Breaking the limits in glycan recognition by NMR

Publications

The Plasticity of the Carbohydrate Recognition Domain Dictates the Exquisite Mechanism of Binding of Human Macrophage Galactose-Type Lectin

Auteurs: Ana Diniz; Helena Coelho; Helena Coelho; Jorge S. Dias; Sandra J. van Vliet; Jesús Jiménez-Barbero; Jesús Jiménez-Barbero; Francisco Corzana; Eurico J. Cabrita; Filipa Marcelo
Publié dans: Chemistry A European Journal, Numéro 5, 2019, ISSN 0947-6539
Éditeur: John Wiley & Sons Ltd.
DOI: 10.1002/chem.201902780

Synthetic Zwitterionic <i>Streptococcus pneumoniae</i> Type 1 Oligosaccharides Carrying Labile <i>O</i> ‐Acetyl Esters

Auteurs: Zhen Wang; Ana Gimeno; Marta G. Lete; Herman S. Overkleeft; Gijsbert A. van der Marel; Fabrizio Chiodo; Jesús Jiménez‐Barbero; Jeroen D. C. Codée
Publié dans: Angewandte Chemie (International Edition), 2022, ISSN 1433-7851
Éditeur: John Wiley & Sons Ltd.
DOI: 10.1002/ange.202211940

Hypoxia reduces cell attachment of SARS-CoV-2 spike protein by modulating the expression of ACE2, neuropilin-1, syndecan-1 and cellular heparan sulfate

Auteurs: Endika Prieto-Fernández, Leire Egia-Mendikute, Laura Vila-Vecilla, Alexandre Bosch, Adrián Barreira-Manrique, So Young Lee, Ana García-Del Río, Asier Antoñana-Vildosola, Borja Jiménez-Lasheras, Leire Moreno-Cugnon, Jesús Jiménez-Barbero, Edurne Berra, June Ereño-Orbea, Asis Palazon.
Publié dans: Emerging Microbes & Infections, 2021, ISSN 2222-1751
Éditeur: Nature Publishing Group
DOI: 10.1080/22221751.2021.1932607

Synthetic, Zwitterionic Sp1 Oligosaccharides Adopt a Helical Structure Crucial for Antibody Interaction

Auteurs: Qingju Zhang, Ana Gimeno, Darielys Santana, Zhen Wang, Yury Valdés-Balbin, Laura M. Rodríguez-Noda, Thomas Hansen, Li Kong, Mengjie Shen, Herman S. Overkleeft, Vicente Vérez-Bencomo, Gijsbert A. van der Marel, Jesús Jiménez-Barbero, Fabrizio Chiodo, Jeroen D. C. Codée
Publié dans: ACS Central Science, Numéro 5/8, 2019, Page(s) 1407-1416, ISSN 2374-7943
Éditeur: American Chemistry Society
DOI: 10.1021/acscentsci.9b00454

Atomic and Specificity Details of Mucin 1 O-Glycosylation Process by Multiple Polypeptide GalNAc-Transferase Isoforms Unveiled by NMR and Molecular Modeling

Auteurs: Coelho, Helena; de las Rivas, Matilde; Grosso, Ana S.; Diniz, Ana; Soares, Catia O.; Francisco, Rodrigo A.; Dias, Jorge S.; Companon, Ismael; Sun, Lingbo; Narimatsu, Yoshiki; Vakhrushev, Sergey Y.; Clausen, Henrik; Cabrita, Eurico J.; Jimenez-Barbero, Jesus; Corzana, Francisco; Hurtado-Guerrero, Ramon; Marcelo, Filipa; 0000-0003-1992-8557; 0000-0001-5324-4998; 0000-0002-9102-3018; 0000-0001-9725-1
Publié dans: Journal of American Chemical Society, Numéro 12, 2022, ISSN 0002-7863
Éditeur: American Chemical Society
DOI: 10.1021/jacsau.1c00529

Assessing the Mobility of Severe Acute Respiratory Syndrome Coronavirus-2 Spike Protein Glycans by Structural and Computational Methods

