Benzamidine
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Through Organic compound, Aryl group and Ligand
Structure
Benzamidine has one short C=NH bond and one longer C-NH2 bond, which are respectively 129 and 135 pm in length, respectively.
The triangular diamine group gives it a distinctive shape which shows up in difference density maps.
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Applications
Benzamidine is a reversible competitive inhibitor of trypsin, trypsin-like enzymes, and serine proteases.
It is often used as a ligand in protein crystallography to prevent proteases from degrading a protein of interest. The benzamidine moiety is also found in some pharmaceuticals, such as dabigatran.
Condensation with various haloketones provides a synthetic route to 2,4-disubstituted imidazoles.