title: Total synthesis of a sialyl Lewis(x) derivative for the diagnosis of cancer.
abstract: The total synthesis of aminoethyl glycoside of sialyl Lewis(x) (sLe(x)) is described. A galactose donor was condensed with a diol of glucosamine to afford regioselectively a β1,4 linked disaccharide, which was further stereoselectively fucosylated to provide a protected Lewis(x) trisaccharide. After chemical modification, the trisaccharide was sialylated to give regio- and stereoselectively an azidoethyl glycoside of sLe(x). Finally, deprotection and azide reduction afforded the target compound. This compound will be coupled with protein and then be used to conduct further preclinical studies for the diagnosis of cancer.
authors: Institut Parisien de Chimie Moléculaire, CNRS UMR 7201, Université Pierre et Marie Curie-Paris 6, 4 Place Jussieu, 75005 Paris, France; ZJU-ENS Joint Laboratory of Medicinal Chemistry, College of Pharmaceutical Sciences, Zhejiang University, Hangzhou 310058, China.
authors: Dan
authors: D
authors: Lu
authors: ZJU-ENS Joint Laboratory of Medicinal Chemistry, College of Pharmaceutical Sciences, Zhejiang University, Hangzhou 310058, China.
authors: Yongzhou
authors: Y
authors: Hu
authors: Institute for Interdisciplinary Research, Jianghan University, Wuhan Economic and Technological Development Zone, Wuhan 430056, China.
authors: Xianran
authors: X
authors: He
authors: Institut Parisien de Chimie Moléculaire, CNRS UMR 7201, Université Pierre et Marie Curie-Paris 6, 4 Place Jussieu, 75005 Paris, France.
authors: Matthieu
authors: M
authors: Sollogoub
authors: Institut Parisien de Chimie Moléculaire, CNRS UMR 7201, Université Pierre et Marie Curie-Paris 6, 4 Place Jussieu, 75005 Paris, France; ZJU-ENS Joint Laboratory of Medicinal Chemistry, College of Pharmaceutical Sciences, Zhejiang University, Hangzhou 310058, China; Institute for Interdisciplinary Research, Jianghan University, Wuhan Economic and Technological Development Zone, Wuhan 430056, China. Electronic address: yongmin.zhang@upmc.fr.
authors: Yongmin
authors: Y
authors: Zhang
mesh_terms: D019040:E-Selectin / Q000737:chemistry* / Q000302:isolation & purification; D005944:Glucosamine / Q000737:chemistry; D006801:Humans; D008024:Ligands; D009369:Neoplasms / Q000175:diagnosis* / Q000473:pathology; D009844:Oligosaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D000080506:Sialyl Lewis X Antigen; D014312:Trisaccharides / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D019040:E-Selectin; D008024:Ligands; D009844:Oligosaccharides; D000080506:Sialyl Lewis X Antigen; D014312:Trisaccharides; D005944:Glucosamine
keywords: Cancer; E-selectin; Glycosylation; Regio- and stereoselectivity; Sialyl Lewis(x); Total synthesis