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Benzamidine

Benzamidine is an organic compound with the formula C6H5C(NH)NH2. It is the simplest aryl amidine. The compound is a white solid that is slightly soluble in water. It is usually handled as the hydrochloride salt, a white, water-soluble solid.

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.

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. :[[File:Disubstituted-imidazole-synthesis OrgSyn.png|400px]]

References

References

  1. Armarego, W. L. F.. (2003). "Purification of Laboratory Chemicals". Butterworth-Heinemann.
  2. (2005). "Preparation of 2,4-Disubstituted Imidazoles: 4-(4-Methoxyphenyl)-2-Phenyl-1''H''-Imidazole". Organic Syntheses.
  3. (1996). "Benzamidine". Acta Crystallographica Section C Crystal Structure Communications.
  4. Tanizawa, Kazutaka. (1971-05-01). "Proteolytic Enzymes. VI. Aromatic Amidines as Competitive Inhibitors of Trypsin". The Journal of Biochemistry.
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phenyl-compounds amidines
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