Bromamphenicol
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| Category | Antibiotics |
| Catalog number | BBF-04216 |
| CAS | 16803-75-1 |
| Molecular Weight | 412.03 |
| Molecular Formula | C11H12Br2N2O5 |
| Purity | >99% by HPLC |
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Description
It is produced by the strain of Streptomyces sp. 3022 in the presence of potassium bromide. It is a semisynthetic chloramphenicol analogue with dibromoacetamide instead of dichloroacetamide. It has weak antibacterial activity.
Specification
| Related CAS | 17371-30-1 |
| Synonyms | N-[(1R,2R)-1-(Hydroxymethyl)-2-hydroxy-2-(4-nitrophenyl)ethyl]-2,2-dibromoacetamide; 2,2-Dibromo-N-[β-hydroxy-α-(hydroxymethyl)-p-nitrophenethyl]-acetamide; Bromomycin |
| Storage | Store at -20°C |
| IUPAC Name | 2,2-dibromo-N-[(1R,2R)-1,3-dihydroxy-1-(4-nitrophenyl)propan-2-yl]acetamide |
| Canonical SMILES | C1=CC(=CC=C1C(C(CO)NC(=O)C(Br)Br)O)[N+](=O)[O-] |
| 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 |
| InChI Key | UWOHGNMWBGIRAQ-RKDXNWHRSA-N |
| Source | Semi-synthetic |
Properties
| Appearance | White Solid |
| Antibiotic Activity Spectrum | Bacteria |
| Boiling Point | 664.4±55.0°C at 760 mmHg |
| Melting Point | 152-153°C |
| Density | 1.9±0.1 g/cm3 |
| Solubility | Soluble in Ethanol, Methanol, DMF, DMSO; Poorly soluble in Water |
Reference Reading
1. A structural study of the interaction between the Dr haemagglutinin DraE and derivatives of chloramphenicol
Pietro Roversi, Susan M Lea, Angela J Russell, David M Pettigrew, Stephen G Davies Acta Crystallogr D Biol Crystallogr . 2009 Jun;65(Pt 6):513-22. doi: 10.1107/S0907444909005113.
Dr adhesins are expressed on the surface of uropathogenic and diffusely adherent strains of Escherichia coli. The major adhesin subunit (DraE/AfaE) of these organelles mediates attachment of the bacterium to the surface of the host cell and possibly intracellular invasion through its recognition of the complement regulator decay-accelerating factor (DAF) and/or members of the carcinoembryonic antigen (CEA) family. The adhesin subunit of the Dr haemagglutinin, a Dr-family member, additionally binds type IV collagen and is inhibited in all its receptor interactions by the antibiotic chloramphenicol (CLM). In this study, previous structural work is built upon by reporting the X-ray structures of DraE bound to two chloramphenicol derivatives: chloramphenicol succinate (CLS) and bromamphenicol (BRM). The CLS structure demonstrates that acylation of the 3-hydroxyl group of CLM with succinyl does not significantly perturb the mode of binding, while the BRM structure implies that the binding pocket is able to accommodate bulkier substituents on the N-acyl group. It is concluded that modifications of the 3-hydroxyl group would generate a potent Dr haemagglutinin inhibitor that would not cause the toxic side effects that are associated with the normal bacteriostatic activity of CLM.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