Auteurs: Soledad Stagnoli; Francesca Peccati; Sean R. Connell; Ane Martinez-Castillo; Diego Charro; Oscar Millet; Chiara Bruzzone; Asis Palazon; Ana Ardá; Jesús Jiménez-Barbero; June Ereño-Orbea; Nicola G. A. Abrescia; Gonzalo Jiménez-Osés
Publié dans: Frontiers in Microbiology, Numéro 7, 2022, ISSN 1664-302X
Éditeur: Frontiers Media
DOI: 10.3389/fmicb.2022.870938

An Epoxide Intermediate in Glycosidase Catalysis

Auteurs: Lukasz F. Sobala, Gaetano Speciale, Sha Zhu, Lluıs Raich, Natalia Sannikova, Andrew J. Thompson, Zalihe Hakki, Dan Lu, Saeideh Shamsi Kazem Abadi, Andrew R. Lewis, Vıctor Rojas-Cervellera, ́ Ganeko Bernardo-Seisdedos, Yongmin Zhang, Oscar Millet, Jesus Jiménez-Barbero, Andrew J. Bennet, ́ Matthieu Sollogoub, Carme Rovira, Gideon J. Davies, and Spencer J. Williams
Publié dans: ACS Central Science, 2020, ISSN 2374-7951
Éditeur: American Chemical Society
DOI: 10.1021/acscentsci.0c00111

The SARS-CoV-2 Spike Glycoprotein Directly Binds Exogeneous Sialic Acids: A NMR View

Auteurs: Luca Unione; María J. Moure; Maria Pia Lenza; Iker Oyenarte; June Ereño‐Orbea; Ana Ardá; Jesús Jiménez‐Barbero
Publié dans: Angewandte Chemie International Edition, Numéro 2, 2022, ISSN 1433-7851
Éditeur: John Wiley & Sons Ltd.
DOI: 10.1002/ange.202201432

Galectin-4 N-Terminal Domain: Binding Preferences Toward A and B Antigens With Different Peripheral Core Presentations

Auteurs: Jon I. Quintana, Sandra Delgado, Reyes Núñez-Franco, F. Javier Cañada, Gonzalo Jiménez-Osés, Jesús Jiménez-Barbero, Ana Ardá
Publié dans: Frontiers in Chemistry, Numéro 9, 2021, ISSN 2296-2646
Éditeur: Frontiers Media SA
DOI: 10.3389/fchem.2021.664097

Fluorinated Carbohydrates as Lectin Ligands: Simultaneous Screening of a Monosaccharide Library and Chemical Mapping by 19 F NMR Spectroscopy

Auteurs: J. Daniel Martínez, Ana I. Manzano, Eva Calviño, Ana de Diego, Borja Rodriguez de Francisco, Cecilia Romanò, Stefan Oscarson, Oscar Millet, Hans-Joachim Gabius, Jesús Jiménez-Barbero, Francisco J. Cañada
Publié dans: The Journal of Organic Chemistry, Numéro 85/24, 2020, Page(s) 16072-16081, ISSN 0022-3263
Éditeur: American Chemical Society
DOI: 10.1021/acs.joc.0c01830

Novel NMR Avenues to Explore the Conformation and Interactions of Glycans

Auteurs: Pablo Valverde, Jon I. Quintana, Jose I. Santos, Ana Ardá, Jesús Jiménez-Barbero
Publié dans: ACS Omega, Numéro 4/9, 2019, Page(s) 13618-13630, ISSN 2470-1343
Éditeur: American Chemical Society
DOI: 10.1021/acsomega.9b01901

Targeting Galectins With Glycomimetics

Auteurs: Sara Bertuzzi, Jon I. Quintana, Ana Ardá, Ana Gimeno, Jesús Jiménez-Barbero
Publié dans: Frontiers in Chemistry, Numéro 8, 2020, ISSN 2296-2646
Éditeur: Frontiers Media
DOI: 10.3389/fchem.2020.00593

Cross-Linking Effects Dictate the Preference of Galectins to Bind LacNAc-Decorated HPMA Copolymers

Auteurs: Sara Bertuzzi, Ana Gimeno, Ane Martinez-Castillo, Marta G. Lete, Sandra Delgado, Cristina Airoldi, Marina Rodrigues Tavares, Markéta Bláhová, Petr Chytil, Vladimír Křen, Nicola G. A. Abrescia, Ana Ardá, Pavla Bojarová, Jesús Jiménez-Barbero
Publié dans: International Journal of Molecular Sciences, Numéro 22/11, 2021, Page(s) 6000, ISSN 1422-0067
Éditeur: Multidisciplinary Digital Publishing Institute (MDPI)
DOI: 10.3390/ijms22116000

