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

被引：22

作者：

Bernini, Roberta ^{[1
]}

Barontini, Maurizio ^{[1
]}

Crisante, Fernanda ^{[1
]}

Ginnasi, Maria Cristina ^{[1
]}

Saladino, Raffaele ^{[1
]}

机构：

[1] Univ Tuscia, Dipartimento Agrobiol & Agrochim, I-01100 Viterbo, Italy

来源：

TETRAHEDRON LETTERS | 2009年 / 50卷 / 47期

关键词：

3,4-Dihydroxyphenylalanine (DOPA); Catechol moiety; IBX; Polymer-supported IBX (IBX polystyrene); Regioselective aromatic hydroxylation; IODOXYBENZOIC ACID IBX; SIDE-CHAIN; AMINO-ACIDS; CONVENIENT SYNTHESIS; PROTEINS; ADHESIVE; ALCOHOLS; REAGENT; 3,4-DIHYDROXYPHENYLALANINE; TRANSFORMATION;

D O I：

10.1016/j.tetlet.2009.09.034

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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

引用

页码：6519 / 6521

页数：3

共 59 条

[1] Oxidation of threonine residues with IBX reagents [J].