New copper(II)/cyclic tetrapeptide system that easily oxidizes to copper(III) under atmospheric oxygen

Alessandro Pratesi; Piero Zanello; Gianluca Giorgi; Luigi Messori; Franco Laschi; Angela Casini; Maddalena Corsini; Chiara Gabbiani; Marco Orfei; Claudia Rosani; Mauro Ginanneschi

doi:10.1021/ic701411y

New copper(II)/cyclic tetrapeptide system that easily oxidizes to copper(III) under atmospheric oxygen

Alessandro Pratesi, Piero Zanello, Gianluca Giorgi, Luigi Messori, Franco Laschi, Angela Casini, Maddalena Corsini, Chiara Gabbiani, Marco Orfei, Claudia Rosani, Mauro Ginanneschi

Research output: Contribution to journal › Article › peer-review

26 Scopus citations

Abstract

A 13-membered ring cyclic tetrapeptide was synthesized by the solid-phase peptide synthesis method, and its copper(II) coordination properties were analyzed by optical spectroscopy, mass spectrometry, and electrochemistry. All collected data strongly support the presence, at alkaline pH, of a stable peptide/copper-(III) complex that is formed in solution by atmospheric dioxygen oxidation. On the basis of previous studies on cyclic peptide/copper systems, we suggest that the copper(III) ion is at the center of the ligand's cavity being coordinated to four deprotonated amide nitrogen atoms. This donor set would greatly lower the redox potential for the Cu^III/Cu^II couple, thus allowing easy oxidation of the coordinated copper(II) by atmospheric oxygen.

Original language	English
Pages (from-to)	10038-10040
Number of pages	3
Journal	Inorganic Chemistry
Volume	46
Issue number	24
DOIs	https://doi.org/10.1021/ic701411y
State	Published - 26 Nov 2007
Externally published	Yes

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title = "New copper(II)/cyclic tetrapeptide system that easily oxidizes to copper(III) under atmospheric oxygen",

abstract = "A 13-membered ring cyclic tetrapeptide was synthesized by the solid-phase peptide synthesis method, and its copper(II) coordination properties were analyzed by optical spectroscopy, mass spectrometry, and electrochemistry. All collected data strongly support the presence, at alkaline pH, of a stable peptide/copper-(III) complex that is formed in solution by atmospheric dioxygen oxidation. On the basis of previous studies on cyclic peptide/copper systems, we suggest that the copper(III) ion is at the center of the ligand's cavity being coordinated to four deprotonated amide nitrogen atoms. This donor set would greatly lower the redox potential for the CuIII/CuII couple, thus allowing easy oxidation of the coordinated copper(II) by atmospheric oxygen.",

author = "Alessandro Pratesi and Piero Zanello and Gianluca Giorgi and Luigi Messori and Franco Laschi and Angela Casini and Maddalena Corsini and Chiara Gabbiani and Marco Orfei and Claudia Rosani and Mauro Ginanneschi",

year = "2007",

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doi = "10.1021/ic701411y",

language = "English",

volume = "46",

pages = "10038--10040",

journal = "Inorganic Chemistry",

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TY - JOUR

T1 - New copper(II)/cyclic tetrapeptide system that easily oxidizes to copper(III) under atmospheric oxygen

AU - Pratesi, Alessandro

AU - Zanello, Piero

AU - Giorgi, Gianluca

AU - Messori, Luigi

AU - Laschi, Franco

AU - Casini, Angela

AU - Corsini, Maddalena

AU - Gabbiani, Chiara

AU - Orfei, Marco

AU - Rosani, Claudia

AU - Ginanneschi, Mauro

PY - 2007/11/26

Y1 - 2007/11/26

N2 - A 13-membered ring cyclic tetrapeptide was synthesized by the solid-phase peptide synthesis method, and its copper(II) coordination properties were analyzed by optical spectroscopy, mass spectrometry, and electrochemistry. All collected data strongly support the presence, at alkaline pH, of a stable peptide/copper-(III) complex that is formed in solution by atmospheric dioxygen oxidation. On the basis of previous studies on cyclic peptide/copper systems, we suggest that the copper(III) ion is at the center of the ligand's cavity being coordinated to four deprotonated amide nitrogen atoms. This donor set would greatly lower the redox potential for the CuIII/CuII couple, thus allowing easy oxidation of the coordinated copper(II) by atmospheric oxygen.

AB - A 13-membered ring cyclic tetrapeptide was synthesized by the solid-phase peptide synthesis method, and its copper(II) coordination properties were analyzed by optical spectroscopy, mass spectrometry, and electrochemistry. All collected data strongly support the presence, at alkaline pH, of a stable peptide/copper-(III) complex that is formed in solution by atmospheric dioxygen oxidation. On the basis of previous studies on cyclic peptide/copper systems, we suggest that the copper(III) ion is at the center of the ligand's cavity being coordinated to four deprotonated amide nitrogen atoms. This donor set would greatly lower the redox potential for the CuIII/CuII couple, thus allowing easy oxidation of the coordinated copper(II) by atmospheric oxygen.

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U2 - 10.1021/ic701411y

DO - 10.1021/ic701411y

M3 - Article

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AN - SCOPUS:37249055962

SN - 0020-1669

VL - 46

SP - 10038

EP - 10040

JO - Inorganic Chemistry

JF - Inorganic Chemistry

IS - 24

ER -

New copper(II)/cyclic tetrapeptide system that easily oxidizes to copper(III) under atmospheric oxygen

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