Hydroxylation of carbazoles by Aspergillus flavus VKM F-1024

Carbazole was metabolized by Aspergillus flavus VKM F-1024 forming few monohydroxylated products. The structure of metabolites was determined by TLC, GC, MS and super(1)H NMR analyses. 3-Hydroxycarbazole was revealed as a major bioconversion product, 1-hydroxy- and 2-hydroxycarbazoles were observed...

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Bibliographic Details
Published in:FEMS microbiology letters 2004-06, Vol.235 (1), p.51-56
Main Authors: Lobastova, T G, Sukhodolskaya, G V, Nikolayeva, V M, Baskunov, B P, Turchin, K F, Donova, M V
Format: Article
Language:English
Subjects:
Aspergillus flavus
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Summary:Carbazole was metabolized by Aspergillus flavus VKM F-1024 forming few monohydroxylated products. The structure of metabolites was determined by TLC, GC, MS and super(1)H NMR analyses. 3-Hydroxycarbazole was revealed as a major bioconversion product, 1-hydroxy- and 2-hydroxycarbazoles were observed as minor products. In the presence of 1-benzoylindole, the hydroxylation position shifted toward preferable accumulation of 2-hydroxycarbazole and the formation of 2,6- and 2,7-dihydroxycarbazoles. This effect and microbial formation of these metabolites have never been reported before. At the conversion of N-acetyl- and N-benzoylcarbazoles, carbazole was the major product, while 1-, 2- and 3-monohydroxycarbazoles were formed in small amounts.
ISSN:0378-1097
DOI:10.1016/j.femsle.2004.04.008