Article
Chemistry, Medicinal
Rita Goncalves-Pereira, Jose A. Figueiredo, Susana D. Lucas, Maria I. Garcia-Moreno, Carmen O. Mellet, Amelia P. Rauter, Maria I. Ismael
Summary: Alzheimer's disease is a multifactorial syndrome that causes memory loss, dementia, and eventually death. Acetylcholinesterase inhibitors are the main drugs used for symptomatic treatment of the disease. This study reports a new synthetic route for producing sugar amides that act as acetylcholinesterase inhibitors.
MEDICINAL CHEMISTRY
(2023)
Review
Chemistry, Multidisciplinary
Ignacio Sanz-Martinez, Sandra Pereira, Pedro Merino, Francisco Corzana, Ramon Hurtado-Guerrero
Summary: N-acetylgalactosamine (GalNAc) type O-glycosylation is a crucial posttranslational modification in biology. Malfunction of this modification is associated with truncated O-glycans in cancer. Understanding the structure and recognition of GalNAc-containing glycopeptides can contribute to the development of therapeutic vaccines and new diagnostic tools for cancer detection.
ACCOUNTS OF CHEMICAL RESEARCH
(2023)
Article
Chemistry, Medicinal
Manuel Gonzalez-Cuesta, Alan Chuan-Ying Lai, Po-Yu Chi, I-Ling Hsu, Nien-Tzu Liu, Ko-Chien Wu, Jose M. Garcia Fernandez, Ya-Jen Chang, Carmen Ortiz Mellet
Summary: Replacement of the sugar fragment with an sp(2)-iminosugar moiety in a TLR4 agonist yields iminoglycolipid analogues that retain or improve their biological activity in vitro and in vivo. These analogues have adjuvant potential by inducing proinflammatory cytokines secretion, promoting dendritic cells maturation, and CD8(+) T cells proliferation, with a Th1-biased profile. They also show therapeutic potential for the treatment of Th2-dominated inflammatory diseases such as asthma.
JOURNAL OF MEDICINAL CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Gean M. Dal Forno, Eloah Latocheski, Ana Beatriz Machado, Julie Becher, Lavinia Dunsmore, Albert L. St John, Bruno L. Oliveira, Claudio D. Navo, Gonzalo Jimenez-Oses, Rita Fior, Josiel B. Domingos, Goncalo J. L. Bernardes
Summary: The ability to control prodrug activation by transition metals has great potential for controlled drug release in cancer cells. However, current strategies are limited to cleavage of C-O or C-N bonds, hindering the use of drugs with amino or hydroxyl groups. This study presents a palladium-mediated C-C bond cleavage method for the activation of an ortho-quinone prodrug, expanding the range of drugs that can be used.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Organic
Matteo A. . Tallarida, Fabrizio Olivito, Claudio D. Navo, Vincenzo Algieri, Antonio Jiritano, Paola Costanzo, Ana Poveda, Maria J. Moure, Jesus Jimenez-Barbero, Loredana Maiuolo, Gonzalo Jimenez-Oses, Antonio De Nino
Summary: The synthesis of polysubstituted spirocyclopropyl oxindoles using rare-earth metal (REM) salts, particularly Sc(OTf)3, was achieved with high diastereoselectivity (<= 94:6:0:0) in a multicomponent reaction. Density functional theory calculations on the model reaction confirmed the observed selectivity and demonstrated that the coordinating capabilities and oxophilicity of the metal played a crucial role in inducing the formation of one main diastereoisomer.
Article
Chemistry, Organic
Nuria Mazo, Imran R. Rahman, Claudio D. Navo, Jesus M. Peregrina, Jesus H. Busto, Wilfred A. . van der Donk, Gonzalo Jimenez-Oses
Summary: This study reports a common strategy for the synthesis of lanthionine derivatives using nucleophilic ring opening of cyclic sulfamidates derived from amino acids. The researchers achieved regio-, chemo-, and stereoselective intramolecular S-alkylation of a cysteine residue with N-sulfonyl sulfamidates for the synthesis of cyclic lanthionine-containing peptides. Four different analogues of cytolysin S (CylLS '') were successfully synthesized and their conformational preferences and biological activities were compared with wild-type CylLS ''.
