title: Potent fluoro-oligosaccharide probes of adhesion in Toxoplasmosis.
abstract: Unnatural, NMR- and MRI-active fluorinated sugar probes, designed and synthesised to bind to the pathogenic protein TgMIC1 from Toxoplasma gondii, were found to display binding potency equal to and above that of the natural ligand. Dissection of the binding mechanism and modes, including the first X-ray crystal structures of a fluoro-oligosaccharide bound to a lectin, demonstrate that it is possible to create effective fluorinated probe ligands for the study of, and perhaps intervention in, sugar-protein binding events.
authors.affiliation: Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford OX13TA, UK.
authors.forename: Sarah A
authors.initials: SA
authors.lastname: Allman
authors.forename: Henrik H
authors.initials: HH
authors.lastname: Jensen
authors.forename: Balakumar
authors.initials: B
authors.lastname: Vijayakrishnan
authors.forename: James A
authors.initials: JA
authors.lastname: Garnett
authors.forename: Ester
authors.initials: E
authors.lastname: Leon
authors.forename: Yan
authors.initials: Y
authors.lastname: Liu
authors.forename: Daniel C
authors.initials: DC
authors.lastname: Anthony
authors.forename: Nicola R
authors.initials: NR
authors.lastname: Sibson
authors.forename: Ten
authors.initials: T
authors.lastname: Feizi
authors.forename: Stephen
authors.initials: S
authors.lastname: Matthews
authors.forename: Benjamin G
authors.initials: BG
authors.lastname: Davis
mesh_terms: D050260:Carbohydrate Metabolism; D002448:Cell Adhesion; D015815:Cell Adhesion Molecules / Q000737:chemistry / Q000378:metabolism; D018360:Crystallography, X-Ray; D004187:Disaccharides / Q000138:chemical synthesis / Q000737:chemistry; D054879:Halogenation; D015335:Molecular Probes / Q000138:chemical synthesis / Q000737:chemistry* / Q000378:metabolism*; D009844:Oligosaccharides / Q000138:chemical synthesis / Q000737:chemistry* / Q000378:metabolism*; D015800:Protozoan Proteins / Q000737:chemistry / Q000378:metabolism; D011956:Receptors, Cell Surface / Q000378:metabolism; D014122:Toxoplasma / Q000166:cytology* / Q000378:metabolism; D014123:Toxoplasmosis / Q000469:parasitology*
chemical_list: D015815:Cell Adhesion Molecules; D004187:Disaccharides; C105877:MIC1 protein, Toxoplasma gondii; D015335:Molecular Probes; D009844:Oligosaccharides; D015800:Protozoan Proteins; D011956:Receptors, Cell Surface; C055213:saccharide-binding proteins