Synthesis of 2-(nitromethyl)ornithine from ornithine mediated by cobalt(III).

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dc.contributor.authorButler, Philip
dc.contributor.authorCrane, Christopher
dc.contributor.authorGolding, Bernard
dc.contributor.authorHammershoi, Anders
dc.contributor.authorHockless, David
dc.contributor.authorPetersen, Tue
dc.contributor.authorSargeson, Alan
dc.contributor.authorWard, Stephen A
dc.date.accessioned2015-12-13T22:22:55Z
dc.date.available2015-12-13T22:22:55Z
dc.date.issued2002
dc.date.updated2015-12-11T08:01:16Z
dc.description.abstractRac.-p-(tris(2-aminoethyl)amine-2-(nitromethyl)ornithine)cobalt(III) trichloride (2d) was obtained by a simple three-step procedure from ornithine using cobalt template chemistry. p-(Tris(2-aminoethyl)amine-ornithine)cobalt(III) trichloride (2a) was obtained from tris(2-aminoethyl)amine (tren) and (S)-ornithine in the presence of cobalt(II), which was oxidised to cobalt(III) during the reaction. Complex 2a was selectively oxidised with thionyl chloride-dimethyl formamide to p-(tris(2-aminoethyl)amine-dehydro-ornithine)cobalt(III) trichloride 2b. Complex 2c, in which reaction of thionyl chloride-dimethyl formamide has also occurred at the δ-amine of ornithine, was obtained at longer reaction times. Complex 2b reacted with nitromethane anion to give rac.-p-(tris(2-aminoethyl)amino-2-(nitromethyl)ornithine)cobalt(III) trichloride (2d). The amino acid rac.-2-(nitromethyl)ornithine (1b) was released by reducing complex 2d with aqueous ammonium sulfide. Complex 2d was expected to release 2-(nitromethyl)ornithine (1b) in hypoxic cells, where the amino acid could act as an inhibitor of ornithine decarboxylase. Preliminary data indicated that complex 2d was weakly cytotoxic in one cell type studied.
dc.identifier.issn0020-1693
dc.identifier.urihttp://hdl.handle.net/1885/72511
dc.publisherElsevier
dc.sourceInorganica Chimica Acta
dc.subjectKeywords: 2 (nitromethyl)ornithine; 2 (nitromethyl)ornithine 2,5 diamino 2 nitromethylpentanoic acid; 4 [tris(2 aminoethyl)amine 2 (nitromethyl)ornithine]cobalt; 4 [tris(2 aminoethyl)amine ornithine]cobalt; 4 [tris(2 aminomethyl)amine dehydro ornithine]cobalt; coba Cobalt complexes; Ornithine; Template chemistry
dc.titleSynthesis of 2-(nitromethyl)ornithine from ornithine mediated by cobalt(III).
dc.typeJournal article
local.bibliographicCitation.lastpage321
local.bibliographicCitation.startpage318
local.contributor.affiliationButler, Philip, Newcastle University
local.contributor.affiliationCrane, Christopher, College of Physical and Mathematical Sciences, ANU
local.contributor.affiliationGolding, Bernard, Newcastle University
local.contributor.affiliationHammershoi, Anders, University of Copenhagen
local.contributor.affiliationHockless, David, College of Physical and Mathematical Sciences, ANU
local.contributor.affiliationPetersen, Tue, University of Copenhagen
local.contributor.affiliationSargeson, Alan, College of Physical and Mathematical Sciences, ANU
local.contributor.affiliationWard, Stephen A, Liverpool School of Tropical Medicine
local.contributor.authoremailu5800192@anu.edu.au
local.contributor.authoruidCrane, Christopher, u930014
local.contributor.authoruidHockless, David, u930167
local.contributor.authoruidSargeson, Alan, u5800192
local.description.notesImported from ARIES
local.description.refereedYes
local.identifier.absfor030503 - Organic Chemical Synthesis
local.identifier.ariespublicationMigratedxPub3284
local.identifier.citationvolume331
local.identifier.doi10.1016/S0020-1693(02)00691-6
local.identifier.scopusID2-s2.0-0037187612
local.identifier.uidSubmittedByMigrated
local.type.statusPublished Version

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