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

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)(2)Cl-2 precursor, the sucrose-conjugated Ru complex of the general formula...

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Published inCarbohydrate research Vol. 446; pp. 19 - 27
Main Authors Proehl, Michael, Moser, Pascal D., Czaplewska, Justyna A., Hoffmann, Patrick, Bus, Tanja, Traeger, Anja, Goerls, Helmar, Schubert, Ulrich S., Gottschaldt, Michael
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier 29.06.2017
Subjects
Biochemistry & Molecular Biology
Chemistry
Chemistry, Applied
Chemistry, Organic
Life Sciences & Biomedicine
Physical Sciences
Science & Technology
Carbohydrates
CELLS
AZIDES
ACID
Sucrose
D-fructose
CHEMISTRY
ISOMERS
Click chemistry
Metal complexes
COPOLYMERIZATION
CELLULAR UPTAKE
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Summary: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)(2)Cl-2 precursor, the sucrose-conjugated Ru complex of the general formula [Ru(bPY)(2)(L)]Cl-2 was formed. Acidic cleavage of the o-glucose unit led to the first o-fructose conjugated metal complex via o-fructose C6 in literature. Additionally, pyta-modified D-fructose via Cl 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. (C) 2017 Elsevier Ltd. All rights reserved.
ISSN:0008-6215
1873-426X
DOI:10.1016/j.carres.2017.04.020