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http://dx.doi.org/10.18419/opus-1124
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DC Element | Wert | Sprache |
---|---|---|
dc.contributor.author | Straub, Alexander | de |
dc.contributor.author | Effenberger, Franz | de |
dc.contributor.author | Fischer, Peter | de |
dc.date.accessioned | 2009-08-27 | de |
dc.date.accessioned | 2016-03-31T07:47:42Z | - |
dc.date.available | 2009-08-27 | de |
dc.date.available | 2016-03-31T07:47:42Z | - |
dc.date.issued | 1990 | de |
dc.identifier.other | 312085257 | de |
dc.identifier.uri | http://nbn-resolving.de/urn:nbn:de:bsz:93-opus-43710 | de |
dc.identifier.uri | http://elib.uni-stuttgart.de/handle/11682/1141 | - |
dc.identifier.uri | http://dx.doi.org/10.18419/opus-1124 | - |
dc.description.abstract | Rabbit muscle aldolase was found to catalyze stereoselective aldol addition of dihydroxyacetone phosphate (1) to 3-azido-2-hydroxypropana(2 ). The ketose 1-phosphates were isolated as barium salts, 4a/4b, and hydrolyzed with acid phosphatase. The mixture of 6-azido-6-deoxy-D-fructose(5) and 6-azido-6-deoxy-L-sorbose thus obtained was separated by anion-exchange chromatography. Reductive amination of 5 and 6 yielded, respectively, 1-deoxymannojirimycin (7) and 1-deoxynojirimycin (8), with high diastereoselectivity (>98:2). Analogous aldol addition of 1 to 3-azido-2-hydroxybutanal( 9)( E:Z = 92:8) afforded a mixture of the 6-azido-6,7-dideoxyheptuloses 12 and 13, which contained 88% of 6-azido-6,7-dideoxy-D-altro-heptulose(13 ). After anion-exchange chromatography, 13 was isolated as a 18:82 mixture of the β/α anomers. Reductive amination of pure 13 gave a mixture of 2,6,7-trideoxy-2,6-imino-D-glycero-D-manno and D-gluco-heptitol (14 and 15) (3:2 molar ratio), which likewise was separated by anion-exchange chromatography. If a mixture of 12 and 13 was hydrogenated under identical conditions, 2,6,7-trideoxy-2,6-imino-L-glycero-L-gulo-heptitol(16) could be isolated besides 14 and 15. | en |
dc.language.iso | en | de |
dc.rights | info:eu-repo/semantics/openAccess | de |
dc.subject.classification | Enzymkatalyse , Aldolasen | de |
dc.subject.ddc | 540 | de |
dc.title | Aldolase-catalyzed C-C bond formation for stereoselective synthesis of nitrogen-containing carbohydrates | en |
dc.type | article | de |
ubs.fakultaet | Fakultät Chemie | de |
ubs.institut | Institut für Organische Chemie | de |
ubs.opusid | 4371 | de |
ubs.publikation.source | Journal of Organic Chemistry 55 (1990), S. 3926-3932. URL http://dx.doi.org./10.1021/jo00299a043 | de |
ubs.publikation.typ | Zeitschriftenartikel | de |
Enthalten in den Sammlungen: | 03 Fakultät Chemie |
Dateien zu dieser Ressource:
Datei | Beschreibung | Größe | Format | |
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eff199.pdf | 902,37 kB | Adobe PDF | Öffnen/Anzeigen |
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