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dc.contributor.authorLam, Cary F. C.
dc.contributor.authorGrkovic, Tanja
dc.contributor.authorNorrie Pearce, A.
dc.contributor.authorCopp, Brent R.
dc.date.accessioned2017-05-03T15:59:43Z
dc.date.available2017-05-03T15:59:43Z
dc.date.issued2012
dc.date.modified2013-06-17T23:50:54Z
dc.identifier.issn14770520
dc.identifier.doi10.1039/c2ob07090a
dc.identifier.urihttp://hdl.handle.net/10072/48700
dc.description.abstractThe mechanisms of action of the cytotoxic marine pyrroloiminoquinone alkaloids the discorhabdins are unknown. We have determined that discorhabdin B acts as an electrophile towards biomimetic thiol nucleophiles leading to debrominated adducts. In contrast, less potent cytotoxins discorhabdins D and Q failed to react, supporting an SAR model of cytotoxicity requiring an orchestrated combination of an electrophilic ?1 carbon centre and a nucleophilic N-18 amine for potent activity. The stereospecific nature of nucleophile trapping exhibited by both enantiomers of discorhabdin B implies the biogenesis of ovothiol A substituted discorhabdins H, H2, K and K2 need not be mediated by enzymatic processes.
dc.description.peerreviewedYes
dc.description.publicationstatusYes
dc.languageEnglish
dc.language.isoeng
dc.publisherRSC Publishing
dc.publisher.placeUnited Kingdom
dc.relation.ispartofstudentpublicationN
dc.relation.ispartofpagefrom3092
dc.relation.ispartofpageto3097
dc.relation.ispartofissue15
dc.relation.ispartofjournalOrganic and Biomolecular Chemistry
dc.relation.ispartofvolume10
dc.rights.retentionY
dc.subject.fieldofresearchNatural Products Chemistry
dc.subject.fieldofresearchMedicinal and Biomolecular Chemistry
dc.subject.fieldofresearchOrganic Chemistry
dc.subject.fieldofresearchcode030502
dc.subject.fieldofresearchcode0304
dc.subject.fieldofresearchcode0305
dc.titleInvestigation of the electrophilic reactivity of the cytotoxic marine alkaloid discorhabdin B
dc.typeJournal article
dc.type.descriptionC1 - Articles
dc.type.codeC - Journal Articles
gro.date.issued2012
gro.hasfulltextNo Full Text
gro.griffith.authorGrkovic, Tanja


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