Article
Chemistry, Multidisciplinary
Abigail Mae Clapperton, Katya Naomi Mariin Vera, Jon Babi, Helen Tran
Summary: This study demonstrates the successful replacement of hazardous and restricted solvents, DMF and NMP, with green and sustainable solvents for the synthesis of polypeptoids.
ACS SUSTAINABLE CHEMISTRY & ENGINEERING
(2023)
Article
Pharmacology & Pharmacy
Giovanni Vivenzio, Maria Carmina Scala, Pasquale Marino, Michele Manfra, Pietro Campiglia, Marina Sala
Summary: In recent years, peptides have become more successful as therapeutic compounds. The preferred method for obtaining peptides, solid-phase peptide synthesis (SPPS), does not follow the principles of green chemistry due to the use of toxic reagents and solvents. This study aimed to find an environmentally sustainable solvent to replace DMF in Fmoc SPPS. Dipropyleneglycol dimethylether (DMM), a green solvent with low toxicity and biodegradability, was tested for its applicability in various steps of SPPS. It was found that DMM is a valuable alternative to DMF in all steps of solid-phase peptide synthesis.
Article
Chemistry, Multidisciplinary
Peter H. G. Egelund, Sandip Jadhav, Vincent Martin, Henrik Johansson Castro, Franziska Richner, Sebastian Thordal Le Quement, Frank Dettner, Carolin Lechner, Ralph Schoenleber, Daniel Sejer Pedersen
Summary: This study explores the use of pyrrolidine as a base to expand the available solvent polarity space for green solid-phase peptide synthesis, investigating the effects of different solvent mixtures on Fmoc removal and coupling reactions, and comparing the synthesis results of different peptide targets.
ACS SUSTAINABLE CHEMISTRY & ENGINEERING
(2021)
Article
Chemistry, Multidisciplinary
Katarzyna Wegner, Danielle Barnes, Kim Manzor, Agnieszka Jardine, Declan Moran
Summary: The study aimed to find a greener solvent alternative to replace DMF in SPPS manufacturing processes at Ipsen. Greener solvents with efficient resin swelling and solubility were selected as candidates for SPPS trials in the small-scale synthesis of commercial and developmental peptides.
GREEN CHEMISTRY LETTERS AND REVIEWS
(2021)
Article
Chemistry, Multidisciplinary
Alexandra Tsouka, Pietro Dallabernardina, Marco Mende, Eric T. Sletten, Sabrina Leichnitz, Klaus Bienert, Kim Le Mai Hoang, Peter H. Seeberger, Felix F. Loeffler
Summary: Automated chemical synthesis has greatly simplified the synthesis of biopolymers in terms of method and speed, but parallel synthesis of oligosaccharides is currently not feasible. This study presents a chemical vapor glycosylation strategy that enables the simultaneous synthesis of oligosaccharides on a fixed cellulose membrane, allowing for flexible cleavage, purification, and characterization using different linkers. This method lays the foundation for the development of parallel automated glycan synthesis platforms.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Review
Chemistry, Analytical
Luana Bastos Santos, Rosivan Santos Assis, Jeferson Alves Barreto, Marcos Almeida Bezerra, Cleber Galvao Novaes, Valfredo Azevedo Lemos
Summary: In recent years, there has been a significant increase in the search for green chemistry principles in analytical methods. Solvents play a crucial role in green analytical chemistry, and certain criteria must be met for a solvent to be considered green, including availability, low toxicity, biodegradability, and low cost. However, the availability of green solvents is currently limited. Deep eutectic solvents (DESs) have emerged as a new and promising alternative to traditional solvents, attracting attention for their eco-friendly, inexpensive, and easily obtainable characteristics. This work provides a critical review of the use of DESs in liquid-phase microextraction (LPME) and their contributions to green chemistry.
TRAC-TRENDS IN ANALYTICAL CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Sandip Jadhav, Vincent Martin, Peter H. G. Egelund, Henrik Johansson Castro, Tobias Kruger, Franziska Richner, Sebastian Thordal Le Quement, Fernando Albericio, Frank Dettner, Carolin Lechner, Ralph Schonleber, Daniel Sejer Pedersen
Summary: Research demonstrates that green binary solvent mixtures are feasible alternatives to DMF in SPPS and can predict their utility in SPPS. Altering the composition of the binary solvent mixture can effectively reduce side-reactions in SPPS.
