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Australian Journal of Chemistry Australian Journal of Chemistry Society
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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 and Alan M. Sargeson B C
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- Author Affiliations

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

Australian Journal of Chemistry 62(10) 1221-1225 https://doi.org/10.1071/CH09315
Submitted: 2 June 2009  Accepted: 28 July 2009   Published: 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.


Acknowledgements

We thank Professor Ward Robinson and Dr Jan Wikaira (University of Canterbury) for X-ray data collection. C.R.C. thanks the University of Otago for granting a period of study leave at the Australian National University and the Sargeson family for their warm hospitality during his stay.


References


[1]   Data from Statistics New Zealand (http://www.nzhis.govt.nz/moh.nsf/pagesns/528/$File/Mortality2004.pdf) and The World Health Organization (http://www.who.int/mediacentre/news/releases/2003/pr27/en/). Accessed 4 September 2009.

[2]   D. C. Ware, W. R. Wilson, W. A. Denny, C. E. F. Rickard, J. Chem. Soc. Chem. Commun. 1991,  1171.
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