Article
Multidisciplinary Sciences
Itxaso Anso, Andreas Naegeli, Javier O. Cifuente, Ane Orrantia, Erica Andersson, Olatz Zenarruzabeitia, Alicia Moraleda-Montoya, Mikel Garcia-Alija, Francisco Corzana, Rafael A. Del Orbe, Francisco Borrego, Beatriz Trastoy, Jonathan Sjogren, Marcelo E. Guerin
Summary: Red blood cell antigens are critical in blood transfusion. Researchers have discovered a bacterial enzyme called FucOB that can convert universal O type blood into the rare Bombay type blood. This finding has the potential to facilitate transfusion in recipients with the Bombay phenotype.
NATURE COMMUNICATIONS
(2023)
Article
Multidisciplinary Sciences
Maria Pia Lenza, Leire Egia-Mendikute, Asier Antonana-Vildosola, Catia O. Soares, Helena Coelho, Francisco Corzana, Alexandre Bosch, Prodhi Manisha, Jon Imanol Quintana, Iker Oyenarte, Luca Unione, Maria Jesus Moure, Mikel Azkargorta, Unai Atxabal, Klaudia Sobczak, Felix Elortza, James D. Sutherland, Rosa Barrio, Filipa Marcelo, Jesus Jimenez-Barbero, Asis Palazon, June Ereno-Orbea
Summary: This study elucidates the structure and binding epitope of Siglec-15, providing insights into its mechanism of action and potential for cancer immunotherapy. The findings highlight the importance of glycosylation in controlling T cell responses and identify CD11b as a binding partner for Siglec-15 on human T cells.
NATURE COMMUNICATIONS
(2023)
Article
Biochemistry & Molecular Biology
Elena Harjes, Patrick J. B. Edwards, Sean W. W. Bisset, Mark L. L. Patchett, Geoffrey B. B. Jameson, Sung-Hyun Yang, Claudio D. D. Navo, Paul W. R. Harris, Margaret A. A. Brimble, Gillian E. E. Norris
Summary: Glycocin F (GccF), secreted by Lactobacillus plantarum KW30, inhibits susceptible bacteria growth at nanomolar concentrations. A small chemical modification of Ser18, substituting the C-alpha proton with a methyl group, significantly reduces the antimicrobial activity of GccF. The comparison of the NMR structures of GccF(alpha-methylSer18) and native GccF reveals differences in loop conformation, dynamics, and glycan presentation, suggesting their importance in the interaction of GccF with essential physiological target molecules.
Article
Chemistry, Multidisciplinary
Irene Herrera-Gonzalez, Manuel Gonzalez-Cuesta, Michel Thepaut, Eugenie Laigre, David Goyard, Javier Rojo, Jose M. Garcia Fernandez, Franck Fieschi, Olivier Renaudet, Pedro M. Nieto, Carmen Ortiz Mellet
Summary: The carbohydrate chemical mimicry of sp2-iminosugars enables the synthesis of high-mannose-type oligosaccharide analogs whose solution and lectin bound conformations match those of the natural partners. The ability to finely modulate the binding affinity and selectivity towards specific lectins by incorporating the OMJ sp2-iminosugar caps offers potential applications in various fields.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Organic
Marina Carranza, Ana T. Carmona, Claudio D. Navo, Inmaculada Robina, Simone Fratta, Carlos Newburn, Gonzalo Jimenez-Oses, Antonio J. Moreno-Vargas
Summary: 2-Halo-3-tosyl-oxanorbornadienes can accept two thiol molecules to form isolable oxabicyclic thiovinyl sulfones, and then react with a second thiol molecule. The substitution pattern of the oxanorbornadienic skeleton influences the reaction rate through electronic and steric factors.