Review
Chemistry, Organic
Debora Procopio, Carlo Siciliano, Sonia Trombino, Denisa Elena Dumitrescu, Felicia Suciu, Maria Luisa Di Gioia
Summary: This review discusses literature from the past decade on strategies for reducing and replacing hazardous solvents, focusing on the use of biobased and neoteric solvents, such as ionic liquids and deep eutectic solvents, as greener alternatives for amide bond formation.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Dongkun Yu, Zhimin Xue, Tiancheng Mu
Summary: Deep eutectic solvents (DESs), as a class of green and easily modified solvents composed of monomers from biological sources, have been widely used in both laboratory and industrial scales. This review focuses on four strategies for materials synthesis using DESs: solvothermal methods, electrodeposition, calcination, and polymerization.
CELL REPORTS PHYSICAL SCIENCE
(2022)
Article
Chemistry, Multidisciplinary
Seang Uyin Hong, Yida Wang, Leong Sing Soh, Wai Fen Yong
Summary: This study integrated life cycle assessment (LCA) and techno-economic analysis (TEA) to evaluate the environmental and economic benefits of using green solvents in fabricating polyimide flat sheet membranes. The results showed that replacing the conventional solvent NMP with a less toxic green solvent can significantly reduce environmental impacts, but the production cost of green solvent DMSO is less competitive. Integrating the results from LCA and TEA, DMSO and EA were suggested as potential green solvents. The impact of synthesis approaches was negligible initially, but is expected to be more evident in larger-scale membrane production processes.
Review
Chemistry, Analytical
Alvaro Santana-Mayor, Ruth Rodriguez-Ramos, Antonio Herrera-Herrera, Barbara Socas-Rodriguez, Miguel Angel Rodriguez-Delgado
Summary: The development of sustainable chemistry has led to the emergence of new materials, with deep eutectic solvents (DESs) as a promising non-toxic alternative to toxic organic solvents, seeing a significant increase in their applications in analytical chemistry in recent years. The vast amount of information generated from studies associated with DESs needs continuous revision.
TRAC-TRENDS IN ANALYTICAL CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Jan Pawlas, Jon H. Rasmussen
Summary: This study demonstrates the feasibility of using Fmoc/t-Bu solid-phase peptide synthesis under aqueous conditions, utilizing a resin and solvent combination to improve resin swelling and solubility of starting materials. By developing a waste recycling method, the reuse of waste was achieved, reducing the amount of starting materials used and replacing hazardous solvents with an aqueous medium.
Review
Chemistry, Applied
Hong Yan, Fen-Er Chen
Summary: This review highlights the recent progress in solid-phase total synthesis of naturally occurring small peptides from 2014 to July 2021, which not only aids in the identification of peptide structures and synthesis of analogues, but also simplifies the isolation of intermediates.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Physical
Mengjin Zhou, Xiaomin Qiu, Yajuan Qu, Yangyang Liu, Zhaoyou Zhu, Yinglong Wang, Peizhe Cui, Jingwei Yang
Summary: In this study, deep-eutectic solvents (DESs) were used for the first time to separate the n-propanol/p-xylene/water ternary azeotrope system, and were compared with commonly used solvents. Quantum chemical calculations and experimental data were used to determine the interaction between the extractants and the system to be separated. The results showed that N-formylmorpholine (NFM) and cyclohexanol, (DL-Menthol/Lauric acid)2:1 (DES1) were the most effective extractants for component separation.
JOURNAL OF MOLECULAR LIQUIDS
(2023)
Article
Chemistry, Multidisciplinary
Mengqi Shen, Chao Yu, Huanqin Guan, Xiang Dong, Cooro Harris, Zhen Xiao, Zhouyang Yin, Michelle Muzzio, Honghong Lin, Jerome R. Robinson, Vicki L. Colvin, Shouheng Sun
Summary: Nanoparticle catalysts show promise in enabling multistep chemical reactions in a tandem fashion for green chemistry synthesis. Specifically, AuPd alloy NPs exhibit excellent catalytic performance in one-pot reactions to produce high-quality PBO, while Cu NPs can catalyze similar reactions to form PBO when formic acid is replaced.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Review
Biochemistry & Molecular Biology
Beatriz G. G. de la Torre, Fernando Albericio
Summary: While the world was battling with the COVID-19 Omicron wave at the end of 2021, except for China, most countries ended 2022 with COVID-19 being treated like the flu. As a result, the U.S. Food and Drug Administration (FDA) only authorized 37 new drugs this year, compared to an average of 52 in the previous four years. This marks the second lowest number of drug approvals in the last six years, even though it may change in the future. The decrease in FDA approvals mainly applies to small molecule drugs, while biologics and TIDES have remained relatively constant.
