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A First Total Synthesis of a Hybrid-Type Ganglioside Associated with Amyotrophic Lateral Sclerosis-Like Disorder†
Article first published online: 5 NOV 2010
Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Chemistry - A European Journal
Volume 17, Issue 2, pages 588–597, January 10, 2011
How to Cite
Nakashima, S., Ando, H., Imamura, A., Yuki, N., Ishida, H. and Kiso, M. (2011), A First Total Synthesis of a Hybrid-Type Ganglioside Associated with Amyotrophic Lateral Sclerosis-Like Disorder. Chem. Eur. J., 17: 588–597. doi: 10.1002/chem.201002184
- Issue published online: 5 JAN 2011
- Article first published online: 5 NOV 2010
- Manuscript Received: 30 JUL 2010
- grant-in-aid for Scientific Research. Grant Numbers: 1701007, 22380067
- natural products;
- total synthesis
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.