Article
Multidisciplinary Sciences
Beatriz Piniello, Javier Macias-Leon, Shun Miyazaki, Ana Garcia-Garcia, Ismael Companon, Mattia Ghirardello, Victor Taleb, Billy Veloz, Francisco Corzana, Atsushi Miyagawa, Carme Rovira, Ramon Hurtado-Guerrero
Summary: In this study, the structures of soluble HMW1C-like N-glycosyltransferases (NGTs) were reported, revealing a key dyad of basic/acidic residues that plays a crucial role in Asn catalysis. The study also found that UDP-galactose and UDP-glucose mimetics act as poor substrates and inhibitors, impeding catalysis. QM/MM simulations provide insight into the reaction mechanism of AaNGT. These findings are important for understanding the mechanism of NGTs and designing drugs.
NATURE COMMUNICATIONS
(2023)
Article
Chemistry, Organic
Faiza Diaba, Gisela Trenchs
Summary: The first violet light-mediated synthesis of gamma- and delta-lactams from N-alkenyl trichloroacetamides is reported in this paper. The reactions are conducted in tetrahydrofuran or 2-methyltetrahydrofuran as the sole solvent without catalysts or additives, under non-anhydrous conditions in an air atmosphere where the solvent serves as the radical initiator.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Feroze Hussain, Sajjad Ahmed, Ashiq Hussain Padder, Qazi Naveed Ahmed
Summary: This study reports a novel and efficient one-pot synthesis method for mixed phosphorotrithioates, which does not require supplementary additives and shows broad applicability.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Hyunjin Oh, Ikyon Kim
Summary: A new 1,2,4-triazole-pyrrolo[1,2-a]pyrazine hybrid system, 6-acylpyrrolo[1,2-a][1,2,4]triazolo[5,1-c]pyrazine, was synthesized using a catalyst-free method. This method involved sequential exposure of pyrrole-2-carbonitrile-derived substrates to DMF-DMA and acyl hydrazide, resulting in the formation of acylated pyrazine and 1,2,4-triazole rings, enabling the installation of various substituents at specific positions on the core skeleton.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Ming Yan, Si-fan Wang, Yong-po Zhang, Jin-zhong Zhao, Zhuo Tang, Guang-xun Li
Summary: Here we developed an efficient photocatalytic approach for the convenient preparation of sulfinamides. The reaction allows for the gram-scale preparation of sulfinamides and the one-pot synthesis of various sulfonyl amides.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Farzaneh Bandehali-Naeini, Zahra Tanbakouchian, Noushin Farajinia-Lehi, Nicolas Mayer, Morteza Shiri, Martin Breugst
Summary: Two tandem catalytic systems were developed for the synthesis of novel 3,4-disubstituted maleimides using the same Ugi adducts. Different maleimide structures can be synthesized using either Pd or Cu catalysis.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Tanya Raghava, Anjan Chattopadhyay, Subhadeep Banerjee, Nivedita Sarkar
Summary: Amine substitution of two ortho fluorine atoms of tetrafluoroterephthalonitrile through SNAr chemistry is easily achievable. But further fluorine substitution is only possible under forcing conditions, yielding valuable fluorophores for bioimaging.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Review
Chemistry, Organic
Anju Chadha, Santosh Kumar Padhi, Selvaraj Stella, Sowmyalakshmi Venkataraman, Thangavelu Saravanan
Summary: Alcohol dehydrogenases are enzymes that use cofactors for oxidation or reduction reactions of alcohols or carbonyl compounds. They are utilized in green chemistry and have applications in the production of pharmaceuticals. Recombinant enzymes have solved the challenge of producing purified enzymes in large quantities. Engineered alcohol dehydrogenases have been used in asymmetric synthesis in industry. Various methods have been established for regenerating expensive cofactors to make the enzymatic process more efficient and economically viable.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
