Biotransformation of 3-keto-androstanes by Gongronella butleri VKM F-1033
| Autor: | Andrei Shutov, V. V. Fokina, G. V. Sukhodolskaya, Vjacheslav V. Kollerov, Marina V. Donova |
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| Rok vydání: | 2008 |
| Předmět: |
Strain (chemistry)
Bioconversion Stereochemistry Process Chemistry and Technology medicine.medical_treatment Bioengineering Biochemistry High-performance liquid chromatography Catalysis Steroid Hydroxylation chemistry.chemical_compound Column chromatography chemistry Biotransformation medicine Incubation |
| Zdroj: | Journal of Molecular Catalysis B: Enzymatic. 55:61-68 |
| ISSN: | 1381-1177 |
| DOI: | 10.1016/j.molcatb.2008.01.009 |
| Popis: | The activity of Gongronella butleri VKM F-1033 towards androst-4-ene-3,17-dione (AD), androsta-1,4-diene-3,17-dione (ADD) and 9α-hydroxyandrost-4-ene-3,17-dione (9α-OH-AD) was studied. Bioconversion products were purified by column chromatography and preparative TLC, and identified by HPLC, mass-spectrometry and 1H NMR spectroscopy. The 7α-hydroxy-AD and 14α-hydroxy-AD were revealed as major products from AD, while 7β-, 6α-, 6β-hydroxylated AD derivatives were observed in small amounts. The presence of 1(2)-double bond in ADD molecule resulted in the accumulation of 14α-, 6β- and 7β-hydroxylated ADD derivatives, whereas no 7α-hydroxy steroid was formed from ADD. Along with hydroxylation, 17-ketone reduction was observed during AD and ADD bioconversion. Unlike other fungal biocatalysts, the strain carried out neither 1(2)-dehydrogenation of AD, nor 1(2)-hydrogenation of ADD. During incubation with 9α-OH-AD, two products, 9α, 14α-dihydroxy-AD and 6β, 9α-dihydroxy-AD were revealed. The results demonstrate the dependence of hydroxylation position on the structure of steroid nucleus. |
| Databáze: | OpenAIRE |
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