Reactions of C‐terminal ω‐amino acid residues in liquid hydrogen fluoride
- 1 July 1993
- journal article
- Published by Wiley in International Journal of Peptide and Protein Research
- Vol. 42 (1) , 10-13
- https://doi.org/10.1111/j.1399-3011.1993.tb00342.x
Abstract
The benzyl-ester bond linking the C-terminal δ-aminovaleric acid residue of a peptide to a polymeric support was cleaved with liquid hydrogen fluoride in the presence of anisole, added as scavenger. Instead of the expected peptide with a free carboxyl group at the C-terminus, a peptide terminating in a ketone derivative was obtained. The unusual extent of this known side-reaction was attributed to the effect of the distance between the amino group and the carboxyl group in the C-terminal residue. The results of model experiments corroborated this view.Keywords
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