Review
Biochemistry & Molecular Biology
Fatima Tuz Zahra, Aamer Saeed, Khansa Mumtaz, Fernando Albericio
Summary: The tropylium ion is a versatile non-benzenoid aromatic species that serves as a catalyst in numerous organic transformations. It outperforms transition-metal catalysts with its yield, moderate conditions, non-toxic byproducts, functional group tolerance, selectivity, and ease of handling. This review highlights the importance of the tropylium ion as an environmentally safe catalyst and summarizes its role in various organic reactions.
Article
Chemistry, Multidisciplinary
Sisa Chalan-Gualan, Ivan Ramos-Tomillero, Thibault Terencio, Lola De Lima, Daniela G. Navas-Leon, Margarita Suarez, Nelson Santiago Vispo, Fernando Albericio, Hortensia Rodriguez
Summary: Cysteine-based perfluoroaromatic compounds, such as hexafluorobenzene (HFB) and decafluorobiphenyl (DFBP), were synthesized and used as versatile cores to construct molecular systems with interesting properties. DFBP was found to be more effective than HFB for the monoalkylation of thiols. Antibody-perfluorinated conjugates were prepared using thiol through two different strategies, demonstrating that bioconjugation did not affect the macromolecular entity. Spectroscopic characterization and theoretical calculations were used to evaluate the molecular properties of the synthesized compounds. Molecular docking predicted that cysteine-based DFBP derivatives could be potential binders for topoisomerase II alpha and COX-2, suggesting their potential as anticancer agents and candidates for anti-inflammatory treatment.
Article
Crystallography
Hessa H. H. Al-Rasheed, Sarah A. A. AL-khamis, Assem Barakat, Ayman El-Faham, Matti Haukka, Saied M. M. Soliman
Summary: A series of novel isatin-s-triazine hydrazone derivatives were synthesized and characterized. The synthetic method involved the reaction of s-triazine hydrazine precursors with isatin derivatives, which resulted in the formation of target products 6a-e with high yields and purities. The crystal structure analysis of compound 6c revealed the presence of significant non-covalent interactions.
Article
Crystallography
Amal Yousri, Ayman El-Faham, Matti Haukka, Mohammed Salah Ayoup, Magda M. F. Ismail, Nagwan G. El Menofy, Saied M. Soliman, Lars Ohrstrom, Assem Barakat, Morsy A. M. Abu-Youssef
Summary: The novel [Na(bpmt)(2)][AuCl4] complex was synthesized using the self-assembly method with the pincer ligand 2,4-bis(3,5-dimethyl-1H-pyrazol-1-yl)-6-methoxy-1,3,5-triazine (bpmt). The complex exhibited a distorted octahedral geometry around the Na(I) ion, with two bpmt ligands meridionally coordinated via short and slightly longer Na-N bonds. The complex showed significant antibacterial and antifungal activities, with enhanced efficacy compared to free bpmt and a positive control Amoxicillin for most tested bacteria, as well as better antifungal efficacy against C. albicans compared to bpmt.
Article
Chemistry, Medicinal
Othman Al Musaimi, Danah Al Shaer, Fernando Albericio, Beatriz G. de la Torre
Summary: In 2022, a total of 37 new drug entities were approved, with TIDES class drugs gaining five authorizations, consisting of four peptides and one oligonucleotide. The majority of these drugs (23 out of 37) were first-in-class and received fast-track designation by the FDA. This analysis focuses on the TIDES approved in 2022, examining their chemical structure, medical target, mode of action, administration route, and common adverse effects.
Article
Biotechnology & Applied Microbiology
Fanny Guzman, Monica Arostica, Tanya Roman, Dina Beltran, Adriana Gauna, Fernando Albericio, Constanza Cardenas
Summary: Solid-Phase Peptide Synthesis (SPPS) is a widely used technique in research and production. Three different laboratory protocols have been implemented to fulfill diverse requirements. The results show that each protocol yields different purification and can be chosen based on specific needs.
