Hideharu Ishida

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Organization: Gifu University
Department: 1 Department of Applied Bioorganic Chemistry
Title:
Co-reporter:Dr. Kohki Fujikawa;Shinya Nakashima;Miku Konishi;Tomoaki Fuse;Naoko Komura;Dr. Takayuki Ando;Dr. Hiromune Ando;Dr. Nobuhiro Yuki;Dr. Hideharu Ishida;Dr. Makoto Kiso
Chemistry - A European Journal 2011 Volume 17( Issue 20) pp:5641-5651
Publication Date(Web):
DOI:10.1002/chem.201003357

Abstract

The first synthesis of ganglioside GalNAc-GD1a, featuring efficient glycan assembly and a cyclic glucosyl ceramide as a versatile unit for ganglioside synthesis is described. Although ganglioside GalNAc-GD1a was first found as a brain ganglioside, IgG autoantibodies to GalNAc-GD1a were subsequently found to be closely related to a human peripheral-nerve disorder, Guillain–Barré syndrome, which is the commonest cause of acute flaccid paralysis worldwide. In this study, the characteristic hexasaccharide part carrying two sialic acid residues was synthesized efficiently by use of a readily accessible GM2-core unit as a common unit. The potentially difficult coupling of the oligosaccharide and ceramide moieties was carried out by using a cyclic glucosyl ceramide as a coupling partner for the hexasaccharide part, thereby successfully providing the framework of the target compound. Global deprotection delivered the homogenous ganglioside GalNAc-GD1a. An enzyme-linked immunosorbent assay showed that sera from patients with Guillain–Barré syndrome reacted both with natural and with synthetic GalNAc-GD1a.

Co-reporter:Kohki Fujikawa, Tomohiro Nohara, Akihiro Imamura, Hiromune Ando, Hideharu Ishida, Makoto Kiso
Tetrahedron Letters 2010 Volume 51(Issue 7) pp:1126-1130
Publication Date(Web):17 February 2010
DOI:10.1016/j.tetlet.2009.12.121
Co-reporter:Kohki Fujikawa, Akihiro Imamura, Hideharu Ishida, Makoto Kiso
Carbohydrate Research 2008 Volume 343(Issue 16) pp:2729-2734
Publication Date(Web):3 November 2008
DOI:10.1016/j.carres.2008.05.007
A novel analogue of ganglioside GM3, in which sphingosine was replaced with a phytosphingosine moiety, was synthesized by intramolecular glycosylation as a key step. Glucose, a reducing terminal of the saccharide, and phytoceramide were first tethered by succinic acid and the derivative used for the subsequent glycosidic bond formation. The obtained glycosyl phytoceramide was further glycosylated with the sialyl galactose residue to afford a fully protected GM3 derivative, which was converted into the desired, final compound by using conventional deprotection procedures.Novel strategy for the synthesis of gangliosides was developed by employing intramolecular glycosylation.
Co-reporter:Takeru Yoshikawa;Yuki Kato;Nobuhiro Yuki;Tomio Yabe
Glycoconjugate Journal 2008 Volume 25( Issue 6) pp:545-553
Publication Date(Web):2008 August
DOI:10.1007/s10719-008-9111-2
GM1 epitope tetrasaccharide was synthesized by a condensation of sialyl-α(2–3)-gal acceptor and gal-β(1–3)-GalN donor in a highly efficient manner. After introduction of mercaptohexanol to the tetrasaccharide, it was coupled to maleimide-activated KLH carrier protein to give the desired GM1 epitope-KLH conjugate.
2,2,2-TRIFLUORO-N-[2-(2-HYDROXYETHOXY)ETHYL]ACETAMIDE
b-D-Galactopyranoside, phenyl2-deoxy-1-thio-2-[[(2,2,2-trichloroethoxy)carbonyl]amino]-, 3,4,6-triacetate
Propanoic acid, 2,2-dimethyl-, 5-bromopentyl ester
Protein kinase Akt
Mitogen-activated protein kinase
α-D-Glucopyranoside, methyl 2,3,4-tris-O-(phenylmethyl)-6-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-
Phosphatidylinositol 3-kinase