Lactam

What is Lactam?

A lactam is a cyclic amide, which is derived from an amino alkanoic acid. The term is a portmanteau of the words acetone + amide.

Lactams form by the acid-catalysed rearrangement of oximes in the Beckmann rearrangement. Lactams form from cyclic ketones and hydrazoic acid in the Schmidt reaction. Lactams form from cyclisation of amino acids.

Table of Contents

• Synthesis of Lactam
• Structure of Lactam
• Types of Lactam
• Uses of Lactam
• Frequently Asked Questions – FAQs

Synthesis of Lactam

Aminolysis of various difunctional chemicals, such as amino esters, diesters, or diamines, can be used to make lactams or di-lactams. Lactams are formed when oximes undergo an acid-catalysed Beckmann rearrangement. 

Lactams are formed when linear acyl derivatives are attacked intramolecularly during the nucleophilic abstraction reaction. An iminium ion combines with a halonium ion generated in situ by reacting an alkene with iodine in iodolactonisation. Other lactams are also known, but they are not generated by the thermal elimination of water between COOH and NH₂ from the same molecule.

Types of Lactam

Lactams are cyclic amides that come in a variety of forms, including 

1. α-Lactam (3-atom rings)
2. β-Lactam (4-atom rings)
3. γ-Lactam (5-atom rings)
4. δ-Lactam (6-atom rings)
5. ε-Lactam (7-atom rings)

Lactam is a key component in medication development. 2-pyrrolidone derivatives include povidone, cotinine, ethosuximide, piracetam, and doxapram, among others. The molecular structure of 2-pyrrolidone. The dipole moment of the five-membered lactams, namely 2-pyrrolidone, has been calculated in several investigations.

Structure of Lactam

Uses of Lactam

• Antibiotic resistance is provided by beta-lactamase, which breaks the structure of antibiotics. A four-atom ring known as alpha-lactam is present in all of these antibiotics’ molecular structures.
• Antibiotics with alpha-lactams are used to prevent and cure bacterial infections caused by susceptible organisms.
• Through Mo-catalyzed desymmetrisation of easily available achiral polyene substrates, optically enriched N-fused bicyclic amides and small- and medium-ring unsaturated cyclic amines may be produced in up to 98 percent.
• The peptidoglycan layer of bacterial cell walls is inhibited by -lactam antibiotics, making them bactericidal. Because it is the outermost and fundamental component of the cell wall, the peptidoglycan layer is critical for cell wall structural integrity, especially in Gram-positive species.