ArticleAngewandte Chemie (International ed. in English)2020
Regio- and Stereoselective Steroid Hydroxylation at C7 by Cytochrome P450 Monooxygenase Mutants.
Article in Angewandte Chemie (International ed. in English), 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 37 papers.
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Who cites it
37 citing papers in PubMed, 127 citations in OpenAlex.
- P450 engineering via structure-guided rational design achieves high C21-selectivity and bioconversion in steroid biosynthesis.Synthetic and systems biotechnology · 2026Article
- Expanding the Biocatalytic Toolbox: A Singular P450 Enzyme Efficiently Produces Diverse Pharmaceutical Metabolites.ACS omega · 2026Article
- Rank-guided learning accelerates automated enzyme engineering.Nature communications · 2026Article
- Comprehensive Profiling of 6α-Chloro-Testosterone Metabolism in Human Urine Using Gas Chromatography-Mass Spectrometry.Drug testing and analysis · 2026Article
- Article
- Regioselective Sesquiterpene Hydroxylation Directed by Tunnel Remodeling in Rieske Oxygenases.JACS Au · 2026Article
- A Dynamic Gate Enables Regioselective Hydroxylation of Free Arginine by a Non-Canonical Heme Enzyme.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2026Article
- Divergent evolution of fungal P450 monooxygenase unlocks simultaneous access to C12β and C15α oxyfunctionalization of steroids.Nature communications · 2025Article
- Steroid Hydroxylation by Mutant Cytochrome P450 BM3-LG23 Using Two Expression Chassis.International journal of molecular sciences · 2025Article
- Regulating the N-oxidation selectivity of P450BM3 monooxygenases for N-heterocycles through computer-assisted structure-guided design.Nature communications · 2025Article
- SubTuner leverages physics-based modeling to complement AI in enzyme engineering toward non-native substrates.Chem catalysis · 2025Article
- Structure-Function Analysis of the Self-Sufficient CYP102 Family Provides New Insights into Their Biochemistry.International journal of molecular sciences · 2025Article
- Biosynthesis of eriodictyol in citrus waster by endowing P450BM3 activity of naringenin hydroxylation.Applied microbiology and biotechnology · 2024Article
- Functional characterization and unraveling the structural determinants of novel steroid hydroxylase CYP154C7 fromHeliyon · 2024Article
- Regioselective and enantioselective propargylic hydroxylations catalyzed by P450tol monooxygenases.Bioresources and bioprocessing · 2024Article
- Choose Your Own Adventure: A Comprehensive Database of Reactions Catalyzed by Cytochrome P450 BM3 Variants.ACS catalysis · 2024Review
- Identification of a Gene Encoding a New Fungal Steroid 7-Hydroxylase and Its Functional Characterization inInternational journal of molecular sciences · 2023Article
- Biosynthesis of High-Active Hemoproteins by the Efficient Heme-Supply Pichia Pastoris Chassis.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2023Article
- Charting the Evolution of Chemoenzymatic Strategies in the Syntheses of Complex Natural Products.Journal of the American Chemical Society · 2023Review
- Non-Native Site-Selective Enzyme Catalysis.Chemical reviews · 2023Review
Corrections and comments
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Authors and funding
12 authors at 7 institutions in 5 countries.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Steroidal C7β alcohols and their respective esters have shown significant promise as neuroprotective and anti-inflammatory agents to treat chronic neuronal damage like stroke, brain trauma, and cerebral ischemia. Since C7 is spatially far away from any functional groups that could direct C-H activation, these transformations are not readily accessible using modern synthetic organic techniques. Reported here are P450-BM3 mutants that catalyze the oxidative hydroxylation of six different steroids with pronounced C7 regioselectivities and β stereoselectivities, as well as high activities. These challenging transformations were achieved by a focused mutagenesis strategy and application of a novel technology for protein library construction based on DNA assembly and USER (Uracil-Specific Excision Reagent) cloning. Upscaling reactions enabled the purification of the respective steroidal alcohols in moderate to excellent yields. The high-resolution X-ray structure and molecular dynamics simulations of the best mutant unveil the origin of regio- and stereoselectivity.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.