title: The conformation of the C-glycosyl analogue of N-acetyl-lactosamine in the free state and bound to a toxic plant agglutinin and human adhesion/growth-regulatory galectin-1.
abstract: The conformational behavior of the C-glycoside analogue of N-acetyl-lactosamine, beta-C-Gal-(1-->4)-beta-GlcNAc-OMe, 1, has been studied using a combination of molecular mechanics calculations and NMR spectroscopy (J and NOE data). It is shown that the C-disaccharide populates three distinctive conformational families in solution, the major one being the anti-psi conformation. Of note, this conformation is only marginally populated for the O-disaccharide. Due to its conspicuous role in the regulation of adhesion, growth and tissue invasion of tumors and its avid binding to N-acetyl-lactosamine human, galectin-1 was tested as a receptor. This endogenous lectin recognizes a local minimum of 1, the syn-PhiPsi conformer, and thus a conformational selection process is correlated with the molecular recognition event.
authors.affiliation: Ecole Normale Supérieure, Département de Chimie, UMR CNRS 8642, 24, rue Lhomond, 75231 Paris Cedex 05, France.
authors.forename: Víctor
authors.initials: V
authors.lastname: García-Aparicio
authors.forename: Matthieu
authors.initials: M
authors.lastname: Sollogoub
authors.forename: Yves
authors.initials: Y
authors.lastname: Blériot
authors.forename: Virginie
authors.initials: V
authors.lastname: Colliou
authors.forename: Sabine
authors.initials: S
authors.lastname: André
authors.forename: Juan L
authors.initials: JL
authors.lastname: Asensio
authors.forename: F Javier
authors.initials: FJ
authors.lastname: Cañada
authors.forename: Hans-Joachim
authors.initials: HJ
authors.lastname: Gabius
authors.forename: Pierre
authors.initials: P
authors.lastname: Sinaÿ
authors.forename: Jesús
authors.initials: J
authors.lastname: Jiménez-Barbero
mesh_terms: D000117:Acetylglucosamine / Q000737:chemistry; D000606:Amino Sugars / Q000737:chemistry*; D002236:Carbohydrate Conformation; D002448:Cell Adhesion; D002455:Cell Division; D004187:Disaccharides / Q000737:chemistry; D037483:Galectin 1 / Q000737:chemistry*; D006027:Glycosides / Q000737:chemistry*; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D037121:Plant Lectins / Q000737:chemistry / Q000633:toxicity*
chemical_list: D000606:Amino Sugars; D004187:Disaccharides; D037483:Galectin 1; D006027:Glycosides; D037121:Plant Lectins; C032233:lactosamine; D000117:Acetylglucosamine