Diamination by N-coupling using a commercial laccase

Nuclear diamination of p-hydrobenzoquinones with aromatic and aliphatic primary amines was catalysed by a commercial laccase, Denilite® II Base, from Novozymes. The amine and the p-hydrobenzoquinone was reacted under mild conditions (at room temperature and at 35°C) in a reaction vessel open to air...

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Bibliographic Details
Published in:Bioorganic & medicinal chemistry 2010-02, Vol.18 (4), p.1406-1414
Main Authors: Wellington, Kevin W., Steenkamp, Paul, Brady, Dean
Format: Article
Language:English
Subjects:
Amination
Benzoquinones - chemistry
Biocatalysis
Bioconversions. Hemisynthesis
Biological and medical sciences
Biotechnology
Denilite® II Base
Diaminobenzoquinones
Fundamental and applied biological sciences. Psychology
Green chemistry
Laccase
Laccase - chemistry
Magnetic Resonance Spectroscopy
Methods. Procedures. Technologies
Oxidative enzymes
p-Benzoquinones
p-Hydrobenzoquinones
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Summary:Nuclear diamination of p-hydrobenzoquinones with aromatic and aliphatic primary amines was catalysed by a commercial laccase, Denilite® II Base, from Novozymes. The amine and the p-hydrobenzoquinone was reacted under mild conditions (at room temperature and at 35°C) in a reaction vessel open to air in the presence of laccase and a co-solvent to afford, exclusively, the diaminated p-benzoquinone. These compounds may have potential antiallergic, antibiotic, anticancer, antifungal, antiviral and/or 5-lipoxygenase inhibiting activity. Nuclear diamination of p-hydrobenzoquinones with aromatic and aliphatic primary amines was catalysed by an immobilised commercial laccase, Denilite® II Base, from Novozymes. The amine and the p-hydrobenzoquinone was reacted under mild conditions (at room temperature and at 35°C) in a reaction vessel open to air in the presence of laccase and a co-solvent to afford, exclusively, the diaminated p-benzoquinone. These compounds may have potential antiallergic, antibiotic, anticancer, antifungal, antiviral and/or 5-lipoxygenase inhibiting activity.
ISSN:0968-0896
1464-3391
DOI:10.1016/j.bmc.2010.01.025