What is the chemical structure of Chloramphenicol?

Chloramphenicol is a well - known antibiotic with a rich history in the field of medicine. As a key supplier of Chloramphenicol, understanding its chemical structure is fundamental not only for scientific enthusiasts but also for those involved in the pharmaceutical industry. In this blog, we will delve deep into the chemical structure of Chloramphenicol, exploring its components, properties, and the implications of its structure on its biological activity.

Chemical Formula and Molecular Weight

The chemical formula of Chloramphenicol is (C_{11}H_{12}Cl_{2}N_{2}O_{5}). This formula indicates that a single molecule of Chloramphenicol consists of 11 carbon atoms, 12 hydrogen atoms, 2 chlorine atoms, 2 nitrogen atoms, and 5 oxygen atoms. The molecular weight of Chloramphenicol is approximately 323.13 g/mol. This relatively large molecular weight is due to the combination of various atoms and functional groups within the molecule, which play crucial roles in its biological function.

Structural Features

Functional Groups

• Nitrobenzene Group: At one end of the Chloramphenicol molecule, there is a nitrobenzene group ((NO_{2}-C_{6}H_{4}-)). The nitro group ((NO_{2})) is an electron - withdrawing group, which affects the electronic properties of the benzene ring. It can influence the reactivity of the molecule and also plays a role in the interaction of Chloramphenicol with its biological targets. The benzene ring provides a stable aromatic structure, which is important for the overall shape and hydrophobicity of the molecule.
• Dichloroacetyl Group: Another significant functional group is the dichloroacetyl group ((Cl_{2}CH - CO -)). The two chlorine atoms in this group increase the electronegativity of the carbonyl carbon atom, making it more reactive towards nucleophilic attack. This group is also involved in the binding of Chloramphenicol to the ribosome, which is its main target in bacteria.
• Amino Alcohol Group: The central part of the Chloramphenicol molecule contains an amino alcohol group ((-NH - CH(OH)-CH_{2}-OH)). The amino group ((NH_{2})) can act as a base and form hydrogen bonds with other molecules. The hydroxyl groups ((OH)) contribute to the solubility of Chloramphenicol in water and also participate in hydrogen - bonding interactions with biological macromolecules.

Stereochemistry

Chloramphenicol has two chiral centers, which means it can exist in four possible stereoisomers. However, only the (D - (-)-threo) isomer has significant antibacterial activity. The specific configuration of the chiral centers in the active isomer is crucial for its binding to the bacterial ribosome. The correct stereochemistry allows Chloramphenicol to fit precisely into the binding site on the ribosome, inhibiting protein synthesis in bacteria.

Three - Dimensional Structure

The three - dimensional structure of Chloramphenicol is important for its biological activity. The molecule has a relatively compact structure, with the various functional groups arranged in a specific spatial orientation. The nitrobenzene group and the dichloroacetyl group are on opposite sides of the central amino alcohol chain. This arrangement allows Chloramphenicol to interact with the ribosome in a specific way. The ribosome has a binding pocket that is complementary in shape and charge to the Chloramphenicol molecule. When Chloramphenicol binds to the ribosome, it prevents the formation of peptide bonds between amino acids, thus inhibiting protein synthesis in bacteria.

Implications of the Chemical Structure on Biological Activity

The chemical structure of Chloramphenicol is directly related to its antibacterial activity. The specific functional groups and their spatial arrangement allow it to target the bacterial ribosome effectively. The nitrobenzene group and the dichloroacetyl group contribute to the hydrophobicity of the molecule, which helps it to penetrate the bacterial cell membrane. Once inside the cell, the amino alcohol group and other functional groups interact with the ribosome through hydrogen bonding, van der Waals forces, and electrostatic interactions.

The binding of Chloramphenicol to the ribosome is a reversible process. The specific chemical structure of Chloramphenicol allows it to compete with aminoacyl - tRNA for the binding site on the ribosome. By binding to the ribosome, Chloramphenicol prevents the elongation of the polypeptide chain, leading to the inhibition of protein synthesis and ultimately the death of the bacteria.

Related Compounds and Their Structures

In the pharmaceutical industry, there are often related compounds that share some structural features with Chloramphenicol. For example, (R)-1-[3,5-Bis(trifluoromethyl)phenyl]ethanol CAS#127852 - 28 - 2 is an intermediate compound. Although it has a different overall structure from Chloramphenicol, it also contains functional groups such as the phenyl ring and hydroxyl group. The trifluoromethyl groups in this compound increase its lipophilicity, which can affect its solubility and reactivity, similar to how the functional groups in Chloramphenicol influence its properties.

H - GLU - ALA - OH (Dipeptiven) CAS# 21064 - 18 - 6 is a dipeptide. While it has a completely different structure from Chloramphenicol, it also contains amino acid residues and functional groups such as amino and carboxyl groups. These functional groups are involved in various biological processes, similar to how the functional groups in Chloramphenicol are involved in its antibacterial activity.

Pyrroloquinoline Quinone (PQQ) CAS#72909 - 34 - 3 is a quinone compound. It has a heterocyclic structure with quinone functional groups. The quinone groups are involved in redox reactions, which are important for its biological functions, just as the functional groups in Chloramphenicol are involved in its interaction with the ribosome.

Importance of Understanding the Chemical Structure

As a Chloramphenicol supplier, understanding the chemical structure of Chloramphenicol is of utmost importance. It allows us to ensure the quality and purity of our products. By knowing the specific chemical structure, we can develop accurate methods for synthesis, purification, and analysis of Chloramphenicol. We can also optimize the production process to improve the yield and quality of the final product.

Moreover, understanding the chemical structure helps us to communicate effectively with our customers. We can provide them with detailed information about the properties and applications of Chloramphenicol. For example, we can explain how the chemical structure affects its solubility, stability, and antibacterial activity. This knowledge can also be used to develop new formulations of Chloramphenicol that are more effective and have fewer side effects.

Conclusion

In conclusion, the chemical structure of Chloramphenicol is a complex and fascinating subject. Its unique combination of functional groups, stereochemistry, and three - dimensional structure is responsible for its antibacterial activity. As a Chloramphenicol supplier, we are committed to providing high - quality products based on our in - depth understanding of its chemical structure. If you are interested in purchasing Chloramphenicol or have any questions about its properties and applications, please feel free to contact us for further discussion and negotiation.

References

1. "The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals", Merck & Co., Inc.
2. "Antibiotics: Actions, Origins, Resistance", Richard J. Roberts, et al.
3. "Principles of Medicinal Chemistry", Foye, W. O., et al.