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, 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.
Article
Chemistry, Multidisciplinary
Skander A. Abboud, Thomas Kodadek
Summary: This study presents an efficient method for generating on-resin dimers through self-condensation of 3,3-dimethoxypropionic acid-modified molecules, resulting in 2-pyridones. The approach demonstrated remarkable versatility by producing homodimers of peptides, peptoids, and non-peptidic ligands. Its ease of application, broad utility, and mild reaction conditions hold significance for peptide and peptoid research and offer potential for the on-resin development of a wide range of bivalent ligands.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Polymer Science
Damilola C. Akintayo, Beatriz G. de la Torre, Yongfu Li, Fernando Albericio
Summary: Amino-Li-resin is a novel polyacrylamide resin in fiber form, suitable for solid-phase peptide chemistry. It swells well in polar solvents, compatible with some non-polar solvents, and has high functional amino group loading for maximum peptide productivity. It exhibits excellent stability in both basic and acidic reagents, making it broadly applicable for biomolecule synthesis.
Article
Chemistry, Applied
Sinenhlanhla N. Mthembu, Amit Chakraborty, Ralph Schoenleber, Fernando Albericio, Beatriz G. de la Torre
Summary: Cysteine is an important amino acid in therapeutic peptides, and solid-phase peptide synthesis is commonly used for peptide preparation. However, the synthesis of C-terminal Cys peptide acids leads to a side reaction that produces three side products. In this study, we conducted a thorough investigation using a specific resin to minimize this side reaction and identified the optimal conditions.
ORGANIC PROCESS RESEARCH & DEVELOPMENT
(2022)
Review
Chemistry, Medicinal
Aizhan Abdildinova, Mark J. Kurth, Young-Dae Gong
Summary: Peptidomimetics are a unique class of drug molecules, and solid-phase synthesis is an important tool for synthesizing these molecules, where small molecules including heterocycles play a key role as drug cores.
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
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, Applied
Monika Kijewska, Michalina Zawadzka, Miko Laj, Piotr Stefanowicz
Summary: This study presents a fast, simple, and efficient method for the synthesis of lactosylated peptides using microwave-assisted synthesis and boronate affinity chromatography. The researchers successfully synthesized modified peptides from β-lactoglobulin and applied the functionalized resin for enrichment of lactosylated peptides in human serum albumin samples.
Review
Energy & Fuels
Marcio Jose da Silva, Neide Paloma Goncalves Lopes, Alana Alves Rodrigues
Summary: This article discusses the chemical transformation of glycerol to various compounds with high technological applications, especially in the fuel sector as bioadditives. The Keggin heteropolyacids (HPAs) are efficient catalysts in the syntheses of glycerol-derived bioadditives. However, their use as heterogeneous catalysts is hindered by their low surface area and solubility in polar solvents. Solid heteropoly salts, formed by converting HPAs to insoluble salts, have shown promise in reducing the cost and environmental impact of bioadditive synthesis processes.
Article
Chemistry, Multidisciplinary
Haoying Cao, Shanshan Ma, Yanhong Feng, Yawen Guo, Peng Jiao
Summary: Various beta-nitro ketones, including those with a beta-tertiary carbon, were synthesized through visible light photoredox catalysis, and can be easily converted into different organic compounds.
CHEMICAL COMMUNICATIONS
(2022)
Article
Biochemistry & Molecular Biology
Dayana Mesa, Yarelys E. Augusto, Giselle Hernandez, Juan P. Figueroa-Macias, Francisco Coll, Andres F. Olea, Maria Nunez, Hernan Astudillo Campo, Yamilet Coll, Luis Espinoza
Summary: Recent studies have shown that aza-steroids and steroidal sapogenins have antiproliferative and cytotoxic effects on human cancer cell lines, making them potential drug candidates for cancer treatment. This study synthesized new diosgenin oxime derivatives as potential antiproliferative agents and proposed a reaction mechanism to explain their transformation.
