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A First Total Synthesis of a Hybrid‐Type Ganglioside Associated with Amyotrophic Lateral Sclerosis‐Like Disorder
Author(s) -
Nakashima Shinya,
Ando Hiromune,
Imamura Akihiro,
Yuki Nobuhiro,
Ishida Hideharu,
Kiso Makoto
Publication year - 2011
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201002184
Subject(s) - amyotrophic lateral sclerosis , ganglioside , medicine , neuroscience , psychology , biology , disease , genetics
Abstract The hybrid ganglioside X1, which was identified in the bovine brain, was synthesized for the first time. Ganglioside X1 is believed to be involved in the development of amyotrophic lateral sclerosis‐like disorders in patients with neurological disorders after treatment with bovine brain gangliosides. A convergent approach using two branched glycan units, the GM2‐core trisaccharide and the lacto‐ganglio tetrasaccharide, efficiently provided the highly branched heptasaccharide part of ganglioside X1, which was conjugated with the ceramide part to produce the protected ganglioside X1. Global deprotection delivered homogenous ganglioside X1, with which serum from the patient was reacted.