0000000001316271

AUTHOR

Tobias Wunberg

showing 5 related works from this author

Combinatorial solid-phase synthesis using D-galactose as a chiral five-dimension-deversity scaffold

1999

Abstract All five hydroxy groups of galactose as the scaffold are used for selective coupling of side chains in a combinatorial methodology by application of a set of orthogonally stable protecting groups in combination with a thioglycoside anchor.

Scaffoldchemistry.chemical_compoundSolid-phase synthesisStereochemistryChemistryGalactoseOrganic ChemistryDrug DiscoveryDimension (graph theory)Side chainBiochemistryCombinatorial chemistryTetrahedron Letters
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d-Glucose as a multivalent chiral scaffold for combinatorial chemistry

2002

Due to their high density of functional groups and their availability in a variety of diastereomeric forms, monosaccharides are considered attractive scaffolds for combinatorial chemistry that allow the attachment and defined spatial alignment of up to five different pharmacophoric groups. For their application in combinatorial syntheses on solid phase, a set of selectively removable hydroxy protecting groups in combination with a cleavable anchor is required. Herein, we report on the construction and use of a versatile multivalent glucose building block for parallel synthesis on the solid phase.

chemistry.chemical_classificationSpectrometry Mass Electrospray IonizationScaffoldAlkylationMolecular StructureStereochemistryOrganic ChemistryDiastereomerHigh densityGeneral MedicineCrystallography X-RayBiochemistryCombinatorial chemistryAnalytical Chemistrychemistry.chemical_compoundCross-Linking ReagentsGlucosechemistryThioglycosidesD-GlucoseCombinatorial Chemistry TechniquesMonosaccharideChromatography High Pressure LiquidCarbohydrate Research
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Combinatorial synthesis of amino acid- and peptide-carbohydrate conjugates on solid phase

2004

Carbohydrates are useful polyfunctional scaffold molecules which allow the selective attachment of a number of different side chains. The combinatorial solid phase synthesis of diverse amino acid or peptide conjugates of a polyfunctional glucose scaffold based on a set of selectively removable and orthogonally stable protecting groups is described. The resulting carbohydrate-peptide hybrids constitute potential turn mimetics.

chemistry.chemical_classificationPeptidomimeticOrganic ChemistryPeptideCarbohydrateBiochemistryCombinatorial chemistryAmino acidTurn (biochemistry)Solid-phase synthesischemistryDrug DiscoverySide chainConjugateTetrahedron
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D-Glucose as a Pentavalent Chiral Scaffold

2003

A novel carbohydrate-based scaffold for combinatorial chemistry has been developed. This scaffold allows the selective attachment of five different side chains, giving rise to products of enormous structural diversity. As a demonstration of its usefulness, a series of model compounds has been prepared in high purity and yield by multistep parallel synthesis on a solid phase. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)

Scaffoldchemistry.chemical_compoundSolid-phase synthesisChemistryD-GlucosePeptidomimeticYield (chemistry)Organic ChemistrySide chainStructural diversityOrganic chemistryPhysical and Theoretical ChemistryCombinatorial chemistryEuropean Journal of Organic Chemistry
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CCDC 813647: Experimental Crystal Structure Determination

2017

Related Article: Till Opatz, Christopher Kallus, Tobias Wunberg, Wolfgang Schmidt, Stefan Henke, Horst Kunz|2002|Carbohydr.Res.|337|2089|doi:10.1016/S0008-6215(02)00301-4

Space GroupCrystallographyCrystal SystemCrystal StructureCell Parameters(5-(benzyloxy)-3-(((4-chlorophenyl)carbamoyl)oxy)-6-methoxy-4-propoxytetrahydro-2H-pyran-2-yl)methyl (4-chlorophenyl)carbamateExperimental 3D Coordinates
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