N-Glycoside Complexes of Nickel(ii); Probing Carbohydrate–Transition Metal Interactions

Dale Jones; Marcelis van Holst; Shigenobu Yano; Tomoaki Tanase; Janice Aldrich-Wright

doi:10.1071/CH08349

RESEARCH ARTICLE

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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 and Janice Aldrich-Wright ^A ^C

+ Author Affiliations

- Author Affiliations

^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

Australian Journal of Chemistry 62(3) 265-268 https://doi.org/10.1071/CH08349
Submitted: 14 August 2008 Accepted: 7 January 2009 Published: 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.

Acknowledgements

The support of the University of Western Sydney Research Grant Scheme is gratefully acknowledged. M. van Holst would like to thank the College of Health Sciences for its generous support through a writing fellowship. We thank Mr B. Foster (James Cook University) for performing the microanalyses.

References

N-Glycoside Complexes of Nickel(ii); Probing Carbohydrate–Transition Metal Interactions

Abstract

Acknowledgements

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