Formation of a cyclic imide in aspartyl or asparaginyl glycyl peptides induced by heating in the dry state*
- 12 January 2009
- journal article
- research article
- Published by Wiley in International Journal of Peptide and Protein Research
- Vol. 29 (6), 728-733
- https://doi.org/10.1111/j.1399-3011.1987.tb02305.x
Abstract
A common product was identified by HPLC from the heating of .alpha. and .beta. isomers of aspartyl glycine in the dry state. Fast atom-bombardment (FAB) mass spectrometry and Fourier transform infrared photoacoustic spectroscopy (FTIR-PAS) showed tthat the product is a cyclic imide. Cyclic imide formation also was shown to occur with the tripeptides Gly-Asp-Gly and Gly-Asn-Gly. The cyclization of aspartyl peptides depends upon protonation of the .beta.-carboxyl group and can be promoted by acidification or by heating the NH4+ salt in the dry state.Keywords
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