title: Total syntheses of disulphated glycosphingolipid SB1a and the related monosulphated SM1a.
abstract: Total syntheses of two natural sulphoglycolipids, disulphated glycosphingolipid SB1a and the structurally related monosulphated SM1a, are described. They have common glycan sequences and ceramide moieties and are associated with human epithelial carcinomas. The syntheses featured efficient glycan assembly and the glucosyl ceramide cassette as a versatile building block. The binding of the synthetic sulphoglycolipids by the carcinoma-specific monoclonal antibody AE3 was investigated using carbohydrate microarray technology.
authors.affiliation: Department of Applied Bioorganic Chemistry, Faculty of Applied Biological Sciences, Gifu University, 1-1 Yanagido, Gifu-shi, Gifu 501-1193, Japan. aimamura@gifu-u.ac.jp kiso@gifu-u.ac.jp.
authors.forename: Haruka
authors.initials: H
authors.lastname: Hirose
authors.forename: Hideki
authors.initials: H
authors.lastname: Tamai
authors.forename: Chao
authors.initials: C
authors.lastname: Gao
authors.forename: Akihiro
authors.initials: A
authors.lastname: Imamura
authors.forename: Hiromune
authors.initials: H
authors.lastname: Ando
authors.forename: Hideharu
authors.initials: H
authors.lastname: Ishida
authors.forename: Ten
authors.initials: T
authors.lastname: Feizi
authors.forename: Makoto
authors.initials: M
authors.lastname: Kiso
mesh_terms: D002277:Carcinoma / Q000737:chemistry; D002518:Ceramides / Q000138:chemical synthesis / Q000737:chemistry; D006028:Glycosphingolipids / Q000138:chemical synthesis* / Q000737:chemistry; D006801:Humans; D046228:Microarray Analysis; D011134:Polysaccharides / Q000138:chemical synthesis / Q000737:chemistry; D013457:Sulfur Compounds / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D002518:Ceramides; D006028:Glycosphingolipids; D011134:Polysaccharides; D013457:Sulfur Compounds