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https://doi.org/10.1002/chem.201003357
Title: | The first total synthesis of ganglioside GalNAc-GD1a, a target molecule for autoantibodies in guillain-barré syndrome | Authors: | Fujikawa, K. Nakashima, S. Konishi, M. Fuse, T. Komura, N. Ando, H. Ando, T. Yuki, N. Ishida, H. Kiso, M. |
Keywords: | gangliosides Guillain-Barré syndrome natural products sialic acids total synthesis |
Issue Date: | 9-May-2011 | Citation: | Fujikawa, K., Nakashima, S., Konishi, M., Fuse, T., Komura, N., Ando, H., Ando, T., Yuki, N., Ishida, H., Kiso, M. (2011-05-09). The first total synthesis of ganglioside GalNAc-GD1a, a target molecule for autoantibodies in guillain-barré syndrome. Chemistry - A European Journal 17 (20) : 5641-5651. ScholarBank@NUS Repository. https://doi.org/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. © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. | Source Title: | Chemistry - A European Journal | URI: | http://scholarbank.nus.edu.sg/handle/10635/125517 | ISSN: | 09476539 | DOI: | 10.1002/chem.201003357 |
Appears in Collections: | Staff Publications |
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