Peptides and peptidoaldehydes as substrates for the Pictet–Spengler reaction
Article first published online: 28 MAY 2013
Copyright © 2013 European Peptide Society and John Wiley & Sons, Ltd.
Journal of Peptide Science
Volume 19, Issue 7, pages 433–440, July 2013
How to Cite
Pulka, K., Slupska, M., Puszko, A., Misiak, M., Wilczek, M., Kozminski, W. and Misicka, A. (2013), Peptides and peptidoaldehydes as substrates for the Pictet–Spengler reaction. J. Peptide Sci., 19: 433–440. doi: 10.1002/psc.2516
- Issue published online: 10 JUN 2013
- Article first published online: 28 MAY 2013
- Manuscript Accepted: 15 APR 2013
- Manuscript Revised: 10 APR 2013
- Manuscript Received: 4 FEB 2013
- Pictet–Spengler reaction;
- amino aldehydes;
- chemical ligation;
The Pictet–Spengler (PS) reaction was performed with various types of substrates: H-Trp-OMe and dipeptides with N-terminal Trp as arylethylamine components and Z-protected amino aldehydes and peptidoaldehydes as carbonyl components. We found that the C-terminal part of Trp derivatives did not have any influence on the stereoselectivity of the reaction and the results are the same for simple esters of Trp and dipeptides.
On the contrary, the selectivity of the PS reaction with peptidoaldehydes with L configuration of the C-terminus residue is totally different from that obtained with simple L-amino aldehydes. It allows us to obtain cis stereoisomers, which cannot be isolated from the reaction with amino aldehydes. But the utility of the peptidoaldehydes as substrates for the PS reaction is reduced by the side formation of enamides which decrease the yield of cyclization. Copyright © 2013 European Peptide Society and John Wiley & Sons, Ltd.