BROMAMPHENICOL

• CAT Number: M086892
• CAS Number: 16803-75-1
• Molecular Formula: C11H12Br2N2O5
• Molecular Weight: 412.034
• Purity: 98%
• Storage: -20°C
• Analysis method: HPLC
• IUPAC Name: 2,2-dibromo-N-[(1R,2R)-1,3-dihydroxy-1-(4-nitrophenyl)propan-2-yl]acetamide
• InChI: InChI=1S/C11H12Br2N2O5/c12-10(13)11(18)14-8(5-16)9(17)6-1-3-7(4-2-6)15(19)20/h1-4,8-10,16-17H,5H2,(H,14,18)/t8-,9-/m1/s1
• InChIKey: UWOHGNMWBGIRAQ-RKDXNWHRSA-N
• SMILES: C1=CC(=CC=C1C(C(CO)NC(=O)C(Br)Br)O)[N+](=O)[O-]

Bromamphenicol(cas 16803-75-1) is a semi-synthetic chloramphenicol analogue first reported in 1950, in which the dichloroacetamide is
replaced with dibromoacetamide. Bromamphenicol possesses weak antibiotic activity. Comparative crystallography with
chloramphenicol helped defined the SARs of the acetamide binding region on the ribosome. More recently, this relationship
was used to demonstrate that chloramphenicol binding to DraE virulence factors in Gram negative bacteria was independent of
chloramphenicol binding site on the ribosome.

Reference

X-Ray analysis of some antibiotic substances. Dunitz J.D. & Leonard J.E. J. Am. Chem. Soc. 1950, 72, 4276.

The crystal structure of chloramphenicol and bromamphenicol. Dunitz J.D. J. Am. Chem. Soc. 1952, 74, 995.

A structural study of the interaction between the Dr haemagglutinin DraE and derivatives of chloramphenicol. Pettigrew D.M. et al. Acta Cryst. Set. D 2009, 65, 513.