nounIntermediate
Definition
Acid-labile N-terminal protecting group used in the original Merrifield solid-phase peptide synthesis method; largely replaced by the base-labile Fmoc group in modern SPPS.

Detailed Explanation

The first protecting group strategy for SPPS, developed alongside Merrifield's Nobel Prize-winning method. Boc is removed with trifluoroacetic acid (TFA) at each deprotection step, and the final global deprotection uses hydrofluoric acid (HF) — a hazardous reagent that drove the field to adopt the milder Fmoc chemistry. Boc SPPS remains useful for certain aggregation-prone sequences and specialized applications.

Key Facts

  • The first protecting group strategy for SPPS, developed alongside Merrifield's Nobel Prize-winning method
  • Boc is removed with trifluoroacetic acid (TFA) at each deprotection step, and the final global deprotection uses hydrofluoric acid (HF) — a hazardous reagent that drove the field to adopt the milder Fmoc chemistry
  • Boc SPPS remains useful for certain aggregation-prone sequences and specialized applications
Related Terms Fmoc SPPS Coupling Reagent

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