dc.contributor.author | Lam, Cary F. C. | |
dc.contributor.author | Grkovic, Tanja | |
dc.contributor.author | Norrie Pearce, A. | |
dc.contributor.author | Copp, Brent R. | |
dc.date.accessioned | 2017-05-03T15:59:43Z | |
dc.date.available | 2017-05-03T15:59:43Z | |
dc.date.issued | 2012 | |
dc.date.modified | 2013-06-17T23:50:54Z | |
dc.identifier.issn | 14770520 | |
dc.identifier.doi | 10.1039/c2ob07090a | |
dc.identifier.uri | http://hdl.handle.net/10072/48700 | |
dc.description.abstract | The 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.peerreviewed | Yes | |
dc.description.publicationstatus | Yes | |
dc.language | English | |
dc.language.iso | eng | |
dc.publisher | RSC Publishing | |
dc.publisher.place | United Kingdom | |
dc.relation.ispartofstudentpublication | N | |
dc.relation.ispartofpagefrom | 3092 | |
dc.relation.ispartofpageto | 3097 | |
dc.relation.ispartofissue | 15 | |
dc.relation.ispartofjournal | Organic and Biomolecular Chemistry | |
dc.relation.ispartofvolume | 10 | |
dc.rights.retention | Y | |
dc.subject.fieldofresearch | Natural Products Chemistry | |
dc.subject.fieldofresearch | Medicinal and Biomolecular Chemistry | |
dc.subject.fieldofresearch | Organic Chemistry | |
dc.subject.fieldofresearchcode | 030502 | |
dc.subject.fieldofresearchcode | 0304 | |
dc.subject.fieldofresearchcode | 0305 | |
dc.title | Investigation of the electrophilic reactivity of the cytotoxic marine alkaloid discorhabdin B | |
dc.type | Journal article | |
dc.type.description | C1 - Articles | |
dc.type.code | C - Journal Articles | |
gro.date.issued | 2012 | |
gro.hasfulltext | No Full Text | |
gro.griffith.author | Grkovic, Tanja | |