Prevention of diketopiperazine formation in peptide synthesis by a simultaneous deprotection–coupling procedure: entrapment of reactive nucleophilic species by in situ acylation

Authors:
  • RSRichard E. Shute
    Richard E. Shute
  • DRDaniel H. Rich
    Daniel H. Rich
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Abstract
Hydrogenolysis of Z-amino acid-D-Pro-OMe dipeptides in the presence of acetic acid results, almost quantitavely, in the formation of diketopiperazines, whereas in the presence of Boc- or 2-(trimethylsilyl)ethoxycarbonyl protected amino acid pentafluorophenyl or N-hydroxysuccinimidyl active esters, protected tripeptides are formed; a simultaneous deprotection/acylation methodology with potential utility for peptide synthesis thus results.