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dc.contributor.authorThanh, Giangen_US
dc.contributor.authorAbbenante, Giovannien_US
dc.contributor.authorAdamson, Georgeen_US
dc.contributor.authorBecker, Bernden_US
dc.contributor.authorClark, Chrisen_US
dc.contributor.authorCondie, Glennen_US
dc.contributor.authorFalzun, Taniaen_US
dc.contributor.authorGrathwohl, Matthiasen_US
dc.contributor.authorGupta, Praveeren_US
dc.contributor.authorHanson, Michaelen_US
dc.contributor.authorHuynh, Ngocen_US
dc.contributor.authorKatavic, Peteren_US
dc.contributor.authorKuipers, Krystleen_US
dc.contributor.authorLam, Annen_US
dc.contributor.authorLiu, Ligongen_US
dc.contributor.authorMann, Marettaen_US
dc.contributor.authorMason, Jeffen_US
dc.contributor.authorMcKeveney, Declanen_US
dc.contributor.authorMuldoon, Craigen_US
dc.contributor.authorPearson, Andrewen_US
dc.contributor.authorRajaratnam, Premrajen_US
dc.contributor.authorRyan, Sarahen_US
dc.contributor.authorTometzki, Gerryen_US
dc.contributor.authorVerquin, Geraldineen_US
dc.contributor.authorWaanders, Jenniferen_US
dc.contributor.authorWest, Michaelen_US
dc.contributor.authorWilcox, Neilen_US
dc.contributor.authorWimmer, Norberten_US
dc.contributor.authorYau, Annikaen_US
dc.contributor.authorZuegg, Johannesen_US
dc.contributor.authorMeutermans, Wimen_US
dc.date.accessioned2017-05-03T13:03:36Z
dc.date.available2017-05-03T13:03:36Z
dc.date.issued2010en_US
dc.date.modified2010-10-08T06:55:07Z
dc.identifier.issn00223263en_US
dc.identifier.doi10.1021/jo9021919en_AU
dc.identifier.urihttp://hdl.handle.net/10072/33626
dc.description.abstractThe pyranose scaffold is unique in its ability to position pharmacophore substituents in various ways in 3D space, and unique pharmacophore scanning libraries could be envisaged that focus on scanning topography rather than diversity in the type of substituents. Approaches have been described that make use of amine and acid functionalities on the pyranose scaffolds to append substituents, and this has enabled the generation of libraries of significant structural diversity. Our general aim was to generate libraries of pyranose-based drug-like mimetics, where the substituents are held close to the scaffold, in order to obtain molecules with better defined positions for the pharmacophore substituents. Here we describe the development of a versatile synthetic route toward peptide mimetics build on 2-amino pyranose scaffolds. The method allows introduction of a wide range of substituent types, it is regio- and stereospecific, and the later diversity steps are performed on solid phase. Further, the same process was applied on glucose and allose scaffolds, in the exemplified cases, and is likely adaptable to other pyranose building blocks. The methods developed in this work give access to molecules that position the three selected binding elements in various 3D orientations on a pyranose scaffold and have been applied for the production of a systematically diverse library of several hundred monosaccharide-based mimetics.en_US
dc.description.peerreviewedYesen_US
dc.description.publicationstatusYesen_AU
dc.languageEnglishen_US
dc.language.isoen_AU
dc.publisherAmerican Chemical Societyen_US
dc.publisher.placeUnited Statesen_US
dc.relation.ispartofstudentpublicationNen_AU
dc.relation.ispartofpagefrom197en_US
dc.relation.ispartofpageto203en_US
dc.relation.ispartofissue1en_US
dc.relation.ispartofjournalJournal of Organic Chemistryen_US
dc.relation.ispartofvolume75en_US
dc.rights.retentionYen_AU
dc.subject.fieldofresearchMedicinal and Biomolecular Chemistry not elsewhere classifieden_US
dc.subject.fieldofresearchOrganic Chemical Synthesisen_US
dc.subject.fieldofresearchcode030499en_US
dc.subject.fieldofresearchcode030503en_US
dc.titleA Versatile Synthetic Approach toward Diversity Libraries using Monosaccharide Scaffoldsen_US
dc.typeJournal articleen_US
dc.type.descriptionC1 - Peer Reviewed (HERDC)en_US
dc.type.codeC - Journal Articlesen_US
gro.date.issued2010
gro.hasfulltextNo Full Text


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