Peptide Bond Formation: Activating Carboxylic Acids to Form Amides (DCC/HATU Logic)

Learn peptide coupling: carboxyl activation, amine attack, and why coupling reagents prevent unfavorable direct condensation. Includes common side reactions and fixes.

  • Reaction: Amino acid + amino acid → dipeptide
  • What it does: Forms amide (peptide) bond efficiently
  • Typical reagents: DCC (often with HOBt) or modern reagents like HATU/EDC
  • Key intermediate: Activated ester / O-acylurea (with DCC)
  • Driving force: Activation makes acyl substitution feasible; byproduct urea formation
  • Exam type: Synthesis planning
  • Exam type: Acyl substitution

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