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dc.contributor.authorFlorio, P
dc.contributor.authorThomson, RJ
dc.contributor.authorvon Itzstein, M
dc.date.accessioned2017-05-03T13:29:44Z
dc.date.available2017-05-03T13:29:44Z
dc.date.issued2000
dc.identifier.issn0008-6215
dc.identifier.doi10.1016/S0008-6215(00)00228-7
dc.identifier.urihttp://hdl.handle.net/10072/2980
dc.description.abstractIn 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.
dc.description.peerreviewedYes
dc.description.publicationstatusYes
dc.languageEnglish
dc.language.isoeng
dc.publisherPergamon
dc.publisher.placeUK
dc.relation.ispartofpagefrom445
dc.relation.ispartofpageto448
dc.relation.ispartofjournalCarbohydrate Research
dc.relation.ispartofvolume328
dc.subject.fieldofresearchMedicinal and biomolecular chemistry
dc.subject.fieldofresearchOrganic chemistry
dc.subject.fieldofresearchBiochemistry and cell biology
dc.subject.fieldofresearchHistory, heritage and archaeology
dc.subject.fieldofresearchcode3404
dc.subject.fieldofresearchcode3405
dc.subject.fieldofresearchcode3101
dc.subject.fieldofresearchcode43
dc.titleRapid access to uronic acid-based mimetics of Kdn2en from D-glucurono-6,3-lactone
dc.typeJournal article
dc.type.descriptionC1 - Articles
dc.type.codeC - Journal Articles
gro.facultyOffice of the Snr Dep Vice Chancellor, Institute for Glycomics
gro.date.issued2015-05-04T22:04:29Z
gro.hasfulltextNo Full Text
gro.griffith.authorvon Itzstein, Mark
gro.griffith.authorThomson, Robin J.


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