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.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.