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

An efficient route to 3,4-dihydroxylphenylalanine (DOPA) and DOPA pept des was described by oxidation of L-tyrosine and L-tyrosine derivatives with 2-iodoxybenzoic acid (IBX) DOPA was obtained after ail Situ reduction of the corresponding ortho-Cl U I none with sodium dithionite. Oxidation reactions proceeded Ill 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 (C) 2009 Elsevier Ltd. All rights reserved