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Updated: Oct 3, 2026

Amide Coupling Reaction for the Synthesis of Bispyridine-based Ligands and Their Complexation to Platinum as Dinuclear Anticancer Agents
Published on: May 28, 2014
The First Platinum(IV) Complexes with Glucopyranoside Ligands. A New Coordination Mode of Carbohydrates
Henrik Junicke1, Clemens Bruhn, Dieter Ströhl
1Institut für Anorganische Chemie und Institut für Organische Chemie, Martin-Luther-Universität Halle-Wittenberg, Kurt-Mothes Strasse 2, D-06120 Halle/Saale, Germany.
Abstract:
[(PtMe(3)I)(4)] reacts with AgBF(4) in acetone to give fac-[PtMe(3)(Me(2)CO)(3)]BF(4) (2) which was isolated as strongly moisture and air sensitive, colorless crystals and characterized by microanalysis and NMR spectroscopy ((1)H, (13)C, (195)Pt). The X-ray structure analysis (orthorhombic, Pcab, a = 15.599(3) Å, b = 15.685(2) Å, c = 15.763(3) Å, Z = 8) reveals that 2 is monomeric and that the cation exhibits local C(3)(v)() symmetry. The reaction of 2 with glucopyranoses (1,6-anhydro-beta-D-glucopyranose (3a), 1-methyl-alpha-D-glucopyranoside (3b), and 1-phenyl-beta-D-glucopyranoside (3c)) yields carbohydrate complexes [PtMe(3)L]BF(4) (4a-4c, L = 3a-3c). The complexes were characterized by microanalysis, ESI mass spectrometry and by NMR spectroscopy ((1)H, (13)C, (195)Pt) displaying that the carbohydrates act as tridentate chelating ligands coordinated by the hydroxyl groups 2-OH and 4-OH and by the acetal oxygen atom of the pyranose ring. This structure was also confirmed by X-ray structure analysis of 4a (orthorhombic, P2(1)2(1)2(1), a = 6.404(1) Å, b = 8.636(2) Å, c = 27.161(5) Å, Z = 4). The cyclic system of the two five-membered and the one six-membered 1,3,2-dioxaplatina rings is not free from angle strain; two O-Pt-O angles are distinctly smaller than 90 degrees (O2-Pt-O5 73.6(2), O4-Pt-O5 75.6(2) degrees ). The Pt-O bond to the acetal oxygen atom in the pyranose ring is significantly longer (Pt-O5 2.288(5) Å) than the two Pt-OH bonds (Pt-O2 2.246(5), Pt-O4 2.248(4) and belongs to the longest Pt-O bonds at all.
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Stereoisomerism
Isomers are different chemical species that have the same chemical formula.
Transition metal complexes often exist as geometric isomers, in which the same atoms are connected through the same types of bonds but with differences in their orientation in space. Coordination complexes with two different ligands in the cis and trans positions from a ligand of interest form isomers. For example, the octahedral [Co(NH3)4Cl2]+ ion has two isomers (Figure 1) In the cis...