title: Tn Antigen Mimics Based on sp(2)-Iminosugars with Affinity for an anti-MUC1 Antibody.
abstract: The first examples of amino acid (Ser/Thr)-sp(2)-iminosugar glycomimetic conjugates featuring an α-O-linked pseudoanomeric linkage are reported. The key synthetic step involves the completely diastereoselective α-glycosylation of Ser/Thr due to strong stereoelectronic and conformational bias imposed by the bicyclic sp(2)-iminosugar scaffold. Mucin-related glycopeptides incorporating these motifs were recognized by the monoclonal antibody (mAb) scFv-SM3, with activities depending on both the hydroxylation pattern (Glc/Gal/GlcNAc/GalNAc) of the sp(2)-iminosugar and the peptide aglycone structure (Ser/Thr).
authors.affiliation: Dept. Química Orgánica, Facultad de Química, Universidad de Sevilla , E-41012 Sevilla, Spain.
authors.forename: Elena M Sánchez
authors.initials: EM
authors.lastname: Fernández
authors.affiliation: Dept. Química, Universidad de La Rioja, Centro de Investigación en Síntesis Química , E-26006 Logroño, Spain.
authors.forename: Claudio D
authors.initials: CD
authors.lastname: Navo
authors.affiliation: Department of Chemistry, University of Cambridge , Lensfield Road, Cambridge CB2 1EW, U.K.
authors.forename: Nuria
authors.initials: N
authors.lastname: Martínez-Sáez
authors.affiliation: Dept. Química Orgánica, Facultad de Química, Universidad de Sevilla , E-41012 Sevilla, Spain.
authors.forename: Rita
authors.initials: R
authors.lastname: Gonçalves-Pereira
authors.affiliation: Department of Chemistry, University of Cambridge , Lensfield Road, Cambridge CB2 1EW, U.K.
authors.forename: Víctor J
authors.initials: VJ
authors.lastname: Somovilla
authors.affiliation: Dept. Química, Universidad de La Rioja, Centro de Investigación en Síntesis Química , E-26006 Logroño, Spain.
authors.forename: Alberto
authors.initials: A
authors.lastname: Avenoza
authors.affiliation: Dept. Química, Universidad de La Rioja, Centro de Investigación en Síntesis Química , E-26006 Logroño, Spain.
authors.forename: Jesús H
authors.initials: JH
authors.lastname: Busto
authors.affiliation: Department of Chemistry, University of Cambridge , Lensfield Road, Cambridge CB2 1EW, U.K.|Instituto de Medicina Molecular, Faculdade de Medicina, Universidade de Lisboa , Avenida Professor Egas Moniz, 1649-028, Lisboa, Portugal.
authors.forename: Gonçalo J L
authors.initials: GJ
authors.lastname: Bernardes
authors.affiliation: Dept. Química, Universidad de La Rioja, Centro de Investigación en Síntesis Química , E-26006 Logroño, Spain.|Institute of Biocomputation and Physics of Complex Systems (BIFI), University of Zaragoza, BIFI-IQFR (CSIC) , Zaragoza, Spain.
authors.forename: Gonzalo
authors.initials: G
authors.lastname: Jiménez-Osés
authors.affiliation: Dept. Química, Universidad de La Rioja, Centro de Investigación en Síntesis Química , E-26006 Logroño, Spain.
authors.forename: Francisco
authors.initials: F
authors.lastname: Corzana
authors.affiliation: Instituto de Investigaciones Químicas (IIQ), CSIC-Universidad de Sevilla , E-41092 Sevilla, Spain.
authors.forename: José M García
authors.initials: JM
authors.lastname: Fernández
authors.affiliation: Dept. Química Orgánica, Facultad de Química, Universidad de Sevilla , E-41012 Sevilla, Spain.
authors.forename: Carmen Ortiz
authors.initials: CO
authors.lastname: Mellet
authors.affiliation: Dept. Química, Universidad de La Rioja, Centro de Investigación en Síntesis Química , E-26006 Logroño, Spain.
authors.forename: Jesús M
authors.initials: JM
authors.lastname: Peregrina
mesh_terms: D000596:Amino Acids / Q000737:chemistry* / Q000276:immunology*; D000911:Antibodies, Monoclonal / Q000276:immunology*; D000915:Antibody Affinity; D015295:Antigens, Tumor-Associated, Carbohydrate / Q000737:chemistry*; D006020:Glycopeptides / Q000737:chemistry / Q000276:immunology; D006801:Humans; D018396:Mucin-1 / Q000276:immunology*
chemical_list: D000596:Amino Acids; D000911:Antibodies, Monoclonal; D015295:Antigens, Tumor-Associated, Carbohydrate; D006020:Glycopeptides; C060192:MUC1 protein, human; D018396:Mucin-1; C040286:Tn antigen