title: Chemical approach for the syntheses of GM4 isomers with sialic acid to non-natural linkage positions on galactose.
abstract: Cell-surface glycans containing sialic acid are involved in various biological phenomena. However, the syntheses of GM4 derivatives with (2 → 2) and (2 → 4) linkages have not been investigated to date. In this study, sialylation of all of the hydroxyl groups on galactose were investigated for the syntheses of GM4 isomers. Regioselective sialylation was achieved via protection of galactosyl acceptors using electron-rich benzyl groups. These synthetic sialylated glycans will prove to be useful tools for studying unidentified carbohydrate-mediated biological roles.
authors.affiliation: Graduate School of Engineering, Nagoya Institute of Technology, Gokiso-cho, Showa-ku, Nagoya 466-8555, Japan.
authors.forename: Kenta
authors.initials: K
authors.lastname: Kurimoto
authors.affiliation: Graduate School of Engineering, Nagoya Institute of Technology, Gokiso-cho, Showa-ku, Nagoya 466-8555, Japan.
authors.forename: Hatsuo
authors.initials: H
authors.lastname: Yamamura
authors.affiliation: Graduate School of Engineering, Nagoya Institute of Technology, Gokiso-cho, Showa-ku, Nagoya 466-8555, Japan. Electronic address: miyagawa.atsushi@nitech.ac.jp.
authors.forename: Atsushi
authors.initials: A
authors.lastname: Miyagawa
mesh_terms: D060326:Chemistry Techniques, Synthetic; D005690:Galactose / Q000737:chemistry*; D005732:Gangliosides / Q000138:chemical synthesis* / Q000737:chemistry*; D006031:Glycosylation; D006878:Hydroxides / Q000737:chemistry; D019158:N-Acetylneuraminic Acid / Q000737:chemistry*; D013237:Stereoisomerism; D013379:Substrate Specificity
chemical_list: D005732:Gangliosides; D006878:Hydroxides; C028253:ganglioside, GM4; C031356:hydroxide ion; D019158:N-Acetylneuraminic Acid; D005690:Galactose
keywords: Anomeric configuration; GM4; Oxazolidinone; Sialylation