An efficient route to 3,4-dihydroxylphenylalanine (DOPA) and DOPA peptides was described by oxidation of L-tyrosine and L-tyrosine derivatives with 2-iodoxybenzoic acid (IBX). DOPA was obtained after an situ reduction of the corresponding ortho-quinone with sodium dithionite. Oxidation reactions proceeded in good yields and high chemo- and regio-selectivity. The chirality of the DOPA residue was retained under the reaction conditions. The efficiency and the selectivity of the reaction were successfully tested using recyclable polymer-supported IBX.

A novel and efficient synthesis of DOPA and DOPA peptides by oxidation of tyrosine residues with IBX / Roberta, Bernini; Maurizio, Barontini; Crisante, Fernanda; Maria Cristina, Ginnasi; Raffaele, Saladino. - In: TETRAHEDRON LETTERS. - ISSN 0040-4039. - STAMPA. - 50:47(2009), pp. 6519-6521. [10.1016/j.tetlet.2009.09.034]

A novel and efficient synthesis of DOPA and DOPA peptides by oxidation of tyrosine residues with IBX

CRISANTE, Fernanda;
2009

Abstract

An efficient route to 3,4-dihydroxylphenylalanine (DOPA) and DOPA peptides was described by oxidation of L-tyrosine and L-tyrosine derivatives with 2-iodoxybenzoic acid (IBX). DOPA was obtained after an situ reduction of the corresponding ortho-quinone with sodium dithionite. Oxidation reactions proceeded in good yields and high chemo- and regio-selectivity. The chirality of the DOPA residue was retained under the reaction conditions. The efficiency and the selectivity of the reaction were successfully tested using recyclable polymer-supported IBX.
2009
3; 4-dihydroxyphenylalanine (dopa); catechol moiety; ibx; polymer-supported ibx (ibx polystyrene); regioselective aromatic hydroxylation
01 Pubblicazione su rivista::01a Articolo in rivista
A novel and efficient synthesis of DOPA and DOPA peptides by oxidation of tyrosine residues with IBX / Roberta, Bernini; Maurizio, Barontini; Crisante, Fernanda; Maria Cristina, Ginnasi; Raffaele, Saladino. - In: TETRAHEDRON LETTERS. - ISSN 0040-4039. - STAMPA. - 50:47(2009), pp. 6519-6521. [10.1016/j.tetlet.2009.09.034]
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11573/338432
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