Unravelling the Time Scale of Conformational Plasticity and Allostery in Glycan Recognition by Human Galectin‐1

Auteurs: Sara Bertuzzi, Ana Gimeno, Reyes Núñez‐Franco, Ganeko Bernardo‐Seisdedos, Sandra Delgado, Gonzalo Jiménez‐Osés, Oscar Millet, Jesús Jiménez‐Barbero, Ana Ardá
Publié dans: Chemistry – A European Journal, Numéro 26/67, 2020, Page(s) 15643-15653, ISSN 0947-6539
Éditeur: John Wiley & Sons Ltd.
DOI: 10.1002/chem.202003212

The two domains of human galectin-8 bind sialyl- and fucose-containing oligosaccharides in an independent manner. A 3D view by using NMR

Auteurs: Marcos Gómez-Redondo, Sandra Delgado, Reyes Núñez-Franco, Gonzalo Jiménez-Osés, Ana Ardá, Jesús Jiménez-Barbero, Ana Gimeno
Publié dans: RSC Chemical Biology, Numéro 2/3, 2021, Page(s) 932-941, ISSN 2633-0679
Éditeur: RSC
DOI: 10.1039/d1cb00051a

Calorimetric Studies of Binary and Ternary Molecular Interactions between Transthyretin, Aβ Peptides, and Small-Molecule Chaperones toward an Alternative Strategy for Alzheimer's Disease Drug Discovery.

Auteurs: Ellen Y. Cotrina; Ana Gimeno; Jordi Llop; Jesús Jiménez-Barbero; Jesús Jiménez-Barbero; Jordi Quintana; Gregorio Valencia; Isabel Cardoso; Isabel Cardoso; Rafel Prohens; Gemma Arsequell
Publié dans: Journal of Medicinal Chemistry, Numéro 3, 2020, ISSN 0022-2623
Éditeur: American Chemical Society
DOI: 10.1021/acs.jmedchem.9b01970

Synthesis and Structural Analysis of Aspergillus fumigatus Galactosaminogalactans Featuring α-Galactose, α-Galactosamine and α-N-Acetyl Galactosamine Linkages

Auteurs: Yongzhen Zhang; Marcos Gómez-Redondo; Gonzalo Jiménez-Osés; Ana Ardá; Herman S. Overkleeft; Gijsbert A. van der Marel; Jesús Jiménez-Barbero; Jeroen D. C. Codée
Publié dans: Angewandte Chemie International Edition, Numéro 7, 2020, ISSN 1433-7851
Éditeur: John Wiley & Sons Ltd.
DOI: 10.1002/ange.202003951

Molecular Recognition in C‐Type Lectins: The Cases of DC‐SIGN, Langerin, MGL, and L‐Sectin

Auteurs: Pablo Valverde, J. Daniel Martínez, F. Javier Cañada, Ana Ardá, Jesús Jiménez‐Barbero
Publié dans: ChemBioChem, Numéro 21/21, 2020, Page(s) 2999-3025, ISSN 1439-4227
Éditeur: John Wiley & Sons Ltd.
DOI: 10.1002/cbic.202000238

Glycosyl Oxocarbenium Ions: Structure, Conformation, Reactivity, and Interactions

Auteurs: Antonio Franconetti; Ana Ardá; Juan Luis Asensio; Yves Blériot; Sébastien Thibaudeau; Jesús Jiménez-Barbero; Jesús Jiménez-Barbero
Publié dans: Accounts of Chemical Research, Numéro 2, 2021, ISSN 0001-4842
Éditeur: American Chemical Society
DOI: 10.1021/acs.accounts.1c00021

Oligosaccharide Presentation Modulates the Molecular Recognition of Glycolipids by Galectins on Membrane Surfaces

Auteurs: Marta G. Lete; Antonio Franconetti; Sandra Delgado; Jesús Jiménez-Barbero; Ana Ardá
Publié dans: Pharmaceuticals, 2022, ISSN 1424-8247
Éditeur: Multidisciplinary Digital Publishing Institute (MDPI)
DOI: 10.3390/ph15020145

Fluorinated carbohydrates as chemical probes for molecular recognition studies. Current status and perspectives

