Synthesis of rigid tryptophan mimetics by the diastereoselective Pictet-Spengler reaction of β³-homo-tryptophan derivatives with chiral α-amino aldehydes

Journal of Peptide Science : an Official Publication of the European Peptide Society
Marta SlupskaAleksandra Misicka

Abstract

The Pictet-Spengler (PS) cyclizations of β(3)-hTrp 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.

References

Jan 1, 1985·Advances in Protein Chemistry·G D RoseJ A Smith
Nov 17, 2001·Chemical Reviews·R P ChengW F DeGrado
May 13, 2004·Chemical Reviews·Jacques RoyerLaurent Micouin
Jun 15, 2005·Angewandte Chemie·Hang Yin, Andrew D Hamilton
Oct 20, 2005·Biopolymers·Dieter SeebachAlice Glättli
Jan 26, 2006·Journal of the American Chemical Society·Jayasree SeayadBenjamin List
Feb 16, 2008·Biopolymers·Anna Marie C Marcelino, Lila M Gierasch
Jun 17, 2009·Molecular Diversity·Karolina PulkaDirk Tourwé
Aug 11, 2011·Angewandte Chemie·Joachim StöckigtHerbert Waldmann
Aug 23, 2012·Peptides·Alice B Nongonierma, Richard J Fitzgerald
Oct 18, 2012·Organic & Biomolecular Chemistry·Giordano LesmaAlessandra Silvani
Nov 3, 2012·European Journal of Medicinal Chemistry·Nermin S AhmedAshraf H Abadi
Dec 5, 2012·Bioorganic & Medicinal Chemistry Letters·Giorgio OrtarVincenzo Di Marzo
May 29, 2013·Journal of Peptide Science : an Official Publication of the European Peptide Society·Karolina PulkaAleksandra Misicka

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Citations

Jan 23, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Andrea CalcaterraFrancesca Ghirga

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