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Article: Syntheses of dihydroartemisinic acid and dihydro-epi-deoxyarteannuin B incorporating a stable isotope label at the 15-position for studies into the biosynthesis of artemisinin

TitleSyntheses of dihydroartemisinic acid and dihydro-epi-deoxyarteannuin B incorporating a stable isotope label at the 15-position for studies into the biosynthesis of artemisinin
Authors
KeywordsArtemisia annua
Artemisinin
Dihydro-epi-deoxyarteanuin B
Dihydroartemisinic acid
Isotopic labeling
Issue Date2001
PublisherPergamon. The Journal's web site is located at http://www.elsevier.com/locate/tet
Citation
Tetrahedron, 2001, v. 57 n. 40, p. 8495-8510 How to Cite?
Abstract[15-13C2H3]-Dihydroartemisinic acid (3a) and [15-13CH3]-dihydro-epi-deoxyarteannuin B (7b), intended for evaluation in vivo as biosynthetic precursors to artemisinin, have been obtained from a reconstructive synthesis. The decalenone acid 8 from acid degradation of artemisinin (1) serves as a common intermediate: following addition of labeled methyl Grignard reagent to 8, either labeled precursor can be prepared in good yield by varying the work-up conditions employed. It is shown that both compounds are prone to autoxidation on storage and that the products of such oxidation and subsequent rearrangement reactions might be confused with bona fide metabolites when using these labeled precursors in feeding experiments designed to determine the biosynthetic route to artemisinin in Artemisia annua. © 2001 Elsevier Science Ltd. All rights reserved.
Persistent Identifierhttp://hdl.handle.net/10722/68961
ISSN
2015 Impact Factor: 2.645
2015 SCImago Journal Rankings: 0.991
ISI Accession Number ID
References

 

DC FieldValueLanguage
dc.contributor.authorSy, LKen_HK
dc.contributor.authorZhu, NYen_HK
dc.contributor.authorBrown, GDen_HK
dc.date.accessioned2010-09-06T06:09:17Z-
dc.date.available2010-09-06T06:09:17Z-
dc.date.issued2001en_HK
dc.identifier.citationTetrahedron, 2001, v. 57 n. 40, p. 8495-8510en_HK
dc.identifier.issn0040-4020en_HK
dc.identifier.urihttp://hdl.handle.net/10722/68961-
dc.description.abstract[15-13C2H3]-Dihydroartemisinic acid (3a) and [15-13CH3]-dihydro-epi-deoxyarteannuin B (7b), intended for evaluation in vivo as biosynthetic precursors to artemisinin, have been obtained from a reconstructive synthesis. The decalenone acid 8 from acid degradation of artemisinin (1) serves as a common intermediate: following addition of labeled methyl Grignard reagent to 8, either labeled precursor can be prepared in good yield by varying the work-up conditions employed. It is shown that both compounds are prone to autoxidation on storage and that the products of such oxidation and subsequent rearrangement reactions might be confused with bona fide metabolites when using these labeled precursors in feeding experiments designed to determine the biosynthetic route to artemisinin in Artemisia annua. © 2001 Elsevier Science Ltd. All rights reserved.en_HK
dc.languageengen_HK
dc.publisherPergamon. The Journal's web site is located at http://www.elsevier.com/locate/teten_HK
dc.relation.ispartofTetrahedronen_HK
dc.subjectArtemisia annuaen_HK
dc.subjectArtemisininen_HK
dc.subjectDihydro-epi-deoxyarteanuin Ben_HK
dc.subjectDihydroartemisinic aciden_HK
dc.subjectIsotopic labelingen_HK
dc.titleSyntheses of dihydroartemisinic acid and dihydro-epi-deoxyarteannuin B incorporating a stable isotope label at the 15-position for studies into the biosynthesis of artemisininen_HK
dc.typeArticleen_HK
dc.identifier.openurlhttp://library.hku.hk:4550/resserv?sid=HKU:IR&issn=0040-4020&volume=57&spage=8495&epage=8510&date=2001&atitle=Syntheses+of+dihydroartemisinic+acid+and+dihydro-epi-deoxyarteannuin+B+incorporating+a+stable+isotope+label+at+the+15-position+for+studies+into+the+biosynthesis+of+artemisininen_HK
dc.identifier.emailSy, LK: sylk@hku.hken_HK
dc.identifier.emailZhu, NY: nzhu@hkucc.hku.hken_HK
dc.identifier.authoritySy, LK=rp00784en_HK
dc.identifier.authorityZhu, NY=rp00845en_HK
dc.description.naturelink_to_subscribed_fulltext-
dc.identifier.doi10.1016/S0040-4020(01)00711-6en_HK
dc.identifier.scopuseid_2-s2.0-0035478434en_HK
dc.identifier.hkuros68644en_HK
dc.relation.referenceshttp://www.scopus.com/mlt/select.url?eid=2-s2.0-0035478434&selection=ref&src=s&origin=recordpageen_HK
dc.identifier.volume57en_HK
dc.identifier.issue40en_HK
dc.identifier.spage8495en_HK
dc.identifier.epage8510en_HK
dc.identifier.isiWOS:000171327500009-
dc.publisher.placeUnited Kingdomen_HK
dc.identifier.scopusauthoridSy, LK=35874602700en_HK
dc.identifier.scopusauthoridZhu, NY=7201449530en_HK
dc.identifier.scopusauthoridBrown, GD=7406468149en_HK

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