Synthesis of fluorinated maltose derivatives for monitoring protein interaction by ¹⁹F NMR

• Michaela Braitsch,
• Hanspeter Kählig,
• Georg Kontaxis,
• Michael Fischer,
• Toshinari Kawada,
• Robert Konrat and
• Walther Schmid

Beilstein J. Org. Chem. 2012, 8, 448–455, doi:10.3762/bjoc.8.51

• studies of protein–ligand interaction interfaces. Keywords: fluorination; 19F NMR; maltose-binding protein (MBP); maltose derivatives; protein interaction; Introduction In recent years, we have witnessed significant improvements in NMR spectroscopy, especially as a powerful tool for studying protein

• binding affinities of various fluorinated and nonfluorinated maltose derivatives to MBP in competitive titration experiments. The incorporation of fluorine in different positions into maltose allows fine tuning of the carbohydrate affinities to the maltose-binding protein. Results and Discussion Syntheses

• Deoxofluor [38] yielded the 6-F-maltose derivatives 18. Final deprotection with acetic acid [37][39] and sodium methoxide yielded compound 20. The synthesis of the galacto-type derivative 23 started from peracetylated benzylidene maltose 11 [37]. Deprotection [37] with acetic acid followed by microwave