Review
Chemistry, Organic
Aizhan Abdildinova, Mark J. Kurth, Young-Dae Gong
Summary: Peptidomimetics are compounds with promising pharmacological properties that overcome limitations of peptides through backbone modifications. Accessible synthetic methodologies play a key role in peptidomimetic progress, with solid-phase organic synthesis serving as a powerful tool for their preparation. Numerous strategies for peptide backbone modifications via solid-phase synthesis have been developed in the last two decades.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Physical
M. V. Gorev, V. S. Bondarev, I. N. Flerov, K. Bormanis, E. Birks
Summary: Using the Landay thermodynamic potential, the T-E phase diagrams and electrocaloric effect in solid solutions (1-x)Pb(Ni1/3Nb2/3)O-3-xPbTiO3 (PNN-PT) were studied. The composition, temperature range, and electric field parameters significantly influenced the phase transitions, stability of crystalline phases, and electrocaloric properties. The intensive electrocaloric effect of the 0.8PNN-0.2PT compound indicates its potential as a solid-state refrigerant.
JOURNAL OF ALLOYS AND COMPOUNDS
(2022)
Article
Chemistry, Organic
Yuta Takeuchi, Kengo Akagawa, Kazuaki Kudo
Summary: Solid-phase biomimetic polyketide synthesis has been developed, which involves specific steps for carbon chain elongation and transformation to synthesize natural products, with monitoring and confirmation through colorimetric tests and NMR.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
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
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, Inorganic & Nuclear
Eman M. Fathalla, Morsy A. M. Abu-Youssef, Mona M. Sharaf, Ayman El-Faham, Assem Barakat, Matti Haukka, Saied M. Soliman
Summary: Two new Ni(II) complexes, [Ni(DMPT)(H2O)3](NO3)2.3H2O (1) and [Ni(DMPT)(H2O)3](NO3)2.H2O (2), were successfully synthesized using the hydrazine s-triazine ligand (E)-4,4'-(6-(2-(1-(pyridin-2-yl)ethylidene)hydrazinyl)-1,3,5-triazine-2,4-diyl)dimorpholine (DMPT) and a one-pot synthesis strategy. The structures of the complexes were characterized by elemental analysis, FTIR, and single-crystal X-ray diffraction analysis. The DMPT ligand acts as a tridentate NNN-chelate via three Ni-N coordination interactions, and the coordination sphere of the Ni(II) ion is completed by three water molecules. Both complexes exhibit distorted octahedral geometry. The crystal packing of the complexes is driven by strong O... H interactions, attributed to the presence of nitrate anions and water molecules. Complex 1 showed antimicrobial activity against both Gram-negative and Gram-positive bacterial strains, while the free ligand was inactive against all microbial species.
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.
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.
Review
Chemistry, Medicinal
Ghulam Shabir, Aamer Saeed, Wajeeha Zahid, Fatima Naseer, Zainab Riaz, Nafeesa Khalil, Mary J. Muneeba, Fernando Albericio
Summary: Fluorine substitution has been extensively explored for improving drug properties, such as increasing biological activity and enhancing stability. Selective substitution of fluorine onto therapeutic or diagnostic drugs can enhance pharmacokinetic and physicochemical properties. The use of fluorine in radiolabeling and PET imaging has also been studied. This review reports on FDA-approved fluorinated drugs and provides examples from various therapeutic and diagnostic drugs.
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
Biochemistry & Molecular Biology
Babita Kushwaha, Sinenhlanhla N. Mthembu, Anamika Sharma, Fernando Albericio, Beatriz G. de la Torre
Summary: We have synthesized disulfide-reducing agents DPDT and DMPDT from serinol and methyl serinol, respectively. DPDT demonstrated higher stability than DMPDT. The reducing capacity of DPDT was found to be comparable to that of DTT, and its effectiveness was evaluated in both liquid and solid phases.
Review
Chemistry, Multidisciplinary
K. P. Nandhini, Danah Al Shaer, Fernando Albericio, Beatriz G. G. de la Torre
Summary: Peptide Nucleic Acids (PNAs) are important mimics of DNA/RNA that can effectively bind with high affinity and specificity. Due to their metabolic stability, PNAs have broad applications in various fields. However, PNA synthesis faces challenges such as difficulties in preparing monomers and their solubility, as well as obstacles related to intra/inter chain aggregation and side reactions. Different protecting group strategies can be employed to overcome these hurdles and optimize the synthesis process.
CHEMICAL SOCIETY REVIEWS
(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.