Whole-cell biotransformation with recombinant cytochrome P450 for the selective oxidation of Grundmann’s ketone

2014 ◽  
Vol 22 (20) ◽  
pp. 5586-5592 ◽  
Author(s):  
Alba Hernández-Martín ◽  
Clemens J. von Bühler ◽  
Florian Tieves ◽  
Susana Fernández ◽  
Miguel Ferrero ◽  
...  
Keyword(s):  
Cytochrome P450 ◽  
Selective Oxidation ◽  
Whole Cell ◽  
Whole Cell Biotransformation

CYP21-catalyzed production of the long-term urinary metandienone metabolite 17β-hydroxymethyl-17α-methyl-18-norandrosta-1,4,13-trien-3-one: a contribution to the fight against doping

2010 ◽  
Vol 391 (1) ◽  
Author(s):  
Andy Zöllner ◽  
Maria Kristina Parr ◽  
Călin-Aurel Drăgan ◽  
Stefan Dräs ◽  
Nils Schlörer ◽  
...  
Keyword(s):  
Cytochrome P450 ◽  
Reference Material ◽  
Anabolic Androgenic Steroids ◽  
Reference Substance ◽  
Cytochrome P450 Enzymes ◽  
Whole Cell ◽  
In Doping ◽  
Whole Cell Biotransformation ◽  
Androgenic Steroids

AbstractAnabolic-androgenic steroids are some of the most frequently misused drugs in human sports. Recently, a previously unknown urinary metabolite of metandienone, 17β-hydroxymethyl-17α-methyl-18-norandrosta-1,4,13-trien-3-one (20OH-NorMD), was discovered via LC-MS/MS and GC-MS. This metabolite was reported to be detected in urine samples up to 19 days after administration of metandienone. However, so far it was not possible to obtain purified reference material of this metabolite and to confirm its structure via NMR. Eleven recombinant strains of the fission yeastSchizosaccharomyces pombethat express different human hepatic or steroidogenic cytochrome P450 enzymes were screened for production of this metabolite in a whole-cell biotransformation reaction. 17,17-Dimethyl-18-norandrosta-1,4,13-trien-3-one, chemically derived from metandienone, was used as substrate for the bioconversion, because it could be converted to the final product in a single hydroxylation step. The obtained results demonstrate that CYP21 and to a lesser extent also CYP3A4 expressing strains can catalyze this steroid hydroxylation. Subsequent 5 l-scale fermentation resulted in the production and purification of 10 mg of metabolite and its unequivocal structure determination via NMR. The synthesis of this urinary metandienone metabolite viaS. pombe-based whole-cell biotransformation now allows its use as a reference substance in doping control assays.

Asymmetric reduction of a key intermediate of eslicarbazepine acetate using whole cell biotransformation in a biphasic medium

2012 ◽  
Vol 2 (8) ◽  
pp. 1602 ◽  
Author(s):  
Manpreet Singh ◽  
Sawraj Singh ◽  
Sateesh Deshaboina ◽  
Hare Krishnen ◽  
Richard Lloyd ◽  
...  
Keyword(s):  
Asymmetric Reduction ◽  
Eslicarbazepine Acetate ◽  
Whole Cell ◽  
Whole Cell Biotransformation ◽  
Biphasic Medium

scholarly journals Characterization of P450 FcpC, the Enzyme Responsible for Bioconversion of Diosgenone to Isonuatigenone in Streptomyces virginiae IBL-14

2009 ◽  
Vol 75 (12) ◽  
pp. 4202-4205 ◽  
Author(s):  
Wei Wang ◽  
Feng-Qing Wang ◽  
Dong-Zhi Wei
Keyword(s):  
Escherichia Coli ◽  
Electron Transfer ◽  
Cytochrome P450 ◽  
Cytochrome P450 Monooxygenase ◽  
P450 Monooxygenase ◽  
Whole Cell ◽  
Electron Transfer Chain ◽  
Streptomyces Virginiae ◽  
Transfer Chain

ABSTRACT A new cytochrome P450 monooxygenase, FcpC, from Streptomyces virginiae IBL-14 has been identified. This enzyme is found to be responsible for the bioconversion of a pyrano-spiro steroid (diosgenone) to a rare nuatigenin-type spiro steroid (isonuatigenone), which is a novel C-25-hydroxylated diosgenone derivative. A whole-cell P450 system was developed for the production of isonuatigenone via the expression of the complete three-component electron transfer chain in an Escherichia coli strain.

Glyoxylate Carboligase-based Whole-Cell Biotransformation of Formaldehyde into Ethylene Glycol via Glycolaldehyde

2021 ◽  
Author(s):  
Hye-Jin Jo ◽  
Jun-Hong Kim ◽  
Ye-Na Kim ◽  
Pil-Won Seo ◽  
Chae-Yun Kim ◽  
...  
Keyword(s):  
Ethylene Glycol ◽  
Whole Cell ◽  
Whole Cell Biotransformation

A novel biocatalytic system for the synthesis of the industrially relevant C2 chemicals (e.g., ethylene glycol (3)) from formaldehyde (1) was established. The biocatalytic system consisted of a newly discovered...

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