7-AB

Chemical compound

Chemical structure of 7-AB

7-AB is a chemical compound that serves as an important intermediate in the synthesis of various cephalosporin antibiotics. It is a derivative of the beta-lactam class of antibiotics, which are characterized by their four-membered lactam ring. The full name of 7-AB is 7-aminocephalosporanic acid.

Chemical Structure

7-AB is structurally related to penicillins, sharing the beta-lactam ring that is crucial for its antibacterial activity. The core structure of 7-AB consists of a bicyclic system that includes a beta-lactam ring fused to a dihydrothiazine ring. This unique structure is responsible for its ability to inhibit bacterial cell wall synthesis.

Synthesis

The synthesis of 7-AB typically involves the fermentation of certain fungi or bacteria that produce cephalosporin C, which is then chemically modified to yield 7-AB. This process involves the removal of the side chain from cephalosporin C to produce the 7-amino group, which is a key functional group in the synthesis of various cephalosporin antibiotics.

Applications

7-AB is primarily used as a building block in the pharmaceutical industry for the production of cephalosporin antibiotics. These antibiotics are used to treat a wide range of bacterial infections, particularly those caused by Gram-positive and some Gram-negative bacteria. The modification of the 7-AB structure allows for the development of cephalosporins with different spectrums of activity and pharmacokinetic properties.

Mechanism of Action

The antibacterial activity of 7-AB-derived cephalosporins is due to their ability to bind to and inhibit penicillin-binding proteins (PBPs) in bacterial cell walls. This inhibition prevents the cross-linking of peptidoglycan chains, which is essential for bacterial cell wall integrity, ultimately leading to cell lysis and death.

Related Compounds

7-AB is closely related to other beta-lactam antibiotics, such as penicillins and carbapenems. These compounds share a similar mechanism of action but differ in their chemical structures and spectra of activity.

Related Pages

• Cephalosporin
• Beta-lactam antibiotic
• Penicillin
• Antibiotic resistance