Regioselective synthesis of 3-hydroxyorthanilic acid and its biotransformation into a novel phenoxazinone dye by use of laccase

被引：50

作者：

Bruyneel, Frederic ^{[1
]}

Enaud, Estelle ^{[2
]}

Billottet, Ludovic ^{[1
]}

Vanhulle, Sophie ^{[2
]}

Marchand-Brynaert, Jacqueline ^{[1
]}

机构：

[1] Univ Catholique Louvain, Organ & Med Chem Unit CHOM, B-1348 Louvain, Belgium

[2] Univ Catholique Louvain, Microbiol Unit, MBLA, B-1348 Louvain, Belgium

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2008年 / 2008卷 / 01期

关键词：

laccase; phenoxazinone; lithiation; biotransformation; aromatic sulfonation reaction;

D O I：

10.1002/ejoc.200700865

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A natural phenoxazinone derivative, cinnabarinic acid (2, CA, R = CO2H), could be obtained in vitro with the aid of purified laccase from the fungi Pycnoporus cinnabarinus by oxidative dimerization of 3-hydroxyanthranilic acid (1, 3-HAA, R = CO2H). With the aim of gaining access to a new class of water-soluble chromophores and potential bioactive molecules, the regioselective sulfonation of 2-hydroxyanihne was investigated. Straightforward insertion of a sulfonate group into a carbon-metal bond provided an efficient and selective process for the synthesis of 3-hydroxyorthanilic acid (3, 3-HOA, R = SO3H). This sulfonated compound was then subjected to laccase oxidation in order to mimic the cinnabarinic acid synthesis. A practical HPLC method to study the oxidized products was developed, and the major product of biotransformation - namely 2-aniino-3-oxo-3H-phenoxazin-1,9-disulfonic acid (4, LAO, R = SO3H) - was isolated and identified as the sulfonate analogue of cinnabarinic acid. ((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008).

引用

页码：70 / 79

页数：10

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