One-pot synthesis of human metabolites of SAR548304 by fungal peroxygenases.
@article{Kiebist2015OnepotSO, title={One-pot synthesis of human metabolites of SAR548304 by fungal peroxygenases.}, author={Jan Kiebist and W. Holla and J. Heidrich and Marzena Poraj-Kobielska and M. Sandvoss and Reiner Simonis and Glenn Gr{\"o}be and J. Atzrodt and M. Hofrichter and K. Scheibner}, journal={Bioorganic & medicinal chemistry}, year={2015}, volume={23 15}, pages={ 4324-32 } }
Unspecific peroxygenases (UPOs, EC 1.11.2.1) have proved to be stable oxygen-transferring biocatalysts for H2O2-dependent transformation of pharmaceuticals. We have applied UPOs in a drug development program and consider the enzymatic approach in parallel to a conventional chemical synthesis of the human metabolites of the bile acid reabsorption inhibitor SAR548304. Chemical preparation of N,N-di-desmethyl metabolite was realized by a seven-step synthesis starting from a late precursor of… CONTINUE READING
Topics from this paper
14 Citations
Synthesis of cyclophosphamide metabolites by a peroxygenase from Marasmius rotula for toxicological studies on human cancer cells
- Chemistry, Medicine
- AMB Express
- 2020
Selective synthesis of the human drug metabolite 5’-hydroxypropranolol by an evolved self-sufficient peroxygenase
- Chemistry
- 2018
- 21
- PDF
Benchmarking of laboratory evolved unspecific peroxygenases for the synthesis of human drug metabolites
- Chemistry
- 2019
- 9
A Peroxygenase from Chaetomium globosum Catalyzes the Selective Oxygenation of Testosterone
- Chemistry, Medicine
- Chembiochem : a European journal of chemical biology
- 2017
- 23
Fatty acid epoxidation by Collariella virescens peroxygenase and heme-channel variants
- Chemistry
- 2020
- 3
- PDF
Fungal Peroxygenases: A Phylogenetically Old Superfamily of Heme Enzymes with Promiscuity for Oxygen Transfer Reactions
- Chemistry
- 2020
- 10
Accessing Drug Metabolites via Transition-Metal Catalyzed C-H Oxidation: The Liver as Synthetic Inspiration.
- Chemistry, Medicine
- Angewandte Chemie
- 2016
- 29
Charged Tags for the Identification of Oxidative Drug Metabolites Based on Electrochemistry and Mass Spectrometry
- Chemistry, Medicine
- ChemistryOpen
- 2020
Oxidoreductases on their way to industrial biotransformations.
- Chemistry, Medicine
- Biotechnology advances
- 2017
- 92
- PDF
References
SHOWING 1-10 OF 55 REFERENCES
Preparation of human drug metabolites using fungal peroxygenases.
- Chemistry, Medicine
- Biochemical pharmacology
- 2011
- 53
- PDF
Preparation of labeled human drug metabolites and drug-drug interaction-probes with fungal peroxygenases.
- Chemistry, Medicine
- Journal of labelled compounds & radiopharmaceuticals
- 2013
- 14
Oxidative Cleavage of Diverse Ethers by an Extracellular Fungal Peroxygenase*
- Chemistry, Medicine
- The Journal of Biological Chemistry
- 2009
- 70
- PDF
Enzymatic one-pot conversion of cyclohexane into cyclohexanone: Comparison of four fungal peroxygenases
- Chemistry
- 2014
- 29
Selective hydroxylation of alkanes by an extracellular fungal peroxygenase
- Chemistry, Medicine
- The FEBS journal
- 2011
- 81
High-yield production of aromatic peroxygenase by the agaric fungus Marasmius rotula
- Biology, Medicine
- AMB Express
- 2011
- 57
Common and uncommon cytochrome P450 reactions related to metabolism and chemical toxicity.
- Chemistry, Medicine
- Chemical research in toxicology
- 2001
- 1,316
Mechanisms of cytochrome P450 substrate oxidation: MiniReview
- Chemistry, Medicine
- Journal of biochemical and molecular toxicology
- 2007
- 187