ArticleAngewandte Chemie (International ed. in English)2021
Engineering Regioselectivity of a P450 Monooxygenase Enables the Synthesis of Ursodeoxycholic Acid via 7β-Hydroxylation of Lithocholic Acid.
Article in Angewandte Chemie (International ed. in English), 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 20 papers.
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20 citing papers in PubMed, 70 citations in OpenAlex.
- Improved catalytic efficiency of P450 OleP for converting lithocholic acid into murideoxycholic and ursodeoxycholic acids through semi-rational and rational design.Synthetic and systems biotechnology · 2027Article
- Engineering a heme-dependent tryptophan hydroxylase pathway inSynthetic and systems biotechnology · 2026Article
- Biosynthetic mechanism and ecological function of chirality in Solanum steroidal alkaloids.Nature communications · 2026Article
- Article
- Chicken Manure as a Sustainable Bile Acid Source for Biotechnological Applications.Microbial biotechnology · 2025Article
- Advances in Pharmacological Activities, Biosynthesis, and Structural Modification of Ursodeoxycholic Acid (UDCA): A Review.Drug design, development and therapy · 2025Review
- Enhancing substrate specificity of microbial transglutaminase for precise nanobody labeling.Synthetic and systems biotechnology · 2025Article
- Microbial transformations of bile acids and their receptors in the regulation of metabolic dysfunction-associated steatotic liver disease.Liver research (Beijing, China) · 2023Review
- Optimization and Impurity Control Strategy for Lithocholic Acid Production Using Commercially Plant-Sourced Bisnoralcohol.ACS omega · 2023Article
- Development of HPLC-CAD method for simultaneous quantification of nine related substances in ursodeoxycholic acid and identification of two unknown impurities by HPLC-Q-TOF-MS.Journal of pharmaceutical and biomedical analysis · 2023Article
- HApplied and environmental microbiology · 2023Article
- Biological synthesis of ursodeoxycholic acid.Frontiers in microbiology · 2023Review
- Rational development of mycobacteria cell factory for advancing the steroid biomanufacturing.World journal of microbiology & biotechnology · 2022Review
- Oxygenating Biocatalysts for Hydroxyl Functionalisation in Drug Discovery and Development.ChemMedChem · 2022Review
- One-pot biosynthesis of 7β-hydroxyandrost-4-ene-3,17-dione from phytosterols by cofactor regeneration system in engineered mycolicibacterium neoaurum.Microbial cell factories · 2022Article
- Point Mutations at a Key Site Alter the Cytochrome P450 OleP Structural Dynamics.Biomolecules · 2021Article
- Enzymatic strategies for asymmetric synthesis.RSC chemical biology · 2021Review
- Recent trends in biocatalysis.Chemical Society reviews · 2021Review
- Enabling highly (Chemical science · 2021Article
- Engineering Regioselectivity of a P450 Monooxygenase Enables the Synthesis of Ursodeoxycholic Acid via 7β-Hydroxylation of Lithocholic Acid.Angewandte Chemie (International ed. in English) · 2021Article
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Authors and funding
11 authors at 3 institutions in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
We engineered the cytochrome P450 monooxygenase CYP107D1 (OleP) from Streptomyces antibioticus for the stereo- and regioselective 7β-hydroxylation of lithocholic acid (LCA) to yield ursodeoxycholic acid (UDCA). OleP was previously shown to hydroxylate testosterone at the 7β-position but LCA is exclusively hydroxylated at the 6β-position, forming murideoxycholic acid (MDCA). Structural and 3DM analysis, and molecular docking were used to identify amino acid residues F84, S240, and V291 as specificity-determining residues. Alanine scanning identified S240A as a UDCA-producing variant. A synthetic "small but smart" library based on these positions was screened using a colorimetric assay for UDCA. We identified a nearly perfectly regio- and stereoselective triple mutant (F84Q/S240A/V291G) that produces 10-fold higher levels of UDCA than the S240A variant. This biocatalyst opens up new possibilities for the environmentally friendly synthesis of UDCA from the biological waste product LCA.
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