Total Synthesis of Microcystin-LF and Derivatives Thereof

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ZEMSKOV, Ivan, Stefan ALTANER, Daniel R. DIETRICH, Valentin WITTMANN, 2017. Total Synthesis of Microcystin-LF and Derivatives Thereof. In: The Journal of Organic Chemistry. 82(7), pp. 3680-3691. ISSN 0022-3263. eISSN 1520-6904. Available under: doi: 10.1021/acs.joc.7b00175

@article{Zemskov2017-04-07Total-38859, title={Total Synthesis of Microcystin-LF and Derivatives Thereof}, year={2017}, doi={10.1021/acs.joc.7b00175}, number={7}, volume={82}, issn={0022-3263}, journal={The Journal of Organic Chemistry}, pages={3680--3691}, author={Zemskov, Ivan and Altaner, Stefan and Dietrich, Daniel R. and Wittmann, Valentin} }

<rdf:RDF xmlns:dcterms="" xmlns:dc="" xmlns:rdf="" xmlns:bibo="" xmlns:dspace="" xmlns:foaf="" xmlns:void="" xmlns:xsd="" > <rdf:Description rdf:about=""> <dcterms:issued>2017-04-07</dcterms:issued> <dcterms:rights rdf:resource=""/> <dspace:isPartOfCollection rdf:resource=""/> <dcterms:available rdf:datatype="">2017-05-12T11:26:58Z</dcterms:available> <void:sparqlEndpoint rdf:resource="http://localhost/fuseki/dspace/sparql"/> <dspace:isPartOfCollection rdf:resource=""/> <dc:contributor>Zemskov, Ivan</dc:contributor> <dc:creator>Altaner, Stefan</dc:creator> <dcterms:abstract xml:lang="eng">Microcystins (MCs) are highly toxic natural products which are produced by cyanobacteria. They can be released to the water during harmful algal blooms and are a serious threat to animals and humans. Described is the total synthesis of the cyanotoxin microcystin-LF (MC-LF, 1a) and two derivatives thereof. Deuterated derivative 1b is of interest as an internal standard during MC quantification in biological samples by mass spectrometry and alkyne-labeled 1c can be employed for toxin derivatization by click chemistry with an azide-containing reporter molecule or as an activity-based probe to identify interaction partners. Application of tert-butyl ester protecting groups for erythro-β-d-methylaspartic acid and γ-d-glutamic acid were key for an isomerization-free synthesis. The analytical data of synthetic MC-LF were identical to those of an authentic sample of the natural product. All derivatives 1a-c were determined to be potent inhibitors of protein phosphatase-1 with similar activity.</dcterms:abstract> <dspace:hasBitstream rdf:resource=""/> <dc:date rdf:datatype="">2017-05-12T11:26:58Z</dc:date> <foaf:homepage rdf:resource="http://localhost:8080/jspui"/> <dcterms:title>Total Synthesis of Microcystin-LF and Derivatives Thereof</dcterms:title> <dc:language>eng</dc:language> <dcterms:hasPart rdf:resource=""/> <dcterms:isPartOf rdf:resource=""/> <dc:contributor>Dietrich, Daniel R.</dc:contributor> <dc:rights>terms-of-use</dc:rights> <bibo:uri rdf:resource=""/> <dc:creator>Wittmann, Valentin</dc:creator> <dcterms:isPartOf rdf:resource=""/> <dc:creator>Zemskov, Ivan</dc:creator> <dc:creator>Dietrich, Daniel R.</dc:creator> <dc:contributor>Altaner, Stefan</dc:contributor> <dc:contributor>Wittmann, Valentin</dc:contributor> </rdf:Description> </rdf:RDF>

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