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); maltosederivatives; 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 maltosederivatives 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-maltosederivatives 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
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Graphical Abstract
Figure 1:
Schematic diagram of the network of hydrogen bonds in the binding pocket of the complex between MBP...