ArticleApplied and environmental microbiology2015
Reconstitution of the In Vitro Activity of the Cyclosporine-Specific P450 Hydroxylase from Sebekia benihana and Development of a Heterologous Whole-Cell Biotransformation System.
Article in Applied and environmental microbiology, 2015. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 17 papers.
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Who cites it
17 citing papers in PubMed, 45 citations in OpenAlex.
- A heme-dependent enzyme forms the hydrazine in the antibiotic negamycin.Nature chemical biology · 2025Article
- Functional analysis of the whole CYPome and Fdxome ofEngineering microbiology · 2024Article
- Biotransformation of selected secondary metabolites by Alternaria species and the pharmaceutical, food and agricultural application of biotransformation products.Natural products and bioprospecting · 2024Review
- Structure of methyltransferase RedM that forms the dimethylpyrrolinium of the bisindole reductasporine.The Journal of biological chemistry · 2024Article
- Biosynthesis of trialkyl-substituted aromatic polyketide NFAT-133 involves unusual P450 monooxygenase-mediating aromatization and a putative metallo-beta-lactamase fold hydrolase.Synthetic and systems biotechnology · 2023Article
- Diversification of phenolic glucosides by two UDP-glucosyltransferases featuring complementary regioselectivity.Microbial cell factories · 2022Article
- Three pairs of surrogate redox partners comparison for Class I cytochrome P450 enzyme activity reconstitution.Communications biology · 2022Article
- Heterologous redox partners supporting the efficient catalysis of epothilone B biosynthesis by EpoK in Schlegelella brevitalea.Microbial cell factories · 2020Article
- Cloning and heterologous expression of P450Lent4B11, a novel bacterial P450 gene, for hydroxylation of an antifungal agent sordaricin.The Journal of antibiotics · 2020Article
- Structure-guided manipulation of the regioselectivity of the cyclosporine A hydroxylase CYP-sb21 fromSynthetic and systems biotechnology · 2020Article
- Engineering cytochrome P450 enzyme systems for biomedical and biotechnological applications.The Journal of biological chemistry · 2020Review
- Hydroxylation of Steroids by a Microbial Substrate-Promiscuous P450 Cytochrome (CYP105D7): Key Arginine Residues for Rational Design.Applied and environmental microbiology · 2019Article
- Rational and semi-rational engineering of cytochrome P450s for biotechnological applications.Synthetic and systems biotechnology · 2018Review
- Deciphering the late steps of rifamycin biosynthesis.Nature communications · 2018Article
- Integrating multi-omics analyses of Nonomuraea dietziae to reveal the role of soybean oil in [(4'-OH)MeLeu]Microbial cell factories · 2017Article
- In vitro reconstitution of the cyclosporine specific P450 hydroxylases using heterologous redox partner proteins.Journal of industrial microbiology & biotechnology · 2017Article
- In vitro oxidative decarboxylation of free fatty acids to terminal alkenes by two new P450 peroxygenases.Biotechnology for biofuels · 2017Article
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Authors and funding
8 authors at 3 institutions in 2 countries.
Funding
No grant is acknowledged in the PubMed record.
Abstract
The cytochrome P450 enzyme CYP-sb21 from Sebekia benihana is capable of catalyzing the site-specific hydroxylation of the immunosuppressant cyclosporine (CsA), leading to the single product γ-hydroxy-N-methyl-l-Leu4-CsA (CsA-4-OH). Unlike authentic CsA, this hydroxylated CsA shows significantly reduced immunosuppressive activity while it retains a side effect of CsA, the hair growth stimulation effect. Although CYP-sb21 was previously identified to be responsible for CsA-specific hydroxylation in vivo, the in vitro activity of CYP-sb21 has yet to be established for a deeper understanding of this P450 enzyme and further reaction optimization. In this study, we reconstituted the in vitro activity of CYP-sb21 by using surrogate redox partner proteins of bacterial and cyanobacterial origins. The highest CsA site-specific hydroxylation activity by CYP-sb21 was observed when it was partnered with the cyanobacterial redox system composed of seFdx and seFdR from Synechococcus elongatus PCC 7942. The best bioconversion yields were obtained in the presence of 10% methanol as a cosolvent and an NADPH regeneration system. A heterologous whole-cell biocatalyst using Escherichia coli was also constructed, and the permeability problem was solved by using N-cetyl-N,N,N-trimethylammonium bromide (CTAB). This work provides a useful example for reconstituting a hybrid P450 system and developing it into a promising biocatalyst for industrial application.
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