Question 4: In analogy to transesterification, transamidation is a reaction where one amide is converted into...

Transcribed Image Text:

Question 4: In analogy to transesterification, transamidation is a reaction where one amide is converted into another in the presence of an amine nucleophile. Transamidation is typically a very slow and ineffective process. An exception is the reaction of penicillin with amidase enzymes, which are involved in the biosynthesis of bacterial cell walls and are essential for survival of bacteria. Penicillin reacts with an amine group in the enzyme's active site to form a covalent amide adduct and inactivates the enzyme. a) Using the provided scheme, draw the product of the reaction between penicillin and amidase. -NH Bacterial Amidase enzyme Ph S CH3 Y"CH3 COH penicilin Transamidation reaction -NH Amidase covalently-inhibited by penicilin b) Explain the increased reactivity of penicillin toward transamidation. Question 4: In analogy to transesterification, transamidation is a reaction where one amide is converted into another in the presence of an amine nucleophile. Transamidation is typically a very slow and ineffective process. An exception is the reaction of penicillin with amidase enzymes, which are involved in the biosynthesis of bacterial cell walls and are essential for survival of bacteria. Penicillin reacts with an amine group in the enzyme's active site to form a covalent amide adduct and inactivates the enzyme. a) Using the provided scheme, draw the product of the reaction between penicillin and amidase. -NH Bacterial Amidase enzyme Ph S CH3 Y"CH3 COH penicilin Transamidation reaction -NH Amidase covalently-inhibited by penicilin b) Explain the increased reactivity of penicillin toward transamidation.

Answer rating: 100% (QA)

The image contains a question related to the chemical reaction between penicillin and a bacterial amidase enzyme through a process called transamidati... View the full answer