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Reactions of Co(III)-coordinated Ornithine: Towards Inhibitors of the Polyamine Biosynthetic Pathway
Andrea J.
Clarkson A,
Allan G.
Blackman A D,
Charles R.
Clark A,
Alan M.
Sargeson B C
A
Department of Chemistry, University of Otago, PO Box 56, Dunedin, New Zealand.
B
Research School of Chemistry, Australian National University, Canberra, ACT 0200, Australia.
C
Deceased.
D
Corresponding author. Email: blackman@chemistry.otago.ac.nz
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Australian Journal of Chemistry 62(10) 1221–1225 http://dx.doi.org/10.1071/CH09315
Submitted: 2 June 2009
Accepted: 28 July 2009
Published online: 13 October 2009
Abstract
Treatment of the complex Δ,Λ-[Co(en)2(S-ornithineH-κ2N,O)](CF3SO3)3 with SOCl2 in DMF gives a mixture of the expected imino complex [Co(en)2(2-iminoornithineH-κ2N,O)]3+ and the amidine complex [Co(en)2(5-{[(1E)-(dimethylamino)methylene]amino}-2-iminopentanoate-κ2N,O)]3+, which is proposed to result from the reaction of the Vilsmeier reagent [ClCH=N(CH3)2]+ with the terminal amine of coordinated ornithine. Treatment of the imino complex with nitromethane in alkaline solution gives the complex [Co(en)2(2-nitromethylornithineH-κ2N,O)]3+, which contains the potential suicide inhibitor 2-nitromethylornithine. X-ray crystal structures of Δ-[Co(en)2(S-ornithineH-κ2N,O)]Br3 and Δ,Λ-[Co(en)2(5-{[(1E)-(dimethylamino)methylene]amino}-2-iminopentanoate-κ2N,O)](ClO4)3 are reported.
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