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Racemization

Definition:

  • Racemization is the interconversion of enantiomers (optical isomers) that can lead to changes in biological activity.

Mechanism:

  • A chiral molecule can transform into its mirror-image isomer under certain conditions (pH, temperature, etc.).

Examples:

  • Example Reaction (Racemization of Amino Acids):

Racemization
  • Thalidomide: One enantiomer is therapeutic, while the other is teratogenic.

  • Epinephrine: Converts to inactive isomers at higher pH.

Prevention Strategies:

  • Optimize pH and temperature during storage.

  • Stabilize formulations using buffers.

  • Choose enantiomerically pure drugs if racemization poses a risk.


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