, Multidisciplinary
Dhanya Karipal Padinjare Veedu, Luke A. Connal, Lara R. Malins
Summary: In this study, an electrochemical method for peptide late-stage modification using amidic side-chains is developed. The method enables the modification of glutamine residues and the introduction of high-value functionalities through electroauxiliary-assisted oxidation. The applicability of the method to complex peptide systems is demonstrated, as well as its potential for peptide stapling and functionalization.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Biochemical Research Methods
Poanna Tran, Hue N. T. Tran, Kirsten L. McMahon, Jennifer R. Deuis, Lotten Ragnarsson, Alexander Norman, Simon J. Sharpe, Richard J. Payne, Irina Vetter, Christina I. Schroeder
Summary: This study aimed to design new bivalent inhibitors of Na(V)1.7 by combining the pore blocking activity of conotoxins with the gating modifier activity of spider toxins. The potency and selectivity of the resulting bivalent toxins were evaluated by ligating a conotoxin to a spider toxin. The bivalent peptide Pro[LPATG(6)]Sx, resulting from the ligation of ProTx-II and SxIIIC, showed the best combination with conserved potency at hNa(V)1.7.
BIOCONJUGATE CHEMISTRY
(2023)
Article
Biochemical Research Methods
Isabella R. Palombi, Nicole Lawrence, Andrew M. White, Caitlin L. Gare, David J. Craik, Brendan J. McMorran, Lara R. Malins
Summary: Targeted drug delivery with peptide-drug conjugates (PDCs) was investigated as an alternative antimalarial therapy. PDCs with low micromolar potency were developed by conjugating a synthetic peptide derived from an innate human defense molecule with the antimalarial drug primaquine (PQ). Various PDCs were designed to identify the optimal conjugation site and investigate linker length, hydrophilicity, and cleavability. Conjugation within a flexible spacer region of the peptide, with a cleavable linker to liberate the PQ cargo, was crucial for retaining the activity of both the peptide and drug.
BIOCONJUGATE CHEMISTRY
(2023)
Article
Chemistry, Medicinal
Kasuni B. Ekanayake, Mithun C. Mahawaththa, Haocheng Qianzhu, Elwy H. Abdelkader, Josemon George, Sven Ullrich, Rhys B. Murphy, Sarah E. Fry, Jason Johansen-Leete, Richard J. Payne, Christoph Nitsche, Thomas Huber, Gottfried Otting
Summary: N6-(((trimethylsilyl)-methoxy)carbonyl)-L-lysine (TMSK) and N6-trifluoroacetyl-L-lysine (TFAK) are non-canonical amino acids that can be incorporated into proteins via genetic encoding. A new aminoacyl-tRNA synthetase specific for N6-(((trimethylsilyl)methyl)-carbamoyl)-L-lysine (TMSNK) is described, which is chemically more stable than TMSK. The study demonstrates the use of these amino acids for site-specific NMR analysis of ligand binding to large proteins of limited stability and at low concentrations.
JOURNAL OF MEDICINAL CHEMISTRY
(2023)
Article
Chemistry, Organic
Joshua M. Hammond, Michael G. Gardiner, Lara R. Malins
Summary: A method for synthesizing amino acid sulfinate salts from commercially available alpha-chiral hydroxylated amino acids is presented. These reagents can serve as valuable precursors to alkyl radicals through mild photochemical oxidation. The resulting amino acid radicals readily react with alkyl and aryl disulfide radical traps, yielding a diverse range of modified amino acids.
Article
Chemistry, Organic
Hue N. T. Tran, Elena Budusan, Natalie J. Saez, Alexander Norman, Isaac J. Tucker, Glenn F. King, Richard J. Payne, Lachlan D. Rash, Irina Vetter, Christina I. Schroeder
Summary: Hi1a is a naturally occurring bivalent spider-venom peptide that shows promise for limiting ischemic damage. However, challenges in synthesizing and producing the peptide in large quantities have hindered progress in this area. Access to synthetic Hi1a is crucial for its development as a pharmacological tool and potential therapeutic.
Article
Chemistry, Organic
Dhanya Karipal Padinjare Veedu, Luke A. Connal, Lara R. Malins
Summary: In this study, we report the synthesis of second-generation glutamine building blocks with electroauxiliaries derived from 2,4-dimethoxythiophenyl and 2,4-dichlorothiophenyl. These building blocks improve the efficiency of solid-phase peptide synthesis and allow for fine-tuning of the electrochemical window for selective anodic oxidation reactions. The practical application of these new building blocks for iterative functionalizations is demonstrated by their installation onto a segment of involucrin, a protein component of human skin.
