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dc.contributor.authorWeïwer, M.
dc.contributor.authorChen, C.C.
dc.contributor.authorKemp, M.M.
dc.contributor.authorLinhardt, Robert J.
dc.date2009
dc.date.accessioned2022-06-23T04:01:51Z
dc.date.available2022-06-23T04:01:51Z
dc.date.issued2009-06-01
dc.identifier.citationSynthesis and biological evaluation of 1,2,3-triazole linked sialic acid derivatives as neuraminidase inhibitors, M. Weïwer, C.-C. Chen, M. M. Kemp, R. J. Linhardt, European Journal of Organic Chemistry, 2611–2620, 2009.
dc.identifier.issn10990690
dc.identifier.issn1434193X
dc.identifier.urihttps://hdl.handle.net/20.500.13015/5219
dc.identifier.urihttps://doi.org/10.1002/ejoc.200900117
dc.descriptionEuropean Journal of Organic Chemistry, 2611–2620
dc.descriptionNote : if this item contains full text it may be a preprint, author manuscript, or a Gold OA copy that permits redistribution with a license such as CC BY. The final version is available through the publisher’s platform.
dc.description.abstractα-Sialic acid azide 1 has been used as a substrate for the efficient preparation of 1,2,3-triazole derivatives of sialic acid using the copper-catalyzed azide-alkyne Huisgen cycloaddition ("click chemistry"). Our approach is to generate non-natural N-glycosides of sialic acid that are resistant to neuraminidase catalyzed hydrolysis as opposed to the natural O-glycosides. These N-glycosides would act as neuraminidase inhibitors to prevent the release of new virions. As a preliminary study, a small library of 1,2,3-triazole-linked sialic acid derivatives has been synthesized in 71-89% yield. A disaccharide mimic of sialic acid has also been prepared using the α-sialic acid azide 1 and a C-8 propargyl sialic acid acceptor in 68% yield. A model sialic acid coated dendrimer was also synthesized from a per-propargylated pentaerythritol acceptor. These novel sialic acid derivatives were then evaluated as potential neuraminidase inhibitors using a 96-well plate fluorescence assay; micromolar IC50 values were observed, comparable to the known sialidase inhibitor Neu5Ac2en.
dc.languageen_US
dc.language.isoENG
dc.publisherEuropean Chemical Societies Publishing
dc.relation.ispartofThe Linhardt Research Labs Online Collection
dc.relation.ispartofRensselaer Polytechnic Institute, Troy, NY
dc.relation.ispartofEuropean Journal of Organic Chemistry
dc.relation.urihttps://harc.rpi.edu/
dc.subjectBiology
dc.subjectChemistry and chemical biology
dc.subjectChemical and biological engineering
dc.subjectBiomedical engineering
dc.titleSynthesis and biological evaluation of 1,2,3-triazole linked sialic acid derivatives as neuraminidase inhibitors
dc.typeArticle
dcterms.accessRightsA full text version is available in DSpace@RPI
dcterms.isPartOfJournal
dcterms.isVersionOfhttps://doi.org/10.1002/ejoc.200900117
dc.rights.holderIn Copyright : this Item is protected by copyright and/or related rights. You are free to use this Item in any way that is permitted by the copyright and related rights legislation that applies to your use. For other uses you need to obtain permission from the rights-holder(s). https://rightsstatements.org/page/InC/1.0/
dc.creator.identifierhttps://orcid.org/0000-0003-2219-5833
dc.relation.departmentThe Linhardt Research Labs.
dc.relation.departmentThe Shirley Ann Jackson, Ph.D. Center for Biotechnology and Interdisciplinary Studies (CBIS)
rpi.description.pages2611-2620


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