Microorganisms as tools in modern chemistry: the biotransformation of 3-indolylacetonitrile and tryptamine by fungi

Abstract

Chemical reactions performed by microorganisms have been used as a modern tool in chemistry. In this work, the ability of the fungi Beauveria bassiana and Aspergillus niger to modify the chemical structure of indole compounds was studied. Beauveria bassiana was able to transform 3-indolylacetonitrile into 3-methylindole while Aspergillus niger transformed tryptamine into 5-hydroxyindole-3-acetamide. Interestingly, these fungi were able to perform both reduction and oxidation of the indole compounds fed, the oxidation occurring with improved levels of oxygen uptake. The results prove once more the versatility of microorganisms to perform a wide range of industrially attractive chemical reactions.

Biotransformation of Indole Derivatives by Mycelial Cultures

“…Interestingly, when 3-indoleacetic acid was fed to Pseudomonas sp. (Kieslich, 1976) and 3-indolylacetonitrile was fed to Beauveria bassiana (Boaventura et al, 2004) 3-methyl-indole was also obtained. The fact that microorganisms can metabolize different indole derivatives to 3-methyl-indole suggests that the synthesis of this compound by using a biological reagent can be successfully addressed and even improved.…”

Novel agents for enzymatic and fungal hydrolysis of stevioside

“…The use of biological systems, especially fungi and fungal enzymes to carry on chemical reactions, a process named biotransformation (13) attracted attention of chemists and microbiologists since such reactions are accomplished in smooth conditions, not only preserving chemical labile groups in the molecules but also being environment-friendly processes (3).…”

Biotransformation of a cage-like diels-alder adduct and derivatives by Mucor ramosissimus samutsevitsch

“…Bacteria and fungi have been used to produce chemicals, pharmaceuticals and perfumes during recent years (1). Whole microbial cells play an important role in organic synthesis field because of their diversity.…”

“…However, considering the great availability of useful microorganisms and the reactions that they can catalyze, the use of this strategy by industry is still modest (1). Therefore, the description of new useful reactions promoted by microbes is of great academic and industrial interest.…”