Auteurs: Bruno Linclau, Ana Ardá, Niels-Christian Reichardt, Matthieu Sollogoub, Luca Unione, Stéphane P. Vincent, Jesús Jiménez-Barbero
Publié dans: Chemical Society Reviews, Numéro 49/12, 2020, Page(s) 3863-3888, ISSN 0306-0012
Éditeur: Royal Society of Chemistry
DOI: 10.1039/c9cs00099b

The Interaction of Fluorinated Glycomimetics with DC-SIGN: Multiple Binding Modes Disentangled by the Combination of NMR Methods and MD Simulations

Auteurs: J. Daniel Martínez, Angela S. Infantino, Pablo Valverde, Tammo Diercks, Sandra Delgado, Niels-Christian Reichardt, Ana Ardá, Francisco Javier Cañada, Stefan Oscarson, Jesús Jiménez-Barbero
Publié dans: Pharmaceuticals, Numéro 13/8, 2020, Page(s) 179, ISSN 1424-8247
Éditeur: Multidisciplinary Digital Publishing Institute (MDPI)
DOI: 10.3390/ph13080179

The Flexibility of Oligosaccharides Unveiled Through Residual Dipolar Coupling Analysis

Auteurs: Ana Poveda Giulio Fittolani Peter H. Seeberger Martina Delbianco and Jesús Jiménez-Barbero
Publié dans: Frontiers in Molecular Biosciences, 2021, ISSN 2296-889X
Éditeur: Frontiers Media
DOI: 10.3389/fmolb.2021.784318

Immobilization of Biantennary N-Glycans Leads to Branch Specific Epitope Recognition by LSECtin.

Auteurs: Bertuzzi, Sara; Peccati, Francesca; Serna, Sonia; Artschwager, Raik; Notova, Simona; Thépaut, Michel; Jiménez-Osés, Gonzalo; Fieschi, Franck; Reichardt, Niels C.; Jiménez-Barbero, Jesús; Ardá, Ana; 0000-0002-4242-7067; 0000-0003-0105-4337; 0000-0001-5421-8513; 0000-0003-3027-7417
Publié dans: ACS Central Science, Numéro 2, 2022, ISSN 2374-7951
Éditeur: American Chemical Society
DOI: 10.1021/acscentsci.2c00719

NMR Investigation of Protein-Carbohydrate Interactions: The Recognition of Glycans by Galectins Engineered with Fluorotryptophan Residues

Auteurs: Lete, Marta G.; Franconetti, Antonio; Bertuzzi, Sara; Delgado, Sandra; Azkargorta, Mikel; Elortza, Félix; Millet, Oscar; Jiménez-Osés, Gonzalo; Arda, Ana; Jiménez-Barbero, Jesús; 0000-0002-9654-7881; 0000-0002-7972-8795; 0000-0002-4242-7067; 0000-0001-5848-6590; 0000-0001-8839-5438; 0000-0001-8748-4105; 0000-0003-0105-4337; 0000-0003-3027-7417; 0000-0001-5421-8513
Publié dans: Chemistry An European Journal, 2023, ISSN 0947-6539
Éditeur: John Wiley & Sons Ltd.
DOI: 10.1002/chem.202202208

Molecular Insights into DC-SIGN Binding to Self-Antigens: The Interaction with the Blood Group A/B Antigens

Auteurs: Pablo Valverde, Sandra Delgado, J. Daniel Martínez, Jean-Baptiste Vendeville, Julien Malassis, Bruno Linclau, Niels-Christian Reichardt, Francisco Javier Cañada, Jesús Jiménez-Barbero, Ana Ardá
Publié dans: ACS Chemical Biology, Numéro 14/7, 2019, Page(s) 1660-1671, ISSN 1554-8929
Éditeur: American Chemical Society
DOI: 10.1021/acschembio.9b00458

Unraveling Sugar Binding Modes to DC-SIGN by Employing Fluorinated Carbohydrates

Auteurs: J. Daniel Martínez, Pablo Valverde, Sandra Delgado, Cecilia Romanò, Bruno Linclau, Niels C. Reichardt, Stefan Oscarson, Ana Ardá, Jesús Jiménez-Barbero, F. Javier Cañada
Publié dans: Molecules, Numéro 24/12, 2019, Page(s) 2337, ISSN 1420-3049
Éditeur: Multidisciplinary Digital Publishing Institute (MDPI)
DOI: 10.3390/molecules24122337

