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Synthesis of rigid tryptophan mimetics by the diastereoselective Pictet–Spengler reaction of β 3 ‐ homo ‐tryptophan derivatives with chiral α ‐amino aldehydes
Author(s) -
Slupska Marta,
PulkaZiach Karolina,
Deluga Edyta,
Sosnowski Piotr,
Wilenska Beata,
Kozminski Wiktor,
Misicka Aleksandra
Publication year - 2015
Publication title -
journal of peptide science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.475
H-Index - 66
eISSN - 1099-1387
pISSN - 1075-2617
DOI - 10.1002/psc.2832
Subject(s) - stereocenter , chemistry , diastereomer , aldehyde , tryptophan , pictet–spengler reaction , amino acid , stereochemistry , condensation reaction , carbon 13 nmr , peptide , condensation , enantioselective synthesis , organic chemistry , catalysis , biochemistry , physics , thermodynamics
The Pictet–Spengler (PS) cyclizations of β 3 ‐ h Trp derivatives as arylethylamine substrates were performed with L‐ α ‐amino and D‐ α ‐amino aldehydes as carbonyl components. During the PS reaction, a new stereogenic center was created, and the mixture of cis/trans 1,3‐disubstituted 1,2,3,4‐tetrahydro‐ β ‐carbolines was obtained. The ratio of cis/trans diastereomers depends on the stereogenic centre of used amino aldehyde and the size of substituents. It was confirmed by 1H and 2D NMR (ROESY) spectra. The conformations of cyclic products were studied by 2D NMR ROESY spectra. Products of the PS condensation after removal of protecting group(s) can be incorporated into a peptide chain as tryptophan mimetics with the possibility of the β ‐turn induction. Copyright © 2015 European Peptide Society and John Wiley & Sons, Ltd.