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  • Rapid access to uronic acid-based mimetics of Kdn2en from D-glucurono-6,3-lactone

    Author(s)
    Florio, P
    Thomson, RJ
    von Itzstein, M
    Griffith University Author(s)
    von Itzstein, Mark
    Thomson, Robin J.
    Year published
    2000
    Metadata
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    Abstract
    In order to prepare 3-aminopropyl glycosides of Neu5Ac-a-(2?6')-lactosamine trisaccharide 1, and its N-glycolyl containing analogue Neu5Gc-a-(2?6')-lactosamine 2, a series of lactosamine acceptors with two, three, and four free OH groups in the galactose residue was studied in glycosylations with a conventional sialyl donor phenyl [methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio--glycero-a- and ߭-galacto-2-nonulopyranosid]onates (3) and a new donor phenyl [methyl 4,7,8,9-tetra-O-acetyl-5-(N-tert-butoxycarbonylacetamido)-3,5-dideoxy-2-thio--glycero-a- and ߭-galacto-2-nonulopyranosid]onates (4), respectively. The ...
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    In order to prepare 3-aminopropyl glycosides of Neu5Ac-a-(2?6')-lactosamine trisaccharide 1, and its N-glycolyl containing analogue Neu5Gc-a-(2?6')-lactosamine 2, a series of lactosamine acceptors with two, three, and four free OH groups in the galactose residue was studied in glycosylations with a conventional sialyl donor phenyl [methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio--glycero-a- and ߭-galacto-2-nonulopyranosid]onates (3) and a new donor phenyl [methyl 4,7,8,9-tetra-O-acetyl-5-(N-tert-butoxycarbonylacetamido)-3,5-dideoxy-2-thio--glycero-a- and ߭-galacto-2-nonulopyranosid]onates (4), respectively. The lactosamine 4',6'-diol acceptor was found to be the most efficient in glycosylation with both 3 and 4, while imide-type donor 4 gave slightly higher yields with all acceptors, and isolation of the reaction products was more convenient. In the trisaccharides, obtained by glycosylation with donor 4, the 5-(N-tert-butoxycarbonylacetamido) moiety in the neuraminic acid could be efficiently transformed into the desired N-glycolyl fragment, indicating that such protected oligosaccharide derivatives are valuable precursors of sialo-oligosaccharides containing N-modified analogues of Neu5Ac.
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    Journal Title
    Carbohydrate Research
    Volume
    328
    DOI
    https://doi.org/10.1016/S0008-6215(00)00228-7
    Subject
    Medicinal and biomolecular chemistry
    Organic chemistry
    Biochemistry and cell biology
    History, heritage and archaeology
    Publication URI
    http://hdl.handle.net/10072/2980
    Collection
    • Journal articles

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