Synthesis of d-fructose conjugated ligands via C6 and C1 and their corresponding [Ru(bpy)2(L)]Cl2 complexes

Michael Pröhl; Pascal D Moser; Justyna A Czaplewska; Patrick Hoffmann; Tanja Buś; Anja Traeger; Helmar Goerls; Ulrich S Schubert; Michael Gottschaldt

doi:10.1016/j.carres.2017.04.020

Synthesis of d-fructose conjugated ligands via C6 and C1 and their corresponding [Ru(bpy)₂(L)]Cl₂ complexes

Carbohydr Res. 2017 Jun 29:446-447:19-27. doi: 10.1016/j.carres.2017.04.020. Epub 2017 Apr 27.

Authors

Michael Pröhl¹, Pascal D Moser¹, Justyna A Czaplewska¹, Patrick Hoffmann¹, Tanja Buś¹, Anja Traeger¹, Helmar Goerls², Ulrich S Schubert¹, Michael Gottschaldt³

Affiliations

¹ Laboratory of Organic and Macromolecular Chemistry (IOMC), Friedrich Schiller University Jena, Humboldtstraße 10, 07743 Jena, Germany; Jena Center for Soft Matter (JCSM), Friedrich Schiller University Jena, Philosophenweg 7, 07743 Jena, Germany.
² Institute for Inorganic and Analytical Chemistry, Friedrich Schiller University Jena, Humboldtstraße 8, 07743 Jena, Germany.
³ Laboratory of Organic and Macromolecular Chemistry (IOMC), Friedrich Schiller University Jena, Humboldtstraße 10, 07743 Jena, Germany; Jena Center for Soft Matter (JCSM), Friedrich Schiller University Jena, Philosophenweg 7, 07743 Jena, Germany. Electronic address: [email protected].

PMID: 28482193
DOI: 10.1016/j.carres.2017.04.020

Abstract

A pyridyl triazole (pyta) modified sucrose ligand was prepared in a seven step synthesis using d-glucose as the protection group for d-fructose and starting from commercially available sucrose. After complexation with Ru(bpy)₂Cl₂ precursor, the sucrose-conjugated Ru complex of the general formula [Ru(bpy)₂(L)]Cl₂ was formed. Acidic cleavage of the d-glucose unit led to the first d-fructose conjugated metal complex viad-fructose C6 in literature. Additionally, pyta-modified d-fructose via C1 and the corresponding Ru complex were synthesized. All compounds were analyzed by R_f values, specific rotation, NMR, IR, UV/Vis and fluorescence spectroscopy, mass spectrometry and elemental analysis.

Keywords: Carbohydrates; Click chemistry; Metal complexes; Sucrose; d-fructose.

MeSH terms

2,2'-Dipyridyl / analogs & derivatives*
2,2'-Dipyridyl / chemistry
Alkynes / chemistry
Azides / chemistry
Biological Transport
Catalysis
Click Chemistry
Copper / chemistry
Fructose / chemistry*
Humans
Ligands
MCF-7 Cells
Organometallic Compounds / chemistry*
Sucrose / chemical synthesis*
Sucrose / chemistry*
Sucrose / pharmacology
Triazoles / chemistry

Substances

Alkynes
Azides
Ligands
Organometallic Compounds
Triazoles
bis(bipyridyl)ruthenium(II)
Fructose
2,2'-Dipyridyl
Sucrose
Copper