dc.contributor.author | Florio, P | |
dc.contributor.author | Thomson, RJ | |
dc.contributor.author | von Itzstein, M | |
dc.date.accessioned | 2017-05-03T13:29:44Z | |
dc.date.available | 2017-05-03T13:29:44Z | |
dc.date.issued | 2000 | |
dc.identifier.issn | 0008-6215 | |
dc.identifier.doi | 10.1016/S0008-6215(00)00228-7 | |
dc.identifier.uri | http://hdl.handle.net/10072/2980 | |
dc.description.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 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.peerreviewed | Yes | |
dc.description.publicationstatus | Yes | |
dc.language | English | |
dc.language.iso | eng | |
dc.publisher | Pergamon | |
dc.publisher.place | UK | |
dc.relation.ispartofpagefrom | 445 | |
dc.relation.ispartofpageto | 448 | |
dc.relation.ispartofjournal | Carbohydrate Research | |
dc.relation.ispartofvolume | 328 | |
dc.subject.fieldofresearch | Medicinal and biomolecular chemistry | |
dc.subject.fieldofresearch | Organic chemistry | |
dc.subject.fieldofresearch | Biochemistry and cell biology | |
dc.subject.fieldofresearch | History, heritage and archaeology | |
dc.subject.fieldofresearchcode | 3404 | |
dc.subject.fieldofresearchcode | 3405 | |
dc.subject.fieldofresearchcode | 3101 | |
dc.subject.fieldofresearchcode | 43 | |
dc.title | Rapid access to uronic acid-based mimetics of Kdn2en from D-glucurono-6,3-lactone | |
dc.type | Journal article | |
dc.type.description | C1 - Articles | |
dc.type.code | C - Journal Articles | |
gro.faculty | Office of the Snr Dep Vice Chancellor, Institute for Glycomics | |
gro.date.issued | 2015-05-04T22:04:29Z | |
gro.hasfulltext | No Full Text | |
gro.griffith.author | von Itzstein, Mark | |
gro.griffith.author | Thomson, Robin J. | |