Glycan structures and their interactions with proteins. A NMR view

Auteurs: Ana Gimeno, Pablo Valverde, Ana Ardá, Jesús Jiménez-Barbero
Publié dans: Current Opinion in Structural Biology, Numéro 62, 2020, Page(s) 22-30, ISSN 0959-440X
Éditeur: Elsevier BV
DOI: 10.1016/j.sbi.2019.11.004

Minimizing the Entropy Penalty for Ligand Binding: Lessons from the Molecular Recognition of the Histo Blood‐Group Antigens by Human Galectin‐3

Auteurs: Ana Gimeno, Sandra Delgado, Pablo Valverde, Sara Bertuzzi, Manuel Alvaro Berbís, Javier Echavarren, Alessandra Lacetera, Sonsoles Martín‐Santamaría, Avadhesha Surolia, Francisco Javier Cañada, Jesus Jiménez‐Barbero, Ana Ardá
Publié dans: Angewandte Chemie International Edition, Numéro 58/22, 2019, Page(s) 7268-7272, ISSN 1433-7851
Éditeur: John Wiley & Sons Ltd.
DOI: 10.1002/anie.201900723

Avenues to Characterize the Interactions of Extended N‐Glycans with Proteins by NMR Spectroscopy: The Influenza Hemagglutinin Case

Auteurs: Beatriz Fernández de Toro, Wenjie Peng, Andrew J. Thompson, Gema Domínguez, F. Javier Cañada, Javier Pérez‐Castells, James C. Paulson, Jesús Jiménez‐Barbero, Ángeles Canales
Publié dans: Angewandte Chemie International Edition, Numéro 57/46, 2018, Page(s) 15051-15055, ISSN 1433-7851
Éditeur: John Wiley & Sons Ltd.
DOI: 10.1002/anie.201807162

Glycans in drug discovery

Auteurs: Pablo Valverde, Ana Ardá, Niels-Christian Reichardt, Jesús Jiménez-Barbero, Ana Gimeno
Publié dans: MedChemComm, Numéro 10/10, 2019, Page(s) 1678-1691, ISSN 2040-2503
Éditeur: Royal Society of Chemistry
DOI: 10.1039/c9md00292h

Synthesis, Conformational Analysis, and Complexation Study of an Iminosugar-Aza-Crown, a Sweet Chiral Cyclam Analog

Auteurs: Alexandra Bordes, Ana Poveda, Thibault Troadec, Antonio Franconetti, Ana Ardá, Flavie Perrin, Mickaël Ménand, Matthieu Sollogoub, Jerôme Guillard, Jérôme Désiré, Raphaël Tripier, Jesús Jiménez-Barbero, Yves Blériot
Publié dans: Organic Letters, Numéro 22/6, 2020, Page(s) 2344-2349, ISSN 1523-7060
Éditeur: American Chemical Society
DOI: 10.1021/acs.orglett.0c00503

Structural Characterization of N‐Linked Glycans in the Receptor Binding Domain of the SARS‐CoV‐2 Spike Protein and their Interactions with Human Lectins

Auteurs: Maria Pia Lenza, Iker Oyenarte, Tammo Diercks, Jon Imanol Quintana, Ana Gimeno, Helena Coelho, Ana Diniz, Francesca Peccati, Sandra Delgado, Alexandre Bosch, Mikel Valle, Oscar Millet, Nicola G. A. Abrescia, Asís Palazón, Filipa Marcelo, Gonzalo Jiménez‐Osés, Jesús Jiménez‐Barbero, Ana Ardá, June Ereño‐Orbea
Publié dans: Angewandte Chemie International Edition, Numéro 59/52, 2020, Page(s) 23763-23771, ISSN 1433-7851
Éditeur: John Wiley & Sons Ltd.
DOI: 10.1002/anie.202011015

Current Status on Therapeutic Molecules Targeting Siglec Receptors

Auteurs: María Pia Lenza, Unai Atxabal, Iker Oyenarte, Jesús Jiménez-Barbero, June Ereño-Orbea
Publié dans: Cells, Numéro 9/12, 2020, Page(s) 2691, ISSN 2073-4409
Éditeur: MDPI
DOI: 10.3390/cells9122691

