Exploitation of Dimeric Cyclic Cysteine as Helix Inducer in Ultra‐Short Peptides for Cu (II)‐Catalyzed Asymmetric Michael Addition on Chalcones

Abstract: A dimeric cyclic cysteine analogue, i.e. (1R,1′R,2R,2′R)‐2,2′‐disulfanediylbis (aminocyclohexane‐1‐carboxylic acid), was used as a constrained unnatural amino acid and as a folding inducer in ultra‐short Leu‐Val‐containing peptide. Our results showed that both free dimer amino acid L1 and its peptide derivative L2 are able to chelate Cu (II). The obtained complexes resulted to be catalytically active in Michael addition reaction of nitromethane on different types of chalcones. L1‐Cu (II) was shown more reactive in terms of conversion, while, in neat conditions, L2‐Cu (II) allows to obtain an interesting 60 % e.e. on pyridine chalcone.

Object Details

• Location: Deutsche Nationalbibliothek Frankfurt am Main
• Extent: Online-Ressource
• Language: Englisch

References and Relationships

• Bibliographic citation: Exploitation of Dimeric Cyclic Cysteine as Helix Inducer in Ultra‐Short Peptides for Cu (II)‐Catalyzed Asymmetric Michael Addition on Chalcones ; day:04 ; month:05 ; year:2023 ; extent:9 ; European journal of organic chemistry ; (04.05.2023) (gesamt 9)

Contributors, Places and Time

• Creator: Facchetti, Giorgio ; Vitoria, Jaime Gracia ; Moraschi, Martina ; Bucci, Raffaella ; Abel, Anne Catherine ; Pieraccini, Stefano ; Pellegrino, Sara ; Rimoldi, Isabella

Further information

• DOI: 10.1002/ejoc.202300240
• URN: urn:nbn:de:101:1-2023050515060229293405
• Rights: Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
• Last update: 14.08.2025, 11:00 AM CEST