| The First Total Synthesis of Ganglioside GalNAc-GD1a, a Target Molecule for Autoantibodies in Guillain-Barré Syndrome. | |
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MedLine Citation:
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PMID: 21469228 Owner: NLM Status: Publisher |
Abstract/OtherAbstract:
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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. |
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Authors:
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Kohki Fujikawa; Shinya Nakashima; Miku Konishi; Tomoaki Fuse; Naoko Komura; Takayuki Ando; Hiromune Ando; Nobuhiro Yuki; Hideharu Ishida; Makoto Kiso |
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Publication Detail:
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Type: JOURNAL ARTICLE Date: 2011-4-5 |
Journal Detail:
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Title: Chemistry (Weinheim an der Bergstrasse, Germany) Volume: - ISSN: 1521-3765 ISO Abbreviation: - Publication Date: 2011 Apr |
Date Detail:
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Created Date: 2011-4-6 Completed Date: - Revised Date: - |
Medline Journal Info:
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Nlm Unique ID: 9513783 Medline TA: Chemistry Country: - |
Other Details:
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Languages: ENG Pagination: - Citation Subset: - |
Copyright Information:
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Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. |
Affiliation:
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Department of Applied Bioorganic Chemistry, Gifu University, 1-1 Yanagido, Gifu-shi, Gifu 501-1193 (Japan), Fax: (+81) 58-293-3452, (+81) 58-293-2918 hando@ gifu-u.ac.jp,; Department of Applied Bioorganic Chemistry, Institute for Integrated Cell-Material Sciences (WPI program), Kyoto University, Yoshida Ushinomiya-cho, Sakyo-ku, Kyoto 606-8501 (Japan). |
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From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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