Question

Tetracycline undergoes epimerization at C4 between pH 4-8 to give:

• A. Isotetracycline
• B. Doxycycline
• C. Epitetracycline
• D. Nortetracycline

Hint:

- Epimerization is a process where a molecule converts to its stereoisomer, affecting its pharmacological properties. 
- Tetracycline undergoes epimerization at the C4 position between pH 4-8, producing Nortetracycline.

Answer 1

The Correct Option is D

Tetracycline is an antibiotic that can undergo epimerization at the C4 position when exposed to pH levels between 4 and 8. This process involves a structural change at the C4 position, resulting in the formation of Nortetracycline, which is a stereoisomer of tetracycline. 
- Nortetracycline is formed when tetracycline epimerizes at the C4 position, a process that affects the drug's stereochemistry and can alter its pharmacological properties. 
- This epimerization typically occurs in the pH range of 4-8, where the molecule's geometry at the C4 position becomes unstable, leading to the formation of Nortetracycline. 

Why Other Options Are Incorrect: - (A) Isotetracycline: This is a different tetracycline derivative, but it is not formed by epimerization at C4. 
- (B) Doxycycline: Doxycycline is a derivative of tetracycline, but it does not result from epimerization at C4. 
- (C) Epitetracycline: While epimerization at the C4 position can result in different forms of tetracycline, Epitetracycline is not the primary product of this reaction. 

Thus, the correct epimerization product of tetracycline at pH 4-8 is Nortetracycline.