Trimerisation of indole through laccase catalysis

被引：64

作者：

Ganachaud, Chrystelle ^{[1
]}

Garfagnoli, Vanessa ^{[1
]}

Tron, Thierry ^{[1
]}

Iacazio, Gilles ^{[1
]}

机构：

[1] Aix Marseille Univ, Fac Sci & Tech St Jerome, CNRS, Lab BiosCiences,FRE 3005, F-13397 Marseille 20, France

来源：

TETRAHEDRON LETTERS | 2008年 / 49卷 / 15期

关键词：

laccase; indole; TEMPO; biocatalysis; oxidation; green chemistry;

D O I：

10.1016/j.tetlet.2008.02.021

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Indole is cleanly bioconverted into a trimer upon laccase action. The formed compound has been identified as 2,2-bis(3'-indolyl)indoxyl (1) by X-ray diffraction study. Optimisation of the reaction through the use of dioxygen overpressure and TEMPO as mediator allowed a yield of more than 50% of isolated product for 1.2,2-Bis(3'-indolyl)indoxyl is a natural compound that has been isolated from bacterial sources. However, this is the first report on a clearly identified enzyme that could be involved in its (bio)synthesis. A mechanism, based on the initial formation of a transient indole hydroperoxide, is proposed to account for the faccase catalysed synthesis of 1. (C) 2008 Elsevier Ltd. All rights reserved.

引用

页码：2476 / 2478

页数：3

共 13 条

[1] Promoting laccase activity towards non-phenolic substrates: a mechanistic investigation with some laccase-mediator systems [J].