title: "Inherently chiral" thiophene-based electrodes at work: a screening of enantioselection ability toward a series of pharmaceutically relevant phenolic or catecholic amino acids, amino esters, and amine.
abstract: "Inherently chiral" thiophene-based electroactive oligomer films have recently been shown to exhibit outstanding chirality manifestations. One of the most exciting among them is an unprecedented enantioselection ability as electrode surfaces. In fact, in preliminary chiral voltammetry experiments, the new electrodes have been shown to both discriminate the enantiomers of chiral probes (either enantiopure or in a mixture, in terms of large differences in peak potentials) and quantify them (in terms of linear dynamic ranges in peak currents), without the need for preliminary separation steps. Such ability has now been tested on a series of chiral DOPA-related molecules, from phenolic amino acid tyrosine (together with its methyl ester) to catecholic amino acid DOPA (together with its methyl ester), to catecholamine epinephrine (adrenaline). The wide-range enantioselectivity of the new inherently chiral electrode surfaces is fully confirmed, as large peak potential differences are obtained for probe enantiomers of the whole series working in common aqueous buffers. Moreover, interesting modulating effects on enantiodiscrimination can be observed as a function of both molecular structure and pH. Graphical abstract Inherently chiral thiophene-based electrodes at work with pharmaceutically relevant probes.
authors.affiliation: Dipartimento di Chimica, Università degli Studi di Milano, Via Golgi 19, 20133, Milan, Italy. serena.arnaboldi@unimi.it.
authors.forename: Serena
authors.initials: S
authors.lastname: Arnaboldi
authors.affiliation: Dipartimento di Scienza e Alta Tecnologia, Università degli Studi dell'Insubria, Via Valleggio 11, 22100, Como, Italy.
authors.forename: Tiziana
authors.initials: T
authors.lastname: Benincori
authors.affiliation: Dipartimento del Farmaco, Istituto Superiore di Sanità, Viale Regina Elena 299, 00161, Rome, Italy.
authors.forename: Roberto
authors.initials: R
authors.lastname: Cirilli
authors.affiliation: Dipartimento di Chimica, Università degli Studi di Milano, Via Golgi 19, 20133, Milan, Italy.
authors.forename: Sara
authors.initials: S
authors.lastname: Grecchi
authors.affiliation: Dipartimento di Chimica, Università degli Studi di Milano, Via Golgi 19, 20133, Milan, Italy.
authors.forename: Laura
authors.initials: L
authors.lastname: Santagostini
authors.affiliation: Dipartimento di Chimica, Università degli Studi di Milano, Via Golgi 19, 20133, Milan, Italy.
authors.forename: Francesco
authors.initials: F
authors.lastname: Sannicolò
authors.affiliation: Dipartimento di Chimica, Università degli Studi di Milano, Via Golgi 19, 20133, Milan, Italy. patrizia.mussini@unimi.it.
authors.forename: Patrizia R
authors.initials: PR
authors.lastname: Mussini
mesh_terms: D000588:Amines / Q000302:isolation & purification; D000596:Amino Acids / Q000302:isolation & purification*; D002396:Catechols / Q000302:isolation & purification; D004295:Dihydroxyphenylalanine / Q000302:isolation & purification*; D055664:Electrochemical Techniques / Q000379:methods*; D004566:Electrodes; D004837:Epinephrine / Q000302:isolation & purification*; D004952:Esters / Q000302:isolation & purification; D010636:Phenols / Q000302:isolation & purification; D013237:Stereoisomerism; D013876:Thiophenes / Q000737:chemistry*; D014443:Tyrosine / Q000302:isolation & purification*
chemical_list: D000588:Amines; D000596:Amino Acids; D002396:Catechols; D004952:Esters; D010636:Phenols; D013876:Thiophenes; D014443:Tyrosine; D004295:Dihydroxyphenylalanine; C034221:catechol; D004837:Epinephrine
keywords: Adrenaline; Chiral electroanalysis; Chiral electrodes; Chiral voltammetry; DOPA; Tyrosine