Article
Chemistry, Organic
Yaroslav Verkh, Ona Illa, Rosa M. Ortuno
Summary: Chiral scaffolds have been synthesized from conveniently protected cyclobutane beta-amino acids through selective transformations, presenting additional functional groups and high versatility for the production of polyfunctional chemical platforms. These molecules can be used as chiral precursors for the synthesis of complex molecules.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Yi Jiang, Quanquan Wang, Xinglong Zhang, Ming Joo Koh
Summary: This study presents a Ti-catalyzed regime for the efficient synthesis of a wide range of C-alkyl glycosides through stereocontrolled glycosyl radical addition. By using alkynes as radical acceptors, the synthesis of C-alkenyl glycosides bearing a Z olefin appendage is achieved. Mechanistic and computational studies elucidate the unexpected reactivity of glycosyl chlorides in the presence of an organotitanium complex. The utility of this protocol is demonstrated through the concise preparation of therapeutically important carbohydrates and glycopeptide conjugates.
Review
Chemistry, Multidisciplinary
Francisco Jose Aguilar Troyano, Kay Merkens, Khadijah Anwar, Dr Adrian Gomez-Suarez
Summary: Amino acids are key structural motifs widely used in organic synthesis, biochemistry, and material sciences. Radical chemistry strategies for the synthesis and modification of amino acids have gained increased attention in recent years, providing rapid access to libraries of novel unnatural amino acids containing a wide range of structural motifs.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Danim Lim, Wonchul Lee, Jungwoo Hong, Jintaek Gong, Jonghoon Choi, Jaewook Kim, Seolhee Lim, Sung Hyun Yoo, Yunho Lee, Hee-Seung Lee
Summary: We introduce a novel cyclic β-amino acid, trans-(3S,4R)-4-aminotetrahydrothiophene-3-carboxylic acid (ATTC), as a versatile building block for designing peptide foldamers with controlled secondary structures. Our findings reveal that ATTC-containing foldamers can adopt 12-helical conformations similar to their isosteres and offer the possibility of fine-tuning their properties via post-synthetic modifications. In particular, chemoselective conjugation strategies demonstrate that ATTC provides unique post-synthetic modification opportunities, which expand their potential applications across diverse research areas.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Xingyue Li, Andrew L. Sabol, Patrick J. Salveson, James S. Nowick
Summary: Researchers have developed a new beta-turn template, (delta)MeOrn, which can induce a beta-hairpin conformation in peptides. This template demonstrates superior folding compared to (delta)Orn and is comparable to d-Pro-Gly.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Review
Chemistry, Inorganic & Nuclear
Dmitry A. Gruzdev, Galina L. Levit, Victor P. Krasnov, Valery N. Charushin
Summary: This review highlights the increasing interest in derivatives of dicarba-closo-dodecaboranes and dicarba-nido-undecaboranes (carboranes) for modern medicinal chemistry and materials science. It discusses the combination of carborane residues and amino acid fragments to obtain promising medicinal agents and unique materials, as well as the preparation and applications of compounds combining amino acid and peptide residues with carborane clusters. Special attention is given to the preparation of enantiopure conjugates and the chirality origins in these compounds, aiming to stimulate further fundamental research in this field.
COORDINATION CHEMISTRY REVIEWS
(2021)
Article
Chemistry, Organic
Yudai Shinkawa, Toshiki Furutani, Takumi Ikeda, Mugen Yamawaki, Toshio Morita, Yasuharu Yoshimi
Summary: The side-chain functionalization of aspartic/glutamic acid derivatives was achieved through photoinduced decarboxylation using organic two-molecule photoredox catalysts without racemization under mild conditions. A facile process involving the preparation of substrates and photoinduced decarboxylative radical additions provides easy access to the linked amino acids with carbohydrates and amino acids at the side chain.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Pablo Tovillas, Claudio D. Navo, Paula Oroz, Alberto Avenoza, Francisco Corzana, Maria M. Zurbano, Gonzalo Jimenez-Oses, Jesus H. Busto, Jesus Peregrina
Summary: Chiral bicyclic N,O-acetal isoserine derivatives have been synthesized using acid-catalyzed reactions, which have significant applications in peptidomimetic and medicinal chemistry.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Review
Biochemistry & Molecular Biology
Wayiza Masamba
Summary: This review discusses the widespread applications of alpha-amino acids in various areas and compares the differences and similarities between the Petasis and Strecker reactions, two of the most widely used protocols for their synthesis.
