Jump to main content
Jump to site search

Issue 9, 2014
Previous Article Next Article

Towards the rational biosynthesis of substituted phenazines and phenoxazinones by laccases

Author affiliations

Abstract

Laccases are multi-copper oxidases that oxidise a wide range of substrates including phenol and aniline derivatives, which could be further involved in coupling reactions leading to the formation of dimeric and trimeric structures. This paper describes the enzyme-mediated dimerisation of several ortho and meta,para-disubstituted aromatic amines into phenazine (“head-to-tail” dimers) and phenoxazinone chromophores. The redox properties of substituted aromatic amines were studied by cyclic voltammetry and the kinetic constants of CotA and Trametes versicolor laccases were measured for selected aromatic amines. The structure of novel enzymatically synthesised phenazine and phenoxazinone dyes using CotA laccase was assessed by NMR and MS. Overall our data show that this enzymatic green process is an efficient alternative to the classic chemical oxidation of aromatic amines and phenols, with an impact on the broad field of applications of these heterocyclic compounds.

Graphical abstract: Towards the rational biosynthesis of substituted phenazines and phenoxazinones by laccases

Back to tab navigation

Supplementary files

Article information


Submitted
16 May 2014
Accepted
05 Jun 2014
First published
06 Jun 2014

Green Chem., 2014,16, 4127-4136
Article type
Paper
Author version available

Towards the rational biosynthesis of substituted phenazines and phenoxazinones by laccases

A. C. Sousa, M. C. Oliveira, L. O. Martins and M. P. Robalo, Green Chem., 2014, 16, 4127
DOI: 10.1039/C4GC00901K

Social activity

Search articles by author

Spotlight

Advertisements