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dc.contributor.authorLe Thanh, Giang
dc.contributor.authorAbbenante, Giovanni
dc.contributor.authorAdamson, George
dc.contributor.authorBecker, Bernd
dc.contributor.authorClark, Chris
dc.contributor.authorCondie, Glenn
dc.contributor.authorFalzun, Tania
dc.contributor.authorGrathwohl, Matthias
dc.contributor.authorGupta, Praveer
dc.contributor.authorHanson, Michael
dc.contributor.authorHuynh, Ngoc
dc.contributor.authorKatavic, Peter
dc.contributor.authorKuipers, Krystle
dc.contributor.authorLam, Ann
dc.contributor.authorLiu, Ligong
dc.contributor.authorMann, Maretta
dc.contributor.authorMason, Jeff
dc.contributor.authorMcKeveney, Declan
dc.contributor.authorMuldoon, Craig
dc.contributor.authorPearson, Andrew
dc.contributor.authorRajaratnam, Premraj
dc.contributor.authorRyan, Sarah
dc.contributor.authorTornetzki, Gerry
dc.contributor.authorVerquin, Geraldine
dc.contributor.authorWaanders, Jennifer
dc.contributor.authorWest, Michael
dc.contributor.authorWilcox, Neil
dc.contributor.authorWimmer, Norbert
dc.contributor.authorYau, Annika
dc.contributor.authorZuegg, Johannes
dc.contributor.authorMeutermans, Wim
dc.contributor.editorC. Dale Poulters
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.
dc.publisherAmerican Chemical Society
dc.publisher.placeUnited States
dc.relation.ispartofjournalJournal of Organic Chemistry
dc.subject.fieldofresearchMedicinal and biomolecular chemistry
dc.subject.fieldofresearchOrganic chemistry
dc.subject.fieldofresearchOrganic chemical synthesis
dc.titleA Versatile Synthetic Approach toward Diversity Libraries using Monosaccharide Scaffolds
dc.typeJournal article
dc.type.descriptionC1 - Articles
dc.type.codeC - Journal Articles
gro.hasfulltextNo Full Text
gro.griffith.authorPearson, Andrew G.

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