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Orthogonally Protected Furanoid Sugar Diamino Acids for Solid-Phase Synthesis of Oligosaccharide Mimetics

Orthogonally Protected Furanoid Sugar Diamino Acids for Solid-Phase Synthesis of Oligosaccharide Mimetics

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JOHN, Franklin, Valentin WITTMANN, 2015. Orthogonally Protected Furanoid Sugar Diamino Acids for Solid-Phase Synthesis of Oligosaccharide Mimetics. In: The Journal of Organic Chemistry. 80(15), pp. 7477-7485. ISSN 0022-3263. eISSN 1520-6904

@article{John2015-08-07Ortho-32331, title={Orthogonally Protected Furanoid Sugar Diamino Acids for Solid-Phase Synthesis of Oligosaccharide Mimetics}, year={2015}, doi={10.1021/acs.joc.5b01049}, number={15}, volume={80}, issn={0022-3263}, journal={The Journal of Organic Chemistry}, pages={7477--7485}, author={John, Franklin and Wittmann, Valentin} }

<rdf:RDF xmlns:rdf="http://www.w3.org/1999/02/22-rdf-syntax-ns#" xmlns:bibo="http://purl.org/ontology/bibo/" xmlns:dc="http://purl.org/dc/elements/1.1/" xmlns:dcterms="http://purl.org/dc/terms/" xmlns:xsd="http://www.w3.org/2001/XMLSchema#" > <rdf:Description rdf:about="https://kops.uni-konstanz.de/rdf/resource/123456789/32331"> <dc:contributor>John, Franklin</dc:contributor> <dc:language>eng</dc:language> <dcterms:abstract xml:lang="eng">Sugar diamino acids (SDAs), which differ from the widely used sugar amino acids in the presence of a second amino group connected to the carbohydrate core, share structural features of both amino acids and carbohydrates. They can be used for the preparation of linear and branched amide-linked oligosaccharide mimetics. Such oligomers carry free amino groups, which are positively charged at neutral pH, in a spatially defined way and, thus, represent a potential class of aminoglycoside mimetics. We report here the first examples of orthogonally protected furanoid SDAs and their use in solid-phase synthesis. Starting from d-glucose, we developed a divergent synthetic route to three derivatives of 3,5-diamino-3,5-dideoxy-d-ribofuranose. These building blocks are compatible with solid-phase peptide synthesis following the 9-fluorenylmethoxycarbonyl (Fmoc) strategy, which we demonstrate by the synthesis of an SDA tetramer.</dcterms:abstract> <dc:creator>John, Franklin</dc:creator> <dc:creator>Wittmann, Valentin</dc:creator> <dc:contributor>Wittmann, Valentin</dc:contributor> <dcterms:issued>2015-08-07</dcterms:issued> <dcterms:title>Orthogonally Protected Furanoid Sugar Diamino Acids for Solid-Phase Synthesis of Oligosaccharide Mimetics</dcterms:title> <dc:date rdf:datatype="http://www.w3.org/2001/XMLSchema#dateTime">2015-12-03T15:17:55Z</dc:date> <bibo:uri rdf:resource="https://kops.uni-konstanz.de/handle/123456789/32331"/> <dcterms:available rdf:datatype="http://www.w3.org/2001/XMLSchema#dateTime">2015-12-03T15:17:55Z</dcterms:available> </rdf:Description> </rdf:RDF>

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