title: The influence of the aromatic aglycon of galactoclusters on the binding of LecA: a case study with O-phenyl, S-phenyl, O-benzyl, S-benzyl, O-biphenyl and O-naphthyl aglycons.
abstract: A library of 24 new mannose-centered tetragalactoclusters with four different linkers (di- and triethyleneglycol with phosphodiester or phosphorothioate linkages) and six different aromatic aglycons (O-phenyl, S-phenyl, O-benzyl, S-benzyl, O-biphenyl and O-naphthyl) was synthesized. Their interactions with LecA were evaluated on a DNA Directed Immobilization (DDI) based glycocluster array allowing the determination of their IC50 against lactose and the evaluation of their dissociation constant (Kd). Finally, the docking simulations confirm the experimental results and demonstrated that the better affinity of O-biphenyl- and O-naphthyl-galactoside is due to a double interaction between the aromatic ring and the histidine 50 and proline 51 of LecA.
authors.affiliation: Institut des Biomolécules Max Mousseron (IBMM), UMR 5247 CNRS-UM1-UM2, ENSCM, Université Montpellier 2, place E. Bataillon, CC1704, 34095 Montpellier cedex 5, France. morvan@univ-montp2.fr.
authors.forename: Francesca
authors.initials: F
authors.lastname: Casoni
authors.forename: Lucie
authors.initials: L
authors.lastname: Dupin
authors.forename: Gérard
authors.initials: G
authors.lastname: Vergoten
authors.forename: Albert
authors.initials: A
authors.lastname: Meyer
authors.forename: Caroline
authors.initials: C
authors.lastname: Ligeour
authors.forename: Thomas
authors.initials: T
authors.lastname: Géhin
authors.forename: Olivier
authors.initials: O
authors.lastname: Vidal
authors.forename: Eliane
authors.initials: E
authors.lastname: Souteyrand
authors.forename: Jean-Jacques
authors.initials: JJ
authors.lastname: Vasseur
authors.forename: Yann
authors.initials: Y
authors.lastname: Chevolot
authors.forename: François
authors.initials: F
authors.lastname: Morvan
mesh_terms: D018829:Adhesins, Bacterial / Q000378:metabolism*; D001386:Azides / Q000737:chemistry*; D001713:Biphenyl Compounds / Q000737:chemistry*; D005690:Galactose / Q000737:chemistry*; D005697:Galactosides / Q000138:chemical synthesis / Q000737:chemistry*; D008958:Models, Molecular; D009284:Naphthols / Q000737:chemistry*
chemical_list: D018829:Adhesins, Bacterial; D001386:Azides; D001713:Biphenyl Compounds; D005690:Galactose; D005697:Galactosides; D009284:Naphthols; C102929:LecA protein, bacteria; C005366:naphthyl acetate; C010574:biphenyl