title: Serine versus threonine glycosylation with α-O-GalNAc: unexpected selectivity in their molecular recognition with lectins.
abstract: The molecular recognition of several glycopeptides bearing Tn antigen (α-O-GalNAc-Ser or α-O-GalNAc-Thr) in their structure by three lectins with affinity for this determinant has been analysed. The work yields remarkable results in terms of epitope recognition, showing that the underlying amino acid of Tn (serine or threonine) plays a key role in the molecular recognition. In fact, while Soybean agglutinin and Vicia villosa agglutinin lectins prefer Tn-threonine, Helix pomatia agglutinin shows a higher affinity for the glycopeptides carrying Tn-serine. The different conformational behaviour of the two Tn biological entities, the residues of the studied glycopeptides in the close proximity to the Tn antigen and the topology of the binding site of the lectins are at the origin of these differences.
authors.affiliation: Departamento de Química, Centro de investigación en Síntesis Química, Universidad de La Rioja, C/Madre de Dios 51, 26006 Logroño (Spain).
authors.forename: David
authors.initials: D
authors.lastname: Madariaga
authors.forename: Nuria
authors.initials: N
authors.lastname: Martínez-Sáez
authors.forename: Víctor J
authors.initials: VJ
authors.lastname: Somovilla
authors.forename: Laura
authors.initials: L
authors.lastname: García-García
authors.forename: M Álvaro
authors.initials: MÁ
authors.lastname: Berbis
authors.forename: Jessika
authors.initials: J
authors.lastname: Valero-Gónzalez
authors.forename: Sonsoles
authors.initials: S
authors.lastname: Martín-Santamaría
authors.forename: Ramon
authors.initials: R
authors.lastname: Hurtado-Guerrero
authors.forename: Juan L
authors.initials: JL
authors.lastname: Asensio
authors.forename: Jesús
authors.initials: J
authors.lastname: Jiménez-Barbero
authors.forename: Alberto
authors.initials: A
authors.lastname: Avenoza
authors.forename: Jesús H
authors.initials: JH
authors.lastname: Busto
authors.forename: Francisco
authors.initials: F
authors.lastname: Corzana
authors.forename: Jesús M
authors.initials: JM
authors.lastname: Peregrina
mesh_terms: D000595:Amino Acid Sequence; D015295:Antigens, Tumor-Associated, Carbohydrate / Q000737:chemistry / Q000276:immunology*; D006020:Glycopeptides / Q000737:chemistry / Q000276:immunology*; D006031:Glycosylation; D037102:Lectins / Q000276:immunology*; D008958:Models, Molecular; D056004:Molecular Dynamics Simulation; D008969:Molecular Sequence Data; D037121:Plant Lectins / Q000276:immunology*; D012694:Serine / Q000737:chemistry / Q000276:immunology; D030262:Soybean Proteins / Q000276:immunology*; D013912:Threonine / Q000737:chemistry / Q000276:immunology; D010835:Phytohemagglutinins
chemical_list: D015295:Antigens, Tumor-Associated, Carbohydrate; D006020:Glycopeptides; D037102:Lectins; D037121:Plant Lectins; D012694:Serine; D030262:Soybean Proteins; D013912:Threonine; C038095:Helix lectin; C040286:Tn antigen; C042242:Vicia lectins; C028824:soybean lectin; D010835:Phytohemagglutinins
keywords: conformation analysis; glycopeptides; molecular dynamics; molecular recognition; mucin