Mechanisms of Preferential and Selective Cleavages

At this point it becomes useful to make a clear distinction between preferential (competitive or hydrolytic) and selective (noncompetitive, non-hydrolytic) cleavages, which are governed by different principles and mechanisms. 

Mechanisms of Preferential Cleavage through Neighboring Hydroxyl Groups 

Survey of Principles and Reactions Employed in the Preferential or Selective Cleavage of Peptide Bonds 

Amino acid Functional group Cleaving agent Type of cleavage Yield Reference 

Serine, threonine l8-Hydroxyl Strong acids (H2SO4, HjFj, etc.) A — 0 Acyl shift 60% (impractical for many proteins) Elliott, 1953 Narita, 1959 Fasman, 1960 Iwai, 1960 

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