title: First synthesis of two deoxy Lewis(x) pentaosyl glycosphingolipids.
abstract: The Lewis(x)-Lewis(x) interaction has been increasingly studied, using a variety of techniques including nuclear magnetic resonance spectroscopy, mass spectrometry, vesicle adhesion, atomic force microscopy, and surface plasmon resonance spectroscopy. However, the detailed molecular mechanism of these weak, divalent cation dependent interactions remains unclear, and new models are needed to probe the nature of this phenomenon in term of key roles of the different hydroxyl groups on Lewis(x) trisaccharide determinant involved in the Lewis(x)-Lewis(x) interaction. An interesting solution is to synthesize a series of Lewis(x) pentaosyl glycosphingolipid derivatives in which one of the eight hydroxyl groups of Lewis(x) trisaccharide is replaced by a hydrogen atom, and to test the adhesion induced by interaction of these derivatives, in order to gain insight into the functions played by the hydroxyl groups of the Lewis(x) trisaccharide. This article describes the synthesis of 3d-deoxy and 4d-deoxy Lewis(x) pentaosyl glycosphingolipids, to be used for study of the Lewis(x)-Lewis(x) interaction.
authors.affiliation: ZJU-ENS joint laboratory of Medicinal Chemistry, College of Pharmaceutical Sciences, Zhejiang University, Hangzhou, 310058, China.
authors.forename: Yun
authors.initials: Y
authors.lastname: Luo
authors.forename: Chafika
authors.initials: C
authors.lastname: Gourmala
authors.forename: Dengxiang
authors.initials: D
authors.lastname: Dong
authors.forename: Florent
authors.initials: F
authors.lastname: Barbault
authors.forename: Botao
authors.initials: B
authors.lastname: Fan
authors.forename: Yongzhou
authors.initials: Y
authors.lastname: Hu
authors.forename: Yongmin
authors.initials: Y
authors.lastname: Zhang
mesh_terms: D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D006028:Glycosphingolipids / Q000138:chemical synthesis* / Q000737:chemistry; D016256:Lewis X Antigen / Q000031:analogs & derivatives; D008969:Molecular Sequence Data
chemical_list: C539841:(3-deoxyxylohexopyranosyl)-1-4-(1-fucopyranosyl-1-3)-(2-deoxy-2-acetamidoglucopyranosyl)-1-3-galactopyranosyl-1-4-glucopyranosyl-(1-1)-2-octadecanamido-4-octadecene-1,3-diol; C539842:(4-deoxyxylohexopyranosyl)-1-4-(1-fucopyranosyl-1-3)-(2-deoxy-2-acetamidoglucopyranosyl)-1-3-galactopyranosyl-1-4-glucopyranosyl-(1-1)-2-octadecanamido-4-octadecene-1,3-diol; D006028:Glycosphingolipids; D016256:Lewis X Antigen