Latest development in the synthesis of ursodeoxycholic acid (UDCA): a critical review

Fabio Tonin and Isabel W. C. E. Arends
Beilstein J. Org. Chem. 2018, 14, 470–483. https://doi.org/10.3762/bjoc.14.33

Supporting Information

Supporting Information features Figure S1 relative to the C7 dehydroxylation mechanism of hydroxysteroids and Figure S2 relative to the postulated biochemical pathway for the C12 dehydroxylation.

Supporting Information File 1: Supporting Figures S1 and S2.
Format: PDF Size: 611.6 KB Download

Cite the Following Article

Latest development in the synthesis of ursodeoxycholic acid (UDCA): a critical review
Fabio Tonin and Isabel W. C. E. Arends
Beilstein J. Org. Chem. 2018, 14, 470–483. https://doi.org/10.3762/bjoc.14.33

How to Cite

Tonin, F.; Arends, I. W. C. E. Beilstein J. Org. Chem. 2018, 14, 470–483. doi:10.3762/bjoc.14.33

Download Citation

Citation data can be downloaded as file using the "Download" button or used for copy/paste from the text window below.
Citation data in RIS format can be imported by all major citation management software, including EndNote, ProCite, RefWorks, and Zotero.

Presentation Graphic

Picture with graphical abstract, title and authors for social media postings and presentations.
Format: PNG Size: 759.5 KB Download

Citations to This Article

Up to 20 of the most recent references are displayed here.

Scholarly Works

  • Zeng, C.; Liu, X.; Sun, C.; Xu, X.; Peng, L. High Enantioselective and Large-Scale Production of Ursodeoxycholic Acid by Combination of Pd- and Hydroxysteroid Dehydrogenase-Catalyzed Hydrogenation. Organic Process Research & Development 2024. doi:10.1021/acs.oprd.4c00057
  • Zhou, Z.-R.; Liu, F.; Li, S.; Dong, C.-Z.; Zhang, L. A fungal P450 enzyme from Fusarium equiseti HG18 with 7β-hydroxylase activity in biosynthesis of ursodeoxycholic acid. The Journal of steroid biochemistry and molecular biology 2024, 240, 106507. doi:10.1016/j.jsbmb.2024.106507
  • France, S. P.; Lindsey, E. A.; McInturff, E. L.; Berritt, S.; Carney, D. W.; DeForest, J. C.; Fink, S. J.; Flick, A. C.; Gibson, T. S.; Gray, K.; Johnson, A. M.; Leverett, C. A.; Liu, Y.; Mahapatra, S.; Watson, R. B. Synthetic Approaches to the New Drugs Approved During 2022. Journal of medicinal chemistry 2024. doi:10.1021/acs.jmedchem.3c02374
  • d'Oelsnitz, S.; Stofel, S. K.; Love, J. D.; Ellington, A. D. Snowprint: a predictive tool for genetic biosensor discovery. Communications biology 2024, 7, 163. doi:10.1038/s42003-024-05849-8
  • Liu, S.; Yang, S.; Blazekovic, B.; Li, L.; Zhang, J.; Wang, Y. Bioactivities, Mechanisms, Production, and Potential Application of Bile Acids in Preventing and Treating Infectious Diseases. Engineering 2024. doi:10.1016/j.eng.2023.11.017
  • Lee, J.; Park, J.-S. The gut microbiome predicts response to UDCA/CDCA treatment in gallstone patients: comparison of responders and non-responders. Scientific reports 2024, 14, 2534. doi:10.1038/s41598-024-53173-2
  • Qu, Y.; Gong, X.; Zhao, Z.; Zhang, Z.; Zhang, Q.; Huang, Y.; Xie, Q.; Liu, Y.; Wei, J.; Du, H. Establishment and Validation of Novel Prognostic Subtypes in Hepatocellular Carcinoma Based on Bile Acid Metabolism Gene Signatures Using Bulk and Single-Cell RNA-Seq Data. International journal of molecular sciences 2024, 25, 919. doi:10.3390/ijms25020919
  • Liu, W.; Shen, W.; Xia, Y.; Chen, X.; Yang, H. Boosting the Biosynthesis of Ursodeoxycholic Acid via a Novel 7β-Hydroxysteroid Dehydrogenase from Olsenella sp. and Biotransformation Systematic Optimization. ACS Sustainable Chemistry & Engineering 2024, 12, 1333–1342. doi:10.1021/acssuschemeng.3c07948
  • Zheng, M.; Lin, Z.; Lin, S.; Qu, X. Chemoenzymatic Synthesis of Steroidal Products: Recent Advances. European Journal of Organic Chemistry 2024, 27. doi:10.1002/ejoc.202301066
  • Song, Y.; Lau, H. C.; Zhang, X.; Yu, J. Bile acids, gut microbiota, and therapeutic insights in hepatocellular carcinoma. Cancer biology & medicine 2023, 21, 1–19. doi:10.20892/j.issn.2095-3941.2023.0394
  • Wang, M.-Q.; You, Z.-N.; Yang, B.-Y.; Xia, Z.-W.; Chen, Q.; Pan, J.; Li, C.-X.; Xu, J.-H. Machine-Learning-Guided Engineering of an NADH-Dependent 7β-Hydroxysteroid Dehydrogenase for Economic Synthesis of Ursodeoxycholic Acid. Journal of agricultural and food chemistry 2023, 71, 19672–19681. doi:10.1021/acs.jafc.3c06339
  • Yang, J.; Chen, X.; Liu, T.; Shi, Y. Potential role of bile acids in the pathogenesis of necrotizing enterocolitis. Life sciences 2023, 336, 122279. doi:10.1016/j.lfs.2023.122279
  • Kim, S.; Jo, H.; Lee, S.; Yang, M.; Jun, H.; Lee, Y.; Kim, G.-W.; Lee, D. Targeted echogenic and anti-inflammatory polymeric prodrug nanoparticles for the management of renal ischemia/reperfusion injury. Journal of controlled release : official journal of the Controlled Release Society 2023, 363, 574–584. doi:10.1016/j.jconrel.2023.10.004
  • Pan, Y.; Tang, S.; Zhu, L.; Lou, D.; Tan, J.; Wang, B. Design of St-2-2 7α-HSDH mutants for altering substrate preference and thermostability. Molecular Catalysis 2023, 548, 113423. doi:10.1016/j.mcat.2023.113423
  • Kim, O. Y.; Lee, S. Y.; Lee, D. Y.; Hur, S. J. Developing a procedure to extract chenodeoxycholic acid and synthesize ursodeoxycholic acid from pig by-products. Heliyon 2023, 9, e18313. doi:10.1016/j.heliyon.2023.e18313
  • Liu, T.; Wang, J.-S. Ursodeoxycholic acid administration did not reduce susceptibility to SARS-CoV-2 infection in children. Liver international : official journal of the International Association for the Study of the Liver 2023, 43, 1950–1954. doi:10.1111/liv.15660
  • d'Oelsnitz, S.; Stofel, S. K.; Ellington, A. D. Snowprint: a predictive tool for genetic biosensor discovery. Cold Spring Harbor Laboratory 2023. doi:10.1101/2023.04.29.538814
  • Huang, Y.; Lu, H.; Li, Z.; Zeng, Y.; Xu, Q.; Wu, Y. 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 2023, 229, 115357. doi:10.1016/j.jpba.2023.115357
  • Yu, L.; Liu, Y.; Wang, S.; Zhang, Q.; Zhao, J.; Zhang, H.; Narