Article
Chemistry, Multidisciplinary
Yiyin Xia, Janet To, Ning-Yu Chan, Side Hu, Heng Tai Liew, Seetharamsing Balamkundu, Xiaohong Zhang, Julien Lescar, Surajit Bhattacharjya, James P. Tam, Chuan-Fa Liu
Summary: This study found that Asn(OH) is an unnatural substrate for PALs, and successfully synthesized a new MMP2 inhibitor cyclic peptide using Asn(OH)-mediated cyclization, with the hydroxamic acid moiety as the key pharmacophore. Several bioactive Asp-containing cyclic peptides were also synthesized using this approach, demonstrating the effectiveness of substrate engineering in expanding the application of PAL ligation in the synthesis of therapeutic cyclic peptides.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Plant Sciences
Wenjuan Ding, Danmei Tian, Mei Chen, Zixuan Xia, Xiyang Tang, Sihao Zhang, Jihua Wei, Xunuo Li, Xinsheng Yao, Bin Wu, Jinshan Tang
Summary: LC-MS/MS-based molecular networking facilitated the discovery of seven new cyclopentapeptides, pseudoviridinutans A-F (1-7), from the marine-derived fungus Aspergillus pseudoviridinutans TW58-5. These compounds displayed a rare amino acid moiety, O,& beta;-dimethyltyrosine, which was observed for the first time from a marine-derived fungus. The planar structures of compounds 1-7 were elucidated through various spectroscopic analyses, and their absolute configurations were determined using Marfey's method and X-ray diffraction. Compound 6 exhibited significant anti-inflammatory activity by inhibiting the production of nitric oxide in LPS-induced murine macrophage RAW264.7 cells.
JOURNAL OF NATURAL PRODUCTS
(2023)
Review
Chemistry, Multidisciplinary
Takayuki Katoh, Hiroaki Suga
Summary: Genetic code manipulation allows the synthesis of peptide libraries with diverse nonproteinogenic amino acids, facilitating the discovery of bioactive peptides. Recent advancements in using engineered tRNAs have significantly improved the efficiency of incorporating D-, ss-, and gamma-amino acids into nascent peptides.
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN
(2021)
Review
Pharmacology & Pharmacy
Maria Gallo, Sira Defaus, David Andreu
Summary: G protein-coupled receptors (GPCRs) are usually described as monomeric transmembrane receptors, but increasing evidence shows that many GPCRs actually form higher-order assemblies. The formation, structure, physiological roles, and potential therapeutic applications of these assemblies are actively being explored. This review provides a comprehensive overview of GPCR complexes, with a focus on disrupting GPCRs using peptides mimicking transmembrane domains involved in multimerization. Recent strategies for developing drug-like versions of these transmembrane peptide candidates for therapeutic applications are also highlighted.
Article
Chemistry, Organic
Wei- Liao, Sih-Yu Lin, Yu-Shan Kuo, Chien-Fu Liang
Summary: Sodium thiosulfate is used as the sulfur source to react with anhydrides and then with phenols, enabling site-selective acylation of phenolic hydroxyl group in the presence of other alcoholic groups. This acylation method offers operational simplicity, high efficiency, and the use of odorless reagents with low toxicity.
Article
Chemistry, Analytical
Qingfang Niu, Pengyue Jin, Yu Huang, Lifang Fan, Caihong Zhang, Cheng Yang, Chuan Dong, Wenting Liang, Shaomin Shuang
Summary: In this study, a novel nanocomposite 3D-rGO/Pd@Au/CM-beta-CD was developed for the electrochemical enantiorecognition of tyrosine. Under the optimized determining conditions, this approach accurately determines the relative content of l- or d-Tyr enantiomers in a racemic solution.
Article
Biochemistry & Molecular Biology
Zhidong Chen, Yongxiao Li, Xinpei Wang, Xiaohui Qiu, Chenglin Wang, Zhe Wang, Xu Chen, Junqing Wang
Summary: In this study, a high-throughput molecular dynamics screening (HTMDS) process was proposed for the design of stable cyclic peptide (CP) binders using a combinatorial CP library composed of canonical and non-canonical amino acids. The methods were applied to design CP inhibitors for the bromodomain (BrD) of ATAD2B, and the results showed that CP-1(st).43 was the best CP candidate with an estimated Delta Gbind of -28.48 kcal/mol compared to the standard inhibitor C-38 which exhibited Delta Gbind of -17.11 kcal/mol.
JOURNAL OF BIOMOLECULAR STRUCTURE & DYNAMICS
(2023)
Article
Chemistry, Organic
Kiran Bajaj, Karishma Pidiyara, Shahid Khan, Prabhat N. Jha, Rajeev Sakhuja, Dalip Kumar
Summary: This study focused on the synthesis and characterization of fluorescent labeled glutamine and asparagine derivatives with high fluorescence quantum yields and excellent photostabilities using traceless Staudinger ligation. The successful permeation of these fluorescent amino acids into cellular components demonstrated their potential as fluorescent probes for chemical biology.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Joongoo Lee, Kevin J. Schwarz, Hao Yu, Antje Kruger, Eric Anslyn, Andrew D. Ellington, Jeffrey S. Moore, Michael C. Jewett
Summary: This study reports a method for fluorescent labeling of amino acids catalyzed by flexizyme, and demonstrates the site-specific incorporation of these fluorescent amino acids into peptides by the ribosome in vitro through genetic code reprogramming.
CHEMICAL COMMUNICATIONS
(2021)
Review
Biochemical Research Methods
Kuan-Lin Wu, Chenfei Yu, Catherine Lee, Chao Zuo, Zachary T. Ball, Han Xiao
Summary: Antibodies, particularly IgG, are widely used biomolecules in research, diagnostics, and therapy. To enhance their specificity, bioorthogonal handles have been introduced, showing advantages over traditional labeling methods. However, additional chemical treatment or protein engineering is still necessary for these site-specific modifications.
BIOCONJUGATE CHEMISTRY
(2021)
Article
Biochemistry & Molecular Biology
Yaxian Lin, Yangyang Jiang, Ziwei Zhao, Yueyang Lu, Xinping Xi, Chengbang Ma, Xiaoling Chen, Mei Zhou, Tianbao Chen, Chris Shaw, Lei Wang
Summary: Temporin-PKE is a novel peptide extracted from the skin secretion of Pelophylax kl. esculentus, which displays strong antimicrobial activity and cytotoxicity. Strategies for modifications include incorporating positively charged residues, D-amino acids, and altering the side chain amino acids. The optimal analogue, Temporin-PKE-3K, exhibits dual efficient functions, strong antimicrobial and anticancer activity.
Article
Chemistry, Multidisciplinary
Amanda A. Volk, Robert W. Epps, Milad Abolhasani
Summary: Microfluidic technologies have shown great potential in synthesis and optimization of various nanomaterials, but are not yet widely adopted in the colloidal nanomaterial community. By studying reactor design, performance, online diagnostics, and robotic experimentation strategies, controlled synthesis of colloidal nanomaterials can be accelerated. Collaborations between microfluidic reactor engineers and colloidal nanomaterial chemists can significantly expedite nanomaterial discovery, optimization, and manufacturing.
ADVANCED MATERIALS
(2021)
Article
Chemistry, Multidisciplinary
Daniel Fankhauser, Apostolos Alissandratos, Mantas Liutkus, Christopher J. Easton
Summary: The development of a new cleavable chloro amino acid to replace the relatively rare amino acid methionine greatly expands the scope of producible targets, allowing for simplified peptide synthesis despite the limitations posed by the natural abundance of aliphatic amino acids in proteins.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Multidisciplinary
Sahabaj Mondal, Surajit Singh, Ananda Shit, Santosh Kumar, Debasish Haldar
Summary: The tryptophan-mediated photo cleavage of disulfide bonds and resulting defibrillation process has been demonstrated. A supramolecular fiber-like network structure is formed through the self-assembly of dibenzyloxycarbonyl-L-cystine by non-covalent interactions, resulting in a hydrogel. The hydrogel shows thixotropic properties and is responsive to heat and pH. However, UV irradiation leads to disulfide bond cleavage, causing defibrillation and a gel-to-sol transition. The fiber exhibits amyloid-like structure and positive results in the Congo red assay.
NEW JOURNAL OF CHEMISTRY
(2022)
Article
Food Science & Technology
Simona Rinaldi, Sabrina Di Giovanni, Giuliano Palocci, Michela Conto, Roberto Steri, Carmela Tripaldi
Summary: This study investigated the impact of milk heat pre-treatment and pasteurization level on the protein digestibility of produced cheese. In vitro digestion method was used to analyze the peptide profile and amino acids released in digestion. The results showed the importance of heat treatment management on protein digestibility in soft cheese.
Review
Chemistry, Multidisciplinary
Claire Muzyka, Jean-Christophe M. Monbaliu
Summary: The previous decade has seen a significant increase in European incentives aimed at transitioning from a fossil fuel-based economy to a bio-based economy. Since 2012, various programs have been developed to promote research and innovation using sustainable and renewable resources. This review focuses on the most promising process conditions and technologies reported since 2012 for the conversion of bio-based vicinal diols into valuable industrial molecules.
Article
Chemistry, Multidisciplinary
Diana Silva-Brenes, Noemie Emmanuel, Vilmali Lopez Mejias, Jorge Duconge, Cornelis Vlaar, Torsten Stelzer, Jean-Christophe M. Monbaliu
Summary: This study demonstrates an improved synthesis method of Modafinil in a continuous flow reactor, achieving higher yield and purity with harmless by-products. The method also contributes to the development of an end-to-end pharmaceutical manufacturing system.
Article
Chemistry, Applied
Thomas Toupy, Jean-Christophe M. Monbaliu
Summary: This study describes the development of an intensified continuous flow process for the preparation of alkyl phosphonates. Through optimization, a high-yield and low environmental impact protocol was achieved, with the implementation of rapid optimization and process monitoring.
ORGANIC PROCESS RESEARCH & DEVELOPMENT
(2022)
Editorial Material
Biochemical Research Methods
Jean-Christophe M. Monbaliu, Julien Legros
Summary: The traditional paradigm of centralized, stepwise, large-scale chemical production has weaknesses and threats that are unsustainable. The emerging technology of microreactors offers a solution to these issues and enables safer and more reliable chemical production.
Article
Multidisciplinary Sciences
Vincent Girod, Robin Houssier, Karin Sahmer, Marie-Jose Ghoris, Stephanie Caby, Oleg Melnyk, Colette Dissous, Vincent Senez, Jerome Vicogne
Summary: This study reports a self-purifying microfluidic system that can select healthy adult worms and quickly identify molecules that act on schistosomiasis. This system allows for faster and more sensitive detection of antischistosomal compounds.
ROYAL SOCIETY OPEN SCIENCE
(2022)
Review
Infectious Diseases
Nina Compagne, Anais Vieira Da Cruz, Reinke T. Mueller, Ruben C. Hartkoorn, Marion Flipo, Klaas M. Pos
Summary: Antimicrobial resistance (AMR) is a major public health problem that has caused an estimated 4.95 million deaths in 2019. The overuse of antibiotics has led to the development of bacterial strains that are resistant to known antibiotics. Multidrug efflux pumps, which are naturally expressed by Gram-negative bacteria, play a central role in AMR. This review focuses on eight families of efflux pump inhibitors (EPIs) that have shown activity against Escherichia coli or Pseudomonas aeruginosa, providing insights into their structure-activity relationships, synthesis, in vitro and in vivo activities, pharmacological properties, binding sites, and mechanisms of action.
Article
Chemistry, Physical
Carlotta Campalani, Guillaume Petit, Jean-Christophe M. Monbaliu, Maurizio Selva, Alvise Perosa
Summary: Bass-CDs, synthesized from fishery waste, were used as a cheap and readily available photocatalyst in combination with oxygen and UV light for the efficient degradation of azo dyes. Both batch and continuous flow conditions were studied, and all the azo dyes were fully degraded, highlighting the suitability of bass-CDs for wastewater decontamination.
Article
Chemistry, Multidisciplinary
Remi Desmet, Celine Boidin-Wichlacz, Reda Mhidia, Aurelie Tasiemski, Vangelis Agouridas, Oleg Melnyk
Summary: One pillar of protein chemical synthesis is the selective desulfurization of cysteine residues into alanines, using ligation chemistries based on reactions involving phosphine as a sink for sulfur. This study demonstrates that cysteine desulfurization by a phosphine can be efficiently achieved using micromolar concentrations of iron under aerobic conditions in hydrogen carbonate buffer, reminiscent of iron-catalyzed oxidation phenomena occurring in natural waters. Therefore, this work highlights the potential of adapting chemical processes in aquatic systems for chemoselective transformations at the protein level, while minimizing the use of harmful chemicals.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
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, Organic
Benjamin Grain, Remi Desmet, Benoit Snella, Oleg Melnyk, Vangelis Agouridas
Summary: In this study, a latent and highly reactive oxalyl thioester precursor was efficiently introduced into a fully synthetic protein domain, serving as an on-demand reactive handle. This approach has potential applications in life or materials sciences.
Article
Chemistry, Multidisciplinary
Pauline Bianchi, Amaury Dubart, Maurane Moors, Damien Cornut, Gilbert Duhirwe, Jordi Ampurdanes Vilanova, Jean-Christophe M. Monbaliu
Summary: Estetrol is a natural biogenic estrogen that shows promise in hormonal-dependent treatments and oral contraception. This study focuses on the intensified synthesis of a key enone intermediate for estetrol preparation. By optimizing the process, the researchers achieved a high production yield and forecasted the potential for producing millions of doses.
REACTION CHEMISTRY & ENGINEERING
(2023)
Article
Chemistry, Multidisciplinary
Thibault Caradec, Ernesto Anoz-Carbonell, Ravil Petrov, Muriel Billamboz, Kevin Antraygues, Francois-Xavier Cantrelle, Emmanuelle Boll, Delphine Beury, David Hot, Herve Drobecq, Xavier Trivelli, Ruben C. Hartkoorn
Summary: Conjugation of antibiotics to siderophores facilitates the delivery of antibiotics into bacteria. Through genome analysis of a soil bacterium, a hybrid biosynthetic gene cluster responsible for the production of an antibiotic and a novel chlorocatechol-containing siderophore was discovered. It was found that the addition of ferric iron can induce conjugation of other cargo molecules to the siderophore, effectively entering bacteria and exhibiting antibiotic activity.
ACS CENTRAL SCIENCE
(2023)
Article
Chemistry, Multidisciplinary
Maxime Boddaert, Pauline Bianchi, Diana V. Silva-Brenes, Ancuta Musina, Marc Winter, Philippe M. C. Roth, Pierre-Yves Renard, Julien Legros, Jean-Christophe M. Monbaliu
Summary: This study introduces a new, efficient, safe, and sustainable flow protocol using ozone to oxidatively neutralize sulfur-based chemical warfare agent simulants. The combination of computational research and experimental validation has successfully achieved rapid neutralization under flow conditions.
Article
Chemistry, Multidisciplinary
Romain Morodo, Raphael Riva, Nynke M. S. van den Akker, Daniel G. M. Molin, Christine Jerome, Jean-Christophe M. Monbaliu
Summary: Polyphosphoesters have attracted renewed interest for biomedical applications due to their biocompatibility, degradability, and functionalities. However, their commercial use as biomaterials is limited by the difficult sourcing of their monomers and the corrosive nature of their intermediates. This study presents a groundbreaking approach for sourcing cyclic phosphate monomers using continuous flow technologies, which allows for safe and efficient synthesis of versatile cyclic phosphate monomers on a large scale.
Article
Chemistry, Multidisciplinary
Victor-Emmanuel H. Kassin, Diana Silva-Brenes, Thomas Bernard, Julien Legros, Jean-Christophe M. Monbaliu
Summary: This study reports the development of a continuous flow generator that produces highly reactive organic hypochlorites for the chemical neutralization of sulfur-based chemical warfare agent (CWA) simulants. The generator uses low environmental footprint resources and equipment, as well as widely available and cheap chemicals. The new neutralization protocol offers flexibility and efficiency.