Prevention of diketopiperazine formation in peptide synthesis by a simultaneous deprotection–coupling procedure: entrapment of reactive nucleophilic species by in situ acylation
- 1 January 1987
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Chemical Communications
- No. 15,p. 1155-1156
- https://doi.org/10.1039/c39870001155
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.Keywords
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