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

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Title Rapid access to uronic acid-based mimetics of Kdn2en from D-glucurono-6,3-lactone
Author von Itzstein, Mark; Florio, Pas.; Thomson, Robin; Thomson,Robin J.
Journal Name Carbohydrate Research
Year Published 2000
Place of publication UK
Publisher Pergamon
Abstract In order to prepare 3-aminopropyl glycosides of Neu5Ac-α-(2→6′)-lactosamine trisaccharide 1, and its N-glycolyl containing analogue Neu5Gc-α-(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-α- and β--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-α- and β--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.
Peer Reviewed Yes
Published Yes
Alternative URI http://dx.doi.org/10.1016/S0008-6215(00)00228-7
Volume 328
Page from 445
Page to 448
ISSN 0008-6215
Date Accessioned 2001-01-01
Date Available 2015-05-04T22:04:29Z
Language en_US
Research Centre Institute for Glycomics
Subject PRE2009-Science & Technology
URI http://hdl.handle.net/10072/2980
Publication Type Article in Scholarly Refereed Journal
Publication Type Code c1

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