Mechanism of racemisation of histidine derivatives in peptide synthesis.

  title={Mechanism of racemisation of histidine derivatives in peptide synthesis.},
  author={Joshua H Jones and W I Ramage and M J Witty},
  journal={International journal of peptide and protein research},
  volume={15 3},
Evidence is presented to show that the racemisation of N(alpha)-benzyloxycarbonyl-N(pi)-phenacyl-L-histidine which occurs on activation with dicyclohexylcarbodiimide in dimethylformamide takes place by action of the pi-nitrogen as an intramolecular base catalyst in the O-acylisourea adduct which is in reversible equilibrium with the reactants, rather than by formation of an optically labile heterocyclic intermediate. 

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