Chemical approach for the syntheses of GM4 isomers with sialic acid to non-natural linkage positions on galactose

Kenta Kurimoto; Hatsuo Yamamura; Atsushi Miyagawa

doi:10.1016/j.carres.2014.10.018

Chemical approach for the syntheses of GM4 isomers with sialic acid to non-natural linkage positions on galactose

Carbohydr Res. 2015 Jan 12:401:39-50. doi: 10.1016/j.carres.2014.10.018. Epub 2014 Oct 29.

Authors

Kenta Kurimoto¹, Hatsuo Yamamura¹, Atsushi Miyagawa²

Affiliations

¹ Graduate School of Engineering, Nagoya Institute of Technology, Gokiso-cho, Showa-ku, Nagoya 466-8555, Japan.
² Graduate School of Engineering, Nagoya Institute of Technology, Gokiso-cho, Showa-ku, Nagoya 466-8555, Japan. Electronic address: miyagawa.atsushi@nitech.ac.jp.

PMID: 25464080
DOI: 10.1016/j.carres.2014.10.018

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.

Keywords: Anomeric configuration; GM4; Oxazolidinone; Sialylation.

MeSH terms

Chemistry Techniques, Synthetic
Galactose / chemistry*
Gangliosides / chemical synthesis*
Gangliosides / chemistry*
Glycosylation
Hydroxides / chemistry
N-Acetylneuraminic Acid / chemistry*
Stereoisomerism
Substrate Specificity

Substances

Gangliosides
Hydroxides
ganglioside, GM4
hydroxide ion
N-Acetylneuraminic Acid
Galactose