Mets7 is a methionine‐rich motif present in hCtr‐1 transporter that is involved in copper cellular trafficking. Its ability to bind Cu(I) was recently exploited to develop metallopeptide catalysts for Henry condensation. Here, the catalytic activity of Mets7‐Cu(I) complex in Michael addition reactions has been evaluated. Furthermore, His7 peptide, in which Met residues have been substituted with His ones, was also prepared. This substitution allowed His7 to coordinate Cu (II), with the obtainment of a stable turn conformation as evicted by CD experiments. His7‐Cu (II) proved also to be a better catalyst than Mets7‐Cu(I) in the addition reaction. In particular, when the substrate was the (E)‐1‐phenyl‐3‐(pyridin‐2‐yl)prop‐2‐en‐1‐one, a conversion of 71% and a significative 58% of e.e. was observed.

Exploring the copper binding ability of Mets7 hCtr‐1 protein domain and His7 derivative: An insight in Michael addition catalysis / I. Rimoldi, R. Bucci, L. Feni, L. Santagostini, G. Facchetti, S. Pellegrino. - In: JOURNAL OF PEPTIDE SCIENCE. - ISSN 1075-2617. - (2020). [Epub ahead of print] [10.1002/psc.3289]

Exploring the copper binding ability of Mets7 hCtr‐1 protein domain and His7 derivative: An insight in Michael addition catalysis

Isabella Rimoldi;Raffaella Bucci;Lucia Feni;Laura Santagostini;Giorgio Facchetti;Sara Pellegrino
2020

Abstract

Mets7 is a methionine‐rich motif present in hCtr‐1 transporter that is involved in copper cellular trafficking. Its ability to bind Cu(I) was recently exploited to develop metallopeptide catalysts for Henry condensation. Here, the catalytic activity of Mets7‐Cu(I) complex in Michael addition reactions has been evaluated. Furthermore, His7 peptide, in which Met residues have been substituted with His ones, was also prepared. This substitution allowed His7 to coordinate Cu (II), with the obtainment of a stable turn conformation as evicted by CD experiments. His7‐Cu (II) proved also to be a better catalyst than Mets7‐Cu(I) in the addition reaction. In particular, when the substrate was the (E)‐1‐phenyl‐3‐(pyridin‐2‐yl)prop‐2‐en‐1‐one, a conversion of 71% and a significative 58% of e.e. was observed.
Michael reaction; chalcone; copper; hybrid catalyst; metallopeptide;
Settore CHIM/06 - Chimica Organica
Settore CHIM/03 - Chimica Generale e Inorganica
22-ott-2020
JOURNAL OF PEPTIDE SCIENCE
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/2434/777908
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