1H-Tetrazole as Catalyst in Phosphomorpholidate Coupling Reactions : Efficient Synthesis of GDP-Fucose, GDP-Mannose, and UDP-Galactose
| Publikationstyp: | Zeitschriftenartikel |
| URI (zitierfähiger Link): | http://nbn-resolving.de/urn:nbn:de:bsz:352-opus-44085 |
| Autor/innen: | Wittmann, Valentin; Wong, Chi-Huey |
| Erscheinungsjahr: | 1997 |
| Erschienen in: | The Journal of Organic Chemistry ; 62 (1997), 7. - S. 2144-2147. - ISSN 0022-3263. - eISSN 1520-6904 |
| DOI (zitierfähiger Link): | https://dx.doi.org/10.1021/jo9620066 |
| Zusammenfassung: |
An improved procedure is described for the efficient and high-yield (76-91%) synthesis of nucleoside diphosphate sugars from the readily available nucleoside 5'-monophosphomorpholidate and sugar 1-phosphate in the presence of 1H-tetrazole. Comparative kinetic investigations by means of (31)P NMR spectroscopy with different additives (1,2,4-triazole, acetic acid, N-hydroxysuccinimide, 4-(dimethylamino)pyridine hydrochloride, perchloric acid) and mass spectrometric analysis suggest that tetrazole acts as an acid and as a nucleophilic catalyst in the pyrophosphate bond formation.
|
| Fachgebiet (DDC): | 540 Chemie |
| Link zur Lizenz: | Nutzungsbedingungen |
Zitieren
Dateien zu dieser Ressource
![[PDF]](/themes/Kops/images/mimes/pdf.png "PDF file"){kind=small}
WITTMANN, Valentin, Chi-Huey WONG, 1997. 1H-Tetrazole as Catalyst in Phosphomorpholidate Coupling Reactions : Efficient Synthesis of GDP-Fucose, GDP-Mannose, and UDP-Galactose. In: The Journal of Organic Chemistry. 62(7), pp. 2144-2147. ISSN 0022-3263. eISSN 1520-6904. Available under: doi: 10.1021/jo9620066
@article{Wittmann19971HTet-9975, title={1H-Tetrazole as Catalyst in Phosphomorpholidate Coupling Reactions : Efficient Synthesis of GDP-Fucose, GDP-Mannose, and UDP-Galactose}, year={1997}, doi={10.1021/jo9620066}, number={7}, volume={62}, issn={0022-3263}, journal={The Journal of Organic Chemistry}, pages={2144--2147}, author={Wittmann, Valentin and Wong, Chi-Huey} }
<rdf:RDF xmlns:dcterms="http://purl.org/dc/terms/" xmlns:dc="http://purl.org/dc/elements/1.1/" xmlns:rdf="http://www.w3.org/1999/02/22-rdf-syntax-ns#" xmlns:bibo="http://purl.org/ontology/bibo/" xmlns:dspace="http://digital-repositories.org/ontologies/dspace/0.1.0#" xmlns:foaf="http://xmlns.com/foaf/0.1/" xmlns:void="http://rdfs.org/ns/void#" xmlns:xsd="http://www.w3.org/2001/XMLSchema#" > <rdf:Description rdf:about="https://kops.uni-konstanz.de/rdf/resource/123456789/9975"> <dspace:isPartOfCollection rdf:resource="https://kops.uni-konstanz.de/rdf/resource/123456789/29"/> <dspace:hasBitstream rdf:resource="https://kops.uni-konstanz.de/bitstream/123456789/9975/1/1H_Tetrazole_as_Catalyst_in_Phosphomorpholidate.pdf"/> <dcterms:abstract xml:lang="eng">An improved procedure is described for the efficient and high-yield (76-91%) synthesis of nucleoside diphosphate sugars from the readily available nucleoside 5'-monophosphomorpholidate and sugar 1-phosphate in the presence of 1H-tetrazole. Comparative kinetic investigations by means of (31)P NMR spectroscopy with different additives (1,2,4-triazole, acetic acid, N-hydroxysuccinimide, 4-(dimethylamino)pyridine hydrochloride, perchloric acid) and mass spectrometric analysis suggest that tetrazole acts as an acid and as a nucleophilic catalyst in the pyrophosphate bond formation.</dcterms:abstract> <void:sparqlEndpoint rdf:resource="http://localhost/fuseki/dspace/sparql"/> <dcterms:bibliographicCitation>First publ. in: The Journal of Organic Chemistry ; 62 (1997). - S. 2144-2147</dcterms:bibliographicCitation> <dcterms:rights rdf:resource="https://creativecommons.org/licenses/by-nc-nd/2.0/legalcode"/> <dc:format>application/pdf</dc:format> <foaf:homepage rdf:resource="http://localhost:8080/jspui"/> <dc:date rdf:datatype="http://www.w3.org/2001/XMLSchema#dateTime">2011-03-24T18:15:41Z</dc:date> <dcterms:issued>1997</dcterms:issued> <bibo:uri rdf:resource="http://kops.uni-konstanz.de/handle/123456789/9975"/> <dc:contributor>Wong, Chi-Huey</dc:contributor> <dcterms:hasPart rdf:resource="https://kops.uni-konstanz.de/bitstream/123456789/9975/1/1H_Tetrazole_as_Catalyst_in_Phosphomorpholidate.pdf"/> <dc:creator>Wong, Chi-Huey</dc:creator> <dcterms:isPartOf rdf:resource="https://kops.uni-konstanz.de/rdf/resource/123456789/29"/> <dcterms:title>1H-Tetrazole as Catalyst in Phosphomorpholidate Coupling Reactions : Efficient Synthesis of GDP-Fucose, GDP-Mannose, and UDP-Galactose</dcterms:title> <dc:contributor>Wittmann, Valentin</dc:contributor> <dc:language>eng</dc:language> <dc:creator>Wittmann, Valentin</dc:creator> <dc:rights>terms-of-use</dc:rights> </rdf:Description> </rdf:RDF>
Dateiabrufe seit 01.10.2014 (Informationen über die Zugriffsstatistik)
| 1H_Tetrazole_as_Catalyst_in_Phosphomorpholidate.pdf | 425 |
Das Dokument erscheint in:
Solange nicht anders angezeigt, wird die Lizenz wie folgt beschrieben: terms-of-use
KOPS Suche
Stöbern
Mein Benutzerkonto
