Racemization

  1. Definition of Racemization:

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

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

Examples:           

  1. Example Reaction (Racemization of Amino Acids):
    •  L-AminoAcid —[pH, temperature]→ D-AminoAcid
  2. Thalidomide: One enantiomer is therapeutic, while the other is teratogenic.
  3. Epinephrine: Converts to inactive isomers at higher pH.

Prevention Strategies of Racemization:

  • Optimize pH and temperature during storage.
  • Stabilize formulations using buffers.
  • Choose enantiomerically pure drugs if racemization poses a risk.

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