Article
Multidisciplinary Sciences
Tara K. Bartolec, Xabier Vazquez-Campos, Alexander Norman, Clement Luong, Marcus Johnson, Richard J. Payne, Marc R. Wilkins, Joel P. Mackay, Jason K. K. Low
Summary: Significant advances in cryoelectron microscopy have expanded our ability to create structural models of proteins and protein complexes. Cross-linking mass spectrometry (XL-MS) is demonstrated to be a powerful tool for high-throughput experimental assessment of protein structures and interactions. The combination of XL-MS data with AlphaFold2 predictions offers opportunities to explore the structural proteome and interactome in depth.
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA
(2023)
Article
Chemistry, Organic
Arthur H. Tang, Richard J. Payne
Summary: Gallinamide A, a natural product produced by cyanobacteria, shows potent anti-parasitic activity by inhibiting essential cysteine protease enzymes. It has also been found to possess strong antiviral activity against SARS-CoV-2 by covalently inhibiting the host cysteine protease cathepsin L involved in viral entry. To conduct detailed pre-clinical studies on its potential as a COVID-19 antiviral, a more efficient synthetic route was developed to obtain significant quantities of this natural product. The second generation total synthesis of Gallinamide A described here delivered the compound in a yield of 32% on a 315 mg scale over 16 steps (9 steps in the longest linear sequence).
Review
Chemistry, Multidisciplinary
Clara Bersi Motta Correa, Ana Carolina Kogawa, Marlus Chorilli, Herida Regina Nunes Salgado
Summary: Tyrosine sulfation is a post-translational modification that plays a crucial role in modulating the function of salivary proteins from blood feeding organisms. Utilizing synthetic chemistry, homogeneously sulfated peptides and proteins have been generated to study their structure and function. This research has provided valuable insights into the importance of tyrosine sulfate in enhancing anticoagulant activity.
ACCOUNTS OF CHEMICAL RESEARCH
(2023)
Article
Chemistry, Analytical
Evans C. Wralstad, Jessica Sayers, Ronald T. Raines
Summary: The main protease 3CL(pro) of SARS-CoV-2 is a dimeric enzyme that plays a crucial role in viral replication. This study used enzymatic methods to characterize the dimerization and catalytic efficiency of SARS-CoV-2 3CL(pro) and found that the enzyme forms a dimer at pH 7.5 with high catalytic activity. The enzymatic activity decreases in solutions of high ionic strength.
ANALYTICAL CHEMISTRY
(2023)
Article
Biochemistry & Molecular Biology
Cassidy Whitefield, Yen Vo, Brett D. Schwartz, Caryn Hepburn, F. Hafna Ahmed, Hideki Onagi, Martin G. Banwell, Keats Nelms, Lara R. Malins, Colin J. Jackson
Summary: Heparanase (HPSE) is an important enzyme involved in the degradation of heparan sulfate. Dysfunction of HPSE activity has been linked to various diseases, making it a target for therapeutic programs. Pentosan polysulfate sodium (PPS) is an FDA-approved drug that inhibits HPSE, but its mechanism of action is complex and challenging to characterize.
Article
Chemistry, Medicinal
Oliver H. Rathje, Lara Perryman, Richard J. Payne, Dieter W. Hamprecht
Summary: In this study, a novel approach called PROteolysis TArgeting Chimeras (PROTACs) was developed to effectively degrade MLKL and completely inhibit cell death. This work demonstrates the feasibility of targeting MLKL using a PROTAC approach and provides a powerful tool to further understand the role of MLKL within the necroptotic pathway.
JOURNAL OF MEDICINAL CHEMISTRY
(2023)
Article
Multidisciplinary Sciences
Shankar Raj Devkota, Pramod Aryal, Rina Pokhrel, Wanting Jiao, Andrew Perry, Santosh Panjikar, Richard J. Payne, Matthew C. J. Wilce, Ram Prasad Bhusal, Martin J. Stone
Summary: This study focused on a type of chemokine-binding proteins called A3 evasins from tick saliva, which can bind with CC chemokines and inhibit their receptor activation. Structure-based modifications of A3 evasins can alter their chemokine selectivity, suggesting their potential applications in targeted anti-inflammatory therapy.
NATURE COMMUNICATIONS
(2023)
Article
Chemistry, Medicinal
Kasuni B. Ekanayake, Mithun C. Mahawaththa, Haocheng Qianzhu, Elwy H. Abdelkader, Josemon George, Sven Ullrich, Rhys B. Murphy, Sarah E. Fry, Jason Johansen-Leete, Richard J. Payne, Christoph Nitsche, Thomas Huber, Gottfried Otting
Summary: TMSK, TMSNK, and TFAK are non-canonical amino acids that can be incorporated into proteins through genetic encoding. A new aminoacyl-tRNA synthetase specific for TMSNK is described, which is chemically more stable. Using the SARS-CoV-2 main protease (Mpro) as a model system, intense signals in the nuclear magnetic resonance (NMR) spectrum were observed for the trimethylsilyl and CF3 groups. The response of these groups to active-site ligands differed depending on their proximity to the active site, and the previously reported binding site of the ligand pelitinib was not confirmed.
JOURNAL OF MEDICINAL CHEMISTRY
(2023)
