title: Peptides and peptidoaldehydes as substrates for the Pictet-Spengler reaction.
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.
authors.affiliation: Faculty of Chemistry, University of Warsaw, Pasteura 1, 02-093, Warsaw, Poland. karola@chem.uw.edu.pl
authors.forename: Karolina
authors.initials: K
authors.lastname: Pulka
authors.forename: Marta
authors.initials: M
authors.lastname: Slupska
authors.forename: Anna
authors.initials: A
authors.lastname: Puszko
authors.forename: Maria
authors.initials: M
authors.lastname: Misiak
authors.forename: Marcin
authors.initials: M
authors.lastname: Wilczek
authors.forename: Wiktor
authors.initials: W
authors.lastname: Kozminski
authors.forename: Aleksandra
authors.initials: A
authors.lastname: Misicka
mesh_terms: D000447:Aldehydes / Q000138:chemical synthesis* / Q000737:chemistry*; D003500:Cyclization; D015394:Molecular Structure; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D010455:Peptides