Structures of the Inhibitory Receptor Siglec‑8 in Complex with a High-Affinity Sialoside Analogue and a Therapeutic Antibody

Auteurs: Lenza, Maria Pia; Atxabal, Unai; Nycholat, Corwin; Oyenarte, Iker; Franconetti, Antonio; Quintana, Jon Imanol; Delgado, Sandra; Núñez-Franco, Reyes; Garnica Marroquín, Carmen Teresa; Coelho, Helena; Unione, Luca; Jiménez-Oses, Gonzalo; Marcelo, Filipa; Schubert, Mario; Paulson, James C.; Jiménez-Barbero, Jesús; Ereño-Orbea, June; 0000-0002-7972-8795; 0000-0003-1992-8557; 0000-0003-0105-4337
Publié dans: JACS Au, Numéro 9, 2022, ISSN 2691-3704
Éditeur: American Chemical Society
DOI: 10.1021/jacsau.2c00592

Glycoprofile Analysis of an Intact Glycoprotein As Inferred by NMR Spectroscopy

Auteurs: Luca Unione, Maria Pia Lenza, Ana Ardá, Pedro Urquiza, Ana Laín, Juan Manuel Falcón-Pérez, Jesús Jiménez-Barbero, Oscar Millet
Publié dans: ACS Central Science, Numéro 5/9, 2019, Page(s) 1554-1561, ISSN 2374-7943
Éditeur: American Chemical Society
DOI: 10.1021/acscentsci.9b00540

Selective 13 C‐Labels on Repeating Glycan Oligomers to Reveal Protein Binding Epitopes through NMR: Polylactosamine Binding to Galectins

Auteurs: María J. Moure, Ana Gimeno, Sandra Delgado, Tammo Diercks, Geert‐Jan Boons, Jesús Jiménez‐Barbero, Ana Ardá
Publié dans: Angewandte Chemie International Edition, Numéro 60/34, 2021, Page(s) 18777-18782, ISSN 1433-7851
Éditeur: John Wiley & Sons Ltd.
DOI: 10.1002/anie.202106056

Mono‐ and Di‐Fucosylated Glycans of the Parasitic Worm S. mansoni are Recognized Differently by the Innate Immune Receptor DC‐SIGN

Auteurs: Apoorva D. Srivastava, Luca Unione, Margreet A. Wolfert, Pablo Valverde, Ana Ardá, Jesús Jiménez‐Barbero, Geert‐Jan Boons
Publié dans: Chemistry – A European Journal, Numéro 26/67, 2020, Page(s) 15605-15612, ISSN 0947-6539
Éditeur: John Wiley & Sons Ltd.
DOI: 10.1002/chem.202002619

Structure-Guided Design of a Group B Streptococcus Type IIISynthetic Glycan–Conjugate Vaccine

Auteurs: Davide Oldrini, Linda del Bino, Ana Arda, Filippo Carboni,[a] Pedro Henriques,Francesca Angiolini, Jon I. Quintana, Ilaria Calloni, Maria R. Romano, Francesco Berti, Jesus Jimenez-Barbero, Immaculada Margarit, and Roberto Adamo
Publié dans: Chemistry A European Journal, 2020, ISSN 0947-6539
Éditeur: John Wiley & Sons Ltd.
DOI: 10.1002/chem.202000284

Exploring multivalent carbohydrate–protein interactions by NMR

Auteurs: Jon I. Quintana; Unai Atxabal; Luca Unione; Ana Ardá; Jesús Jiménez-Barbero
Publié dans: Crossref, Numéro 1, 2023, ISSN 0306-0012
Éditeur: Royal Society of Chemistry
DOI: 10.1039/d2cs00983h

Kinetic Studies of Acetyl Group Migration between the Saccharide Units in an Oligomannoside Trisaccharide Model Compound and a Native Galactoglucomannan Polysaccharide

Auteurs: Robert Lassfolk, Sara Bertuzzi, Ana Ardá, Johan Wärnå, Jesús Jiménez‐Barbero, Reko Leino
Publié dans: ChemBioChem, Numéro 22/20, 2021, Page(s) 2986-2995, ISSN 1439-4227
Éditeur: John Wiley & Sons Ltd.
DOI: 10.1002/cbic.202100374

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