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Peptides and peptidoaldehydes as substrates for the Pictet-Spengler reaction.

Authors :
Pulka, Karolina
Slupska, Marta
Puszko, Anna
Misiak, Maria
Wilczek, Marcin
Kozminski, Wiktor
Misicka, Aleksandra
Source :
Journal of Peptide Science; Jul2013, Vol. 19 Issue 7, p433-440, 8p
Publication Year :
2013

Abstract

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. [ABSTRACT FROM AUTHOR]

Details

Language :
English
ISSN :
10752617
Volume :
19
Issue :
7
Database :
Complementary Index
Journal :
Journal of Peptide Science
Publication Type :
Academic Journal
Accession number :
88058917
Full Text :
https://doi.org/10.1002/psc.2516