Review
Chemistry, Organic
Massimo Serra, Marco Terreni, Eric Bernardi, Lino Colombo
Summary: After their first synthesis in 1994, azabicycloalkane amino acids have gained increasing interest and become one of the most important classes of constrained dipeptide mimics. Incorporating them into peptidomimetic structures has allowed the synthesis of a wide range of biologically active compounds. However, methods for obtaining functionalized and easy-to-functionalize derivatives of these amino acids are still limited. This review focuses on the synthesis of functionalized azabicycloalkane amino acids from 2010 to the present, and discusses their recent applications in drug discovery.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Feng Zhu, Eric Miller, Wyatt C. Powell, Kelly Johnson, Alexander Beggs, Garrett E. Evenson, Maciej A. Walczak
Summary: In this study, we demonstrate that Ala(B) can serve as universal building blocks for the synthesis of modified amino acids, peptides, and proteins. We show its compatibility with common peptide chemistry techniques and its participation in Pd-catalyzed reactions. This highlights the practical applicability of Ala(B) synthons in accessing modified peptides and proteins, as well as the synthesis of cyclic/stapled peptides.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Physical
Munirah M. Al-Rooqi, Ehsan Ullah Mughal, Qandeel Alam Raja, Rami J. Obaid, Amina Sadiq, Nafeesa Naeem, Jihan Qurban, Basim H. Asghar, Ziad Moussa, Saleh A. Ahmed
Summary: This review provides a comprehensive overview of the synthesis, peptide incorporation, and biological applications of pipecolic acid (Pip) and its derivatives. Pip, a cyclic non-protein amino acid derived from L-lysine, has gained interest in the pharmaceutical and chemical industries.
JOURNAL OF MOLECULAR STRUCTURE
(2022)
Article
Chemistry, Organic
Ayumi Uchino, Chihiro Tsukano, Tsuneo Imamoto, Kazuhiro Irie
Summary: Two new alkyl bridged-tris-alpha-amino acids with Fmoc protecting groups have been designed and synthesized as new flexible linkers for trimer models, providing an alternative approach to mimic trimers with higher flexibility than reported options.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Physical
Maheshwerreddy Chilamari, Jacob R. Immel, Pei-Hsuan Chen, Bayan M. Alghafli, Steven Bloom
Summary: By combining a biocompatible flavin photocatalyst with a palladium catalyst, the study achieved the construction of isotopically enriched peptidomimetics and other synthetic reactions in water. The ligand and palladium oxidation state played crucial roles in controlling product selectivity during synthetic peptide construction.
Article
Chemistry, Multidisciplinary
Sukriye Cakmak, Sevgi Kansiz, Mohammad Azam, Cem Cuneyt Ersanli, Onder Idil, Aysel Veyisoglu, Hasan Yakan, Halil Kutuk, Arunabhiram Chutia
Summary: A novel heterocyclic amide derivative was synthesized and investigated for its significant antioxidant and antimicrobial properties through experimental and computational studies.
Article
Oncology
Luigi Ippolito, Giuseppina Comito, Matteo Parri, Marta Iozzo, Assia Duatti, Francesca Virgilio, Nicla Lorito, Marina Bacci, Elisa Pardella, Giada Sandrini, Francesca Bianchini, Roberta Damiano, Lavinia Ferrone, Giancarlo la Marca, Sergio Serni, Pietro Spatafora, Carlo V. Catapano, Andrea Morandi, Elisa Giannoni, Paola Chiarugi
Summary: This research reveals that lactate can promote lipid metabolism in prostate cancer cells through the regulation of gene expression, thus contributing to cancer progression and metastasis.
Article
Biochemistry & Molecular Biology
Lorenzo Baldini, Elena Lenci, Francesca Bianchini, Andrea Trabocchi
Summary: Molecular targets in tumor angiogenesis include VEGF, integrin receptors, and MMPs. Inhibiting these targets can help block tumor cell invasion and metastasis. Combining the inhibition of alpha(v)beta(3) and MMP2 as a multitarget approach can deliver a synergistic blockade of tumor cell migration, invasion, and metastasis.
Article
Biochemistry & Molecular Biology
Lorenzo Calugi, Elena Lenci, Francesca Bianchini, Alessandro Contini, Andrea Trabocchi
Summary: Asparagine endopeptidase, also known as legumain, is a pH-dependent cysteine protease that cleaves substrates after asparagine residues. Recent studies have found its involvement in neurological diseases like Alzheimer's disease. Researchers synthesized compounds with different substituents and discovered one with nanomolar-range inhibition potency.
BIOORGANIC & MEDICINAL CHEMISTRY
(2022)
Article
Biochemistry & Molecular Biology
Caterina Dallari, Riccardo Innocenti, Elena Lenci, Andrea Trabocchi, Francesco Saverio Pavone, Caterina Credi
Summary: This study presents the synthesis of novel bioorthogonal Raman reporter-labeled nanoparticles using a versatile and cost-effective method, and demonstrates their potential for various applications in biological analysis.
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2022)
Article
Chemistry, Organic
Dina Scarpi, Francesco Bagni, Cristina Faggi, Asier Carral-Menoyo, Enrique Gomez-Bengoa, Ernesto G. Occhiato
Summary: Six- and seven-membered ring-fused, functionalized cyclopentadienes can be obtained in moderate to excellent yields through a cascade process involving various reactions. Depending on the treatment of the crude reaction mixtures, different types of cyclopentadienes can be obtained.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Review
Chemistry, Organic
Elena Lenci, Andrea Trabocchi
Summary: In the past two decades, Diversity-Oriented Synthesis (DOS) has undergone significant changes, shifting from a focus on structural diversity to incorporating new approaches to enhance the biological outcomes of molecules. Chemoinformatics has played a crucial role in identifying unexplored biologically-relevant regions of chemical space and visualizing and predicting the structural diversity and complexity of compounds within DOS libraries.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Biochemistry & Molecular Biology
Riccardo Innocenti, Caterina Dallari, Elena Lenci, Francesco S. Pavone, Francesca Bianchini, Caterina Credi, Andrea Trabocchi
Summary: This paper reports the synthesis of a novel functionalized triazole-based RGD peptidomimetic and its covalent conjugation on pegylated gold nanostars. These highly stable nanoconstructs showed a multivalent effect in binding alpha vS3 integrin receptors and proved to inhibit M21 cell adhesion at 25 pM concentration. Targeted gold nanostars with peculiar surface plasmon resonance in the NIR transparent window may represent a promising agent for anticancer multi-modality treatments.
BIOORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Filomena Tedesco, Lorenzo Calugi, Elena Lenci, Andrea Trabocchi
Summary: This study successfully inhibited the ACE2/spike interaction of SARS-CoV-2 using a synthesized peptidomimetic. Additionally, the peptidomimetic showed inhibition of SARS-CoV-2 3CLPro main protease activity, suggesting its potential as a multitarget therapeutic for coronavirus infections.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Biochemistry & Molecular Biology
Sara Peri, Jessica Ruzzolini, Silvia Urciuoli, Giampaolo Versienti, Alessio Biagioni, Elena Andreucci, Silvia Peppicelli, Francesca Bianchini, Andrea Bottari, Lido Calorini, Chiara Nediani, Lucia Magnelli, Laura Papucci
Summary: Oleocanthal, a compound found in extra-virgin olive oil, has been found to exhibit anticancer properties and can inhibit the growth of gastric cancer cells. In addition, an extract enriched with oleocanthal has a synergistic effect when used in combination with chemotherapy drugs, potentially overcoming drug resistance in gastric cancer cells.
Article
Biochemistry & Molecular Biology
Silvia Peppicelli, Jessica Ruzzolini, Matteo Lulli, Alessio Biagioni, Francesca Bianchini, Adele Caldarella, Chiara Nediani, Elena Andreucci, Lido Calorini
Summary: This study found a correlation between the epithelial-to-mesenchymal transition (EMT) of melanoma cells and the expression of estrogen receptor beta (ERβ). Extracellular acidosis induced an enhanced expression of ERβ in female cells, while not inducing its expression in male cells, and promoted EMT. ERβ was also found to regulate EMT through NF-kappa B activation.
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2022)
Article
Biochemistry & Molecular Biology
Elena Andreucci, Kelly Bugatti, Silvia Peppicelli, Jessica Ruzzolini, Matteo Lulli, Lido Calorini, Lucia Battistini, Franca Zanardi, Andrea Sartori, Francesca Bianchini
Summary: Growth factors and cytokines in the lung cancer microenvironment induce EMT and promote tumor progression. A novel conjugate targeting the α v β 6 integrin receptor, linked to the kinase inhibitor nintedanib, inhibits cancer cell adhesion and growth through selective delivery. The conjugate also suppresses clonogenic ability and other aspects associated with EMT transition, offering a precise strategy against non-small cell lung cancer.
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2023)
Article
Chemistry, Medicinal
Lorenzo Calugi, Giulia Sautariello, Elena Lenci, Mauro Leucio Mattei, Crescenzo Coppa, Nicoletta Cini, Alessandro Contini, Andrea Trabocchi
Summary: The design and synthesis of peptide derivatives based on an ACE2 alpha-helix 1 epitope and subsequent stapling of the secondary structure resulted in the identification of a 9-mer peptide capable of competing with recombinant ACE2 towards Spike RBD. The cyclization method was found to better stabilize the helical structure of the peptide epitope compared to the triazole stapling via click chemistry. Molecular dynamics simulations showed that the stapled peptide not only bound to Spike RBD and sterically interfered with ACE2, but also exhibited higher affinity to the target than the parent epitope.
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
(2023)
Article
Chemistry, Organic
Dina Scarpi, Nunzia Favale, Ernesto G. Occhiato
Summary: A highly efficient method for the one-pot synthesis of ring-fused 5-hydrazino-2-cyclopentenone derivatives is achieved through the catalysis of gold(I). Suitable enynyl acetates are mixed with a dialkylazodicarboxylate in the presence of a gold(I) catalyst to undergo cycloisomerization, hetero-Diels-Alder, and ring-opening reactions, resulting in the target compounds.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Medicinal
Vincenzo Maria D'Amore, Greta Donati, Elena Lenci, Beatrice Stefanie Ludwig, Susanne Kossatz, Monica Baiula, Andrea Trabocchi, Horst Kessler, Francesco Saverio Di Leva, Luciana Marinelli
Summary: In this study, the binding affinity of the peptide iRGD with cancer-related integrins, including αvβ3, αvβ5, and αvβ6, was re-evaluated. The conformation of iRGD in solution and its binding mechanism to integrin partners were investigated through simulations and calculations. Suggestions for improving its tumor-homing properties were provided.
JOURNAL OF CHEMICAL INFORMATION AND MODELING
(2023)
