First synthesis of two deoxy Lewis(x) pentaosyl glycosphingolipids.
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.
Luo
Yun
Y
ZJU-ENS joint laboratory of Medicinal Chemistry, College of Pharmaceutical Sciences, Zhejiang University, Hangzhou, 310058, China.
Gourmala
Chafika
C
Dong
Dengxiang
D
Barbault
Florent
F
Fan
Botao
B
Hu
Yongzhou
Y
Zhang
Yongmin
Y
D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D006028:Glycosphingolipids / Q000138:chemical synthesis* / Q000737:chemistry; D016256:Lewis X Antigen / Q000031:analogs & derivatives; D008969:Molecular Sequence Data
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