Studies on the alpha-(1-->4)- and alpha-(1-->8)-fucosylation of sialic acid for the total assembly of the glycan portions of complex HPG-series gangliosides

Hiromune Ando; Hiroyo Shimizu; Yukari Katano; Yusuke Koike; Sachiko Koizumi; Hideharu Ishida; Makoto Kiso

doi:10.1016/j.carres.2006.03.017

Studies on the alpha-(1-->4)- and alpha-(1-->8)-fucosylation of sialic acid for the total assembly of the glycan portions of complex HPG-series gangliosides

Carbohydr Res. 2006 Jul 24;341(10):1522-32. doi: 10.1016/j.carres.2006.03.017. Epub 2006 Apr 5.

Authors

Hiromune Ando¹, Hiroyo Shimizu, Yukari Katano, Yusuke Koike, Sachiko Koizumi, Hideharu Ishida, Makoto Kiso

Affiliation

¹ Division of Instrumental Analysis, Life Science Research Center, Gifu University, 1-1 Yanagido, Gifu-shi, Gifu 501-1193, Japan. hando@cc.gifu-u.ac.jp

PMID: 16603136
DOI: 10.1016/j.carres.2006.03.017

Abstract

A synthetic study on alpha-(1-->4) and alpha-(1-->8)-fucosylation of sialic acid is reported, with the ultimate aim being the total assembly of the glycan portion of HPG-series gangliosides. In both types of fucosylations, the combination of a phenylthio fucosyl donor and a 1,5-lactamized acceptor provided high-yielding glycosylations to afford alpha-fucosyl-sialic acid sequences. The obtained alpha-Fucp-(1-->8)-NeupNAc glycan having a 1,5-lactam bridge has been successfully transformed into the corresponding glycosyl donor.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Carbohydrate Sequence
Fucose / chemistry*
Gangliosides / chemical synthesis*
Glycosylation
Molecular Sequence Data
N-Acetylneuraminic Acid / chemistry*

Substances

Gangliosides
HPG-7 ganglioside
Fucose
N-Acetylneuraminic Acid