To determine the nucleophilic site on serine that is most likely to be acylated by penicillin, we must consider the nature of the functional groups present in serine and the mechanism of action of penicillin.

1. **Understanding the Functional Groups**: Serine has a side chain containing a hydroxyl group (-OH) as well as an amino group (-NH2) and a carboxyl group (-COOH) in its main structure.

2. **Nucleophilic Sites**: The hydroxyl (-OH) group in the side chain acts as a nucleophile, which means it can donate a pair of electrons to form a new bond.

3. **Penicillin's Mechanism**: Penicillin acts by acylating the active site serine in bacterial transpeptidases, which is often facilitated by the electrophilic carbonyl carbon of the penicillin molecule reacting with the nucleophilic hydroxyl of serine.

4. **Most Likely Site for Acylation**: Given the properties of serine and the mechanism of penicillin, the side chain -OH in serine is the most reactive nucleophilic site that is likely to undergo acylation.

### Final Answer
A. Side chain -OH

Question

To determine the nucleophilic site on serine that is most likely to be acylated by penicillin, we must consider the nature of the functional groups present in serine and the mechanism of action of penicillin.

1. **Understanding the Functional Groups**: Serine has a side chain containing a hydroxyl group (-OH) as well as an amino group (-NH2) and a carboxyl group (-COOH) in its main structure.

2. **Nucleophilic Sites**: The hydroxyl (-OH) group in the side chain acts as a nucleophile, which means it can donate a pair of electrons to form a new bond.

3. **Penicillin's Mechanism**: Penicillin acts by acylating the active site serine in bacterial transpeptidases, which is often facilitated by the electrophilic carbonyl carbon of the penicillin molecule reacting with the nucleophilic hydroxyl of serine.

4. **Most Likely Site for Acylation**: Given the properties of serine and the mechanism of penicillin, the side chain -OH in serine is the most reactive nucleophilic site that is likely to undergo acylation.

### Final Answer
A. Side chain -OH

Knowee AI · Accepted Answer

To determine the nucleophilic site on serine that is most likely to be acylated by penicillin, we must consider the nature of the functional groups present in serine and the mechanism of action of penicillin.

1. **Understanding the Functional Groups**: Serine has a side chain containing a hydroxyl group (-OH) as well as an amino group (-NH2) and a carboxyl group (-COOH) in its main structure.

2. **Nucleophilic Sites**: The hydroxyl (-OH) group in the side chain acts as a nucleophile, which means it can donate a pair of electrons to form a new bond.

3. **Penicillin's Mechanism**: Penicillin acts by acylating the active site serine in bacterial transpeptidases, which is often facilitated by the electrophilic carbonyl carbon of the penicillin molecule reacting with the nucleophilic hydroxyl of serine.

4. **Most Likely Site for Acylation**: Given the properties of serine and the mechanism of penicillin, the side chain -OH in serine is the most reactive nucleophilic site that is likely to undergo acylation.

### Final Answer
A. Side chain -OH

At which nucleophilic site is serine MOST likely to be acylated by penicillin? A.Side chain -OHB.Carbonyl carbonC.CarboxylateD.ɑ-Carbon

Question

At which nucleophilic site is serine MOST likely to be acylated by penicillin?

Solution

Final Answer

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