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Labisch, Oliver (2006): Offenkettige Monosaccharide als Liganden. Dissertation, LMU München: Faculty of Chemistry and Pharmacy
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Abstract

In this thesis novel carbohydrate transition metal complexes are presented. As transition metals rhenium(V), copper(II) and palladium(II) are used, and their complexation behaviour towards carbohydrates is investigated. Various carbohydrates, such as tartaric acid, xylaric acid, polyols, hydroxyaldehydes, glyceraldehyde, erythrulose, erythrose, threose and xylose act as ligands in these coordination compounds. The complexes are synthesised and characterised by NMR spectroscopy and single crystal X-ray diffraction. Heteroleptic complexes of copper(II) with xylaric acid and tartaric acid are synthesised and characterised. Different ancillary ligands such as bpma and tpa are used. In these structures the coordination number of copper(II) varies from 4 to 6, and different geometries depending on the ancillary ligand are observed. At last the reactivity of palladium(II) towards highly reducing sugars and aldehydes such as D-erythrose, D-threose, D-erythrulose, D-glyceraldehyde, glyoxal and glycolaldehyde is investigated. Complexes of the hydrated aldehydes can be observed in solution, with the hydrate coordinating up to two metal centers. For the first time complexes of monosaccharides in their open chain form can be identified and characterised in solution. These forms are stabilised and enriched in solution by palladium(II). The crystal structure of a palladium(II)-erythrose complex is presented, which is the first crystal structure of this tetrose as yet.