ELECTRONIC JOURNAL OF BIOTECHNOLOGY
(2023)
Article
Biochemistry & Molecular Biology
Sinenhlanhla N. Mthembu, Amit Chakraborty, Ralph Schonleber, Fernando Albericio, Beatriz G. de la Torre
Summary: Morpholine, scoring 7.5 in greenness and not being regulated, is a promising candidate for Fmoc removal in solid-phase peptide synthesis (SPPS). Morpholine in dimethylformamide (DMF) (50%-60%) effectively removes Fmoc in SPPS, reduces diketopiperazine formation, and nearly eliminates aspartimide formation. Somatostatin has been successfully synthesized using 50% morpholine in DMF with the same purity as when using 20% piperidine-DMF, serving as proof of concept.
JOURNAL OF PEPTIDE SCIENCE
(2023)
Review
Biochemistry & Molecular Biology
Umair Rauf, Ghulam Shabir, Saba Bukhari, Fernando Albericio, Aamer Saeed
Summary: This paper summarizes the recent advancements in the synthesis and applications of ferrocene derivatives reported from 2016 to date. It focuses on the synthesis of diverse classes of organic compounds with ferrocene scaffolds and the development of applications of ferrocene-based organometallic compounds, particularly in the fields of biology, medicine, bio-sensing, chemosensing, asymmetric catalysis, materials, and industry.
Review
Chemistry, Multidisciplinary
Jessica T. Mhlongo, Ayman Y. Waddad, Fernando Albericio, Beatriz G. de la Torre
Summary: Antimicrobial peptides (AMPs) are promising candidates for combating multidrug resistance due to their heterogenous structures and broad-spectrum action. The combined use of AMPs with other antimicrobial agents provides a new arsenal of drugs with synergistic action, inhibiting the development of drug resistance. This review discusses various synergies of AMPs with antimicrobials and miscellaneous agents, providing guidance for improved clinical outcomes.
Article
Crystallography
Saied M. Soliman, Ayman El-Faham, Assem Barakat, Alexandra M. Z. Slawin, John Derek Woollins, Morsy A. M. Abu-Youssef
Summary: Through X-ray crystallography, we synthesized and elucidated the structures of two IIB group complexes [Cd(DMPT)Cl-2] (6) and [Zn(DMPT)Cl-2] (7). Both complexes crystallized in the monoclinic crystal system, with different lattice parameters. Complex 6 exhibited a square pyramidal coordination environment, while complex 7 showed an intermediate between trigonal bipyramidal and square pyramidal coordination. Hirshfeld calculations revealed that hydrogen bonding interactions played a significant role in the supramolecular structure of both complexes.
Article
Chemistry, Inorganic & Nuclear
Hessa H. Al-Rasheed, Sarah A. AL-khamis, Ayman El-Faham, Assem Barakat, Alexandra M. Z. Slawin, John Derek Woollins, Saied M. Soliman
Summary: The unexpected tetranuclear [Cu-4(DPPT)(2)Cl-6] complex was obtained through self-assembly, and it showed good antifungal and antibacterial activity against Gram-positive bacteria.
Article
Biochemical Research Methods
Tanya Roman, Gerardo Acosta, Beatriz G. de la Torre, Constanza Cardenas, Fanny Guzman, Fernando Albericio
Summary: This study presents an optimized procedure for activating 2-chlorotrityl chloride (2-CTC) resin, reducing the use of activation reagent and activation time. It also demonstrates the feasibility of reusing the resin and achieving different degrees of activation by varying the amount of thionyl chloride (SOCl2).
METHODS AND PROTOCOLS
(2023)
Article
Chemistry, Organic
K. P. Nandhini, Sikabwe Noki, Edikarlos Brasil, Fernando Albericio, Beatriz G. de la Torre
Summary: Peptide Nucleic Acids (PNAs) are a class of synthetic biomolecules with great potential in medicine. A new PNA SPS strategy based on a safety-catch protecting group scheme has been developed, allowing the synthesis of PNAs using Boc as a temporal protecting group.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Rafel Prohens, Rafael Barbas, Beatriz G. de la Torre, Fernando Albericio, Antonio Frontera
Summary: This article reports on the crystal structure and properties of Oxyma-B, an important racemization suppressor for peptide synthesis. Through a combination of experimental and computational methods, the solid-state landscape and hydration tendency of this substance have been revealed.