title: A synthetic heparan sulfate pentasaccharide, exclusively containing L-iduronic acid, displays higher affinity for FGF-2 than its D-glucuronic acid-containing isomers.
abstract: It has been suggested that the FGF-2 binding site on heparan sulfate chains is a trisulfated pentasaccharide containing three hexuronic acid units. The configuration at C-5 of two of them being undetermined, we have synthesized the four possible pentasaccharides, and have evaluated their FGF-2 binding affinity through in vitro biological assays. The pentasaccharide containing L-iduronic acid as the sole hexuronic acid showed higher affinity for FGF-2 than the other pentasaccharides, where one hexuronic acid unit at least is D-glucuronic acid.
authors.affiliation: Ecole Normale Supérieure, Département de Chimie, Associé au CNRS, Paris, France.
authors.forename: J
authors.initials: J
authors.lastname: Kovensky
authors.forename: P
authors.initials: P
authors.lastname: Duchaussoy
authors.forename: F
authors.initials: F
authors.lastname: Bono
authors.forename: M
authors.initials: M
authors.lastname: Salmivirta
authors.forename: P
authors.initials: P
authors.lastname: Sizun
authors.forename: J M
authors.initials: JM
authors.lastname: Herbert
authors.forename: M
authors.initials: M
authors.lastname: Petitou
authors.forename: P
authors.initials: P
authors.lastname: Sinaÿ
mesh_terms: D001011:Aorta / Q000166:cytology / Q000187:drug effects / Q000378:metabolism; D001665:Binding Sites; D002240:Carbohydrate Sequence; D002455:Cell Division / Q000187:drug effects; D002478:Cells, Cultured; D016222:Fibroblast Growth Factor 2 / Q000378:metabolism* / Q000494:pharmacology; D020723:Glucuronic Acid / Q000737:chemistry*; D006497:Heparan Sulfate / Q000138:chemical synthesis / Q000737:chemistry / Q000378:metabolism*; D006801:Humans; D007067:Iduronic Acid / Q000737:chemistry*; D007536:Isomerism; D008969:Molecular Sequence Data; D009131:Muscle, Smooth, Vascular / Q000166:cytology / Q000187:drug effects / Q000378:metabolism; D009844:Oligosaccharides / Q000138:chemical synthesis / Q000737:chemistry
chemical_list: D016222:Fibroblast Growth Factor 2; D020723:Glucuronic Acid; D006497:Heparan Sulfate; D007067:Iduronic Acid; D009844:Oligosaccharides