Article
Chemistry, Medicinal
Shaowei Bo, Dong Zhang, Mengjie Ma, Xukai Mo, Julia Stabinska, Michael T. McMahon, Changzheng Shi, Liangping Luo
Summary: Chemical exchange saturation transfer (CEST) MRI is a versatile molecular imaging approach that has great potential for clinical translation. DiaCEST agents, such as glucose, glycogen, glutamate, creatine, and nucleic acids, are attractive due to their excellent biocompatibility and potential for biodegradation. However, the sensitivity of most diaCEST agents is limited by their small chemical shifts from water. In this study, we investigated the CEST properties of acyl hydrazides with different substitutions and expanded the catalog of diaCEST agents with larger chemical shifts. Our study shows the potential of these agents in cancer diagnosis.
Article
Chemistry, Organic
Xiao-Lei Xie, Jing-Ze Qi, Xiao-Cui Wan, Suo-De Zhang, Yan-Ni Zhang, Ge-Min Fang
Summary: We present a robust and practical method for chemical protein synthesis using an o-nitrobenzyl group as a temporary protective group. Through further investigation, we establish a reliable strategy for the quantitative photodeprotection of the o-nitrobenzyl group. This stable protective group is successfully applied in the chemical synthesis of a programmed death ligand 1 fragment, providing a practical approach for hydrazide-based native chemical ligation.
Article
Chemistry, Multidisciplinary
William Gagne-Monfette, Jean-Francois Vincent-Rocan, Owen C. Lutes, Genevieve F. O'Keefe, Alexandria D. M. Jeanneret, Claire Blanger, Ryan A. Ivanovich, Andre M. Beauchemin
Summary: This study explores the application of amido-isocyanates in synthesizing aza-tripeptides and hydantoins, where the formed oxadiazolone can block N-isocyanate traces, leading to moderate to high yields under specific reaction conditions when using organic bases as catalysts. Further confirmation of an amido-isocyanate intermediate was achieved by utilizing carboxylic acids as nucleophiles to produce N-acylhydrazide products.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Multidisciplinary Sciences
Nathalie Ollivier, Magalie Senechal, Remi Desmet, Benoit Snella, Vangelis Agouridas, Oleg Melnyk
Summary: Phosphorylation is a mechanism used by cells to promote protein-biomolecule association. In this study, the authors demonstrate the effects of interactions between proteins equipped with positively charged arginines and peptides harboring negatively charged phosphoserines, enabling rate acceleration and chemical processes under dilute conditions.
NATURE COMMUNICATIONS
(2022)
Article
Chemistry, Organic
Nathalie Ollivier, Eliott Roy, Vangelis Agouridas, Vincent Diemer, Oleg Melnyk
Summary: 4-Mercaptophenylacetic acid (MPAA) is a commonly used catalyst for native chemical ligation (NCL), but it requires a large excess for practical rates (up to 50-100 equivalents). In this study, we found that the catalytic potency of MPAA can be enhanced by introducing a stretch of arginines in the departing thiol of the thioester. This electrostatically assisted NCL reaction allows for rapid synthesis using substoichiometric concentrations of MPAA, which is advantageous for practical applications.
Article
Chemistry, Multidisciplinary
Sebastian Trunschke, Emanuele Piemontese, Olaf Fuchs, Skander Abboud, Oliver Seitz
Summary: By introducing new ligation auxiliaries, this study expands the applicability of native chemical ligation and investigates the role of the pyridine-ring nitrogen in the auxiliaries. The study successfully synthesizes peptides with special structures, demonstrating that the new auxiliary has increased stability and wide application potential.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Chemistry, Multidisciplinary
Evelyn M. Molloy, Maria Dell, Veit G. Haensch, Kyle L. Dunbar, Romy Feldmann, Ansgar Oberheide, Lydia Seyfarth, Jana Kumpfmueller, Therese Horch, Hans-Dieter Arndt, Christian Hertweck
Summary: This study reports the discovery of a genuine chemical mediator, homodetic cyclopeptide (cAIP), that controls endospore formation in clostridia, and reveals a widespread feature of clostridial AIP biosynthesis, namely the novel enzyme-primed, intramolecular native chemical ligation (NCL).
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Richard Houska, Marvin Bjorn Stutz, Oliver Seitz
Summary: The study presents a reaction system for synthesizing Bcr-Abl tyrosine kinase inhibitors in water using native chemical ligation to form benzanilides. This method was successfully applied for the synthesis of thiolated ponatinib and GZD824 derivatives, with only a moderate effect on the affinity for Abl1 kinase. Nucleic acid-templated benzanilide formation could potentially find application in DNA-encoded combinatorial libraries for drug discovery.
Article
Chemistry, Organic
Dipankar Chaudhuri, Rajasekaran Ganesan, Alicia Vogelaar, Mansour A. Dughbaj, Paul M. Beringer, Julio A. Camarero
Summary: A new epimerization-free approach for the Fmoc-based synthesis of murepavadin using intramolecular native chemical ligation and desulfurization reaction has been developed, resulting in a high yield of bioactive murepavadin in two steps. The synthetic peptide antibiotic showed potent activity against different clinical isolates of P. aeruginosa. This approach can be easily adapted for the production of murepavadin analogues and other backbone-cyclized peptides.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Cheng-Ting Shih, Bo-Hong Kuo, Chun-Yi Tsai, Mei-Chun Tseng, Jiun-Jie Shie
Summary: This study demonstrates that dibenzocyclooctendiones (DBCDOs) are efficient chemical reagents for the site-specific labeling of arginine-containing biomolecules. DBCDOs undergo an irreversible ring-contracted rearrangement with the guanidinium group on arginine residues under mild reaction conditions, resulting in regioselective dual-labeled arginine residues.
Article
Polymer Science
Subhajit Pal, Ankita Mandal, Linda Hong, Roberto D. Ortuso, Alke Petri-Fink, Stefan Salentinig, Andreas F. M. Kilbinger
Summary: Native chemical ligation (NCL) is an excellent and efficient method for the chemical synthesis of proteins and peptides from unprotected short peptide fragments. It offers high chemo- and regioselectivity, allowing the synthesis of functional biomacromolecules without protection-deprotection strategies under mild conditions. In this study, the potential of NCL for non-natural polymer conjugation was explored, and diblock and ABA triblock copolymers were synthesized with high efficiency. The successful synthesis of non-natural polymers using NCL was confirmed by size exclusion chromatography and NMR spectroscopy analysis.
Article
Chemistry, Multidisciplinary
Luisa Maria Gatzemeier, Franc Meyer, Ulf Diederichsen, Tiago Fleming Outeiro
Summary: Alpha-Synuclein is a protein involved in neurodegenerative disorders that accumulate in brain protein inclusions. We have developed a chemical synthesis method for Alpha-Synuclein, allowing the synthesis of protein variants for further investigation of its structure and aggregation behavior.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Biochemical Research Methods
Tomislav Caval, Alexander Buettner, Markus Haberger, Dietmar Reusch, Albert J. R. Heck
Summary: Glycosylation plays a critical role in biotherapeutics, and by comparing different analytical methods for glycosylation profiling, we found that using a combination of native mass spectrometry and bottom-up glycoproteomics offers superior characterization of glycosylated biotherapeutics. This approach allows for direct information about glycosite localization and helps in the characterization of glycoengineered proteins and other complex biotherapeutics.
JOURNAL OF THE AMERICAN SOCIETY FOR MASS SPECTROMETRY
(2021)
Article
Chemistry, Multidisciplinary
Olaf Fuchs, Sebastian Trunschke, Hendrik Hanebrink, Marc Reimann, Oliver Seitz
Summary: This study introduces a new auxiliary, MPyE, designed to catalyze ligation reactions in chemical protein synthesis. The MPyE auxiliary proves to be effective in providing useful rates even for junctions containing proline or a beta-branched amino acid.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Wei-Wei Shi, Chaowei Shi, Tong-Yue Wang, Yu-Lei Li, Yong-Kang Zhou, Xu-Han Zhang, Donald Bierer, Ji-Shen Zheng, Lei Liu
Summary: The chemical synthesis of correctly folded proteins with multiple or interchain disulfide bonds was expedited using a removable glycosylation modification (RGM) strategy, which introduces O-linked beta-N-acetylglucosamine (O-GlcNAc) groups to improve folding and can be efficiently removed afterwards.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Correction
Chemistry, Multidisciplinary
Vijay Chudasama, Antoine Maruani, Stephen Caddick
Article
Chemistry, Organic
Mauricio Morais, Joao P. M. Nunes, Kersti Karu, Nafsika Forte, Irene Benni, Mark E. B. Smith, Stephen Caddick, Vijay Chudasama, James R. Baker
ORGANIC & BIOMOLECULAR CHEMISTRY
(2017)
Article
Chemistry, Multidisciplinary
Maximillian T. W. Lee, Antoine Maruani, Daniel A. Richards, James R. Baker, Stephen Caddick, Vijay Chudasama
Article
Chemistry, Multidisciplinary
Eifion Robinson, Joao P. M. Nunes, Vessela Vassileva, Antoine Maruani, Joao C. F. Nogueira, Mark E. B. Smith, R. Barbara Pedley, Stephen Caddick, James R. Baker, Vijay Chudasama
Article
Chemistry, Multidisciplinary
Joao P. M. Nunes, Vessela Vassileva, Eifion Robinson, Mauricio Morais, Mark E. B. Smith, R. Barbara Pedley, Stephen Caddick, James R. Baker, Vijay Chudasama
Editorial Material
Chemistry, Multidisciplinary
Stephen Caddick
NATURE REVIEWS CHEMISTRY
(2017)
Editorial Material
Chemistry, Multidisciplinary
Stephen Caddick
NATURE REVIEWS CHEMISTRY
(2017)
Article
Chemistry, Organic
Calise Bahou, Daniel A. Richards, Antoine Maruani, Elizabeth A. Love, Faiza Javaid, Stephen Caddick, James R. Baker, Vijay Chudasama
ORGANIC & BIOMOLECULAR CHEMISTRY
(2018)
Review
Chemistry, Multidisciplinary
Sameer S. Kulkarni, Jessica Sayers, Bhavesh Premdjee, Richard J. Payne
NATURE REVIEWS CHEMISTRY
(2018)
Article
Biochemistry & Molecular Biology
Sebastien R. G. Galan, James R. Wickens, Jitka Dadova, Wai-Lung Ng, Xinglong Zhang, Robert A. Simion, Robert Quinlan, Elisabete Pires, Robert S. Paton, Stephen Caddick, Vijay Chudasama, Benjamin G. Davis
NATURE CHEMICAL BIOLOGY
(2018)
Article
Biochemical Research Methods
Sameer S. Kulkarni, Emma E. Watson, Bhavesh Premdjee, Kilian W. Conde-Frieboes, Richard J. Payne
Article
Multidisciplinary Sciences
Emma E. Watson, Jorge Ripoll-Rozada, Ashley C. Lee, Mike C. L. Wu, Charlotte Franck, Tim Pasch, Bhavesh Premdjee, Jessica Sayers, Maria F. Pinto, Pedro M. Martins, Shaun P. Jackson, Pedro Jose Barbosa Pereira, Richard J. Payne
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA
(2019)
Article
Chemistry, Organic
Xiaoyi Wang, Leo Corcilius, Bhavesh Premdjee, Richard J. Payne
JOURNAL OF ORGANIC CHEMISTRY
(2020)
Article
Chemistry, Multidisciplinary
Bhavesh Premdjee, Asser S. Andersen, Mark Larance, Kilian W. Conde-Frieboes, Richard J. Payne
Summary: The text discusses the successful assembly of a 31.5 kDa phosphorylated IGFBP-2 protein using two ligation manifolds, incorporating phosphoserine post-translational modification and nine disulfide bonds.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Multidisciplinary
Cameron C. Hanna, Sameer S. Kulkarni, Emma E. Watson, Bhavesh Premdjee, Richard J. Payne
CHEMICAL COMMUNICATIONS
(2017)
