“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. [Figure not available: see fulltext.]
“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 / S. Arnaboldi, T. Benincori, R. Cirilli, S. Grecchi, L. Santagostini, F. Sannicolò, P.R. Mussini. - In: ANALYTICAL AND BIOANALYTICAL CHEMISTRY. - ISSN 1618-2642. - 408:26(2016 Oct), pp. 7243-7254. [10.1007/s00216-016-9852-x]
“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
S. Arnaboldi
;S. Grecchi;L. Santagostini;F. SannicolòPenultimo
;P.R. MussiniUltimo
2016
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. [Figure not available: see fulltext.]File | Dimensione | Formato | |
---|---|---|---|
art%3A10.1007%2Fs00216-016-9852-x.pdf
accesso riservato
Tipologia:
Publisher's version/PDF
Dimensione
2.18 MB
Formato
Adobe PDF
|
2.18 MB | Adobe PDF | Visualizza/Apri Richiedi una copia |
Errata COrrige ABC.pdf
accesso riservato
Descrizione: Erratum con una correzione ad una figura dell'articolo
Tipologia:
Altro
Dimensione
348.99 kB
Formato
Adobe PDF
|
348.99 kB | Adobe PDF | Visualizza/Apri Richiedi una copia |
216_2016_9852_MOESM1_ESM.pdf
accesso riservato
Descrizione: Supporting information
Tipologia:
Altro
Dimensione
503.52 kB
Formato
Adobe PDF
|
503.52 kB | Adobe PDF | Visualizza/Apri Richiedi una copia |
Pubblicazioni consigliate
I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.