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N-Glycoside Complexes of Nickel(ii); Probing Carbohydrate–Transition Metal Interactions
Dale
Jones A,
Marcelis
van Holst A,
Shigenobu
Yano B,
Tomoaki
Tanase B,
Janice
Aldrich-Wright A C
A
School of Biomedical and Health Sciences, University of Western Sydney, Locked Bag 1797, Penrith South DC, NSW 1797, Australia.
B
Department of Chemistry, Faculty of Science, Nara Women’s University, Nara 630-8506, Japan.
C
Corresponding author. Email: j.aldrich-wright@uws.edu.au
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Australian Journal of Chemistry 62(3) 265–268 http://dx.doi.org/10.1071/CH08349
Submitted: 14 August 2008
Accepted: 7 January 2009
Published online: 20 March 2009
Abstract
Nickel(ii) complexes prepared from d- and l-arabinose (d-ara and l-ara) and 1,2-diaminoethane (en), [Ni(en-d-ara)2](ClO4)2·2H2O 1 and [Ni(en-l-ara)2](ClO4)2·2H2O 2 (where en-d-ara is 1-((2-aminoethyl)amino)-1-deoxy-d-arabinose) were synthesized and characterized by absorption spectroscopy, circular dichroism (CD), and X-ray crystallography. The CD spectra of 1 and 2 in the d–d transition region indicate a C2 chiral configuration around the metal centre. X-ray crystallography of 1 revealed that two 1-((2-aminoethyl)amino)-1-deoxy-d-arabinose ligands coordinate to the nickel atom in nearly C2 symmetry, through the C(2) hydroxy group of the arabinose moiety and two nitrogen atoms of the diamine in a meridional mode. This results in a Λ-C2-helical configuration around the metal centre. The arabinose ring adopts the rare α-1C4 chair conformation and the carbohydrate–chelate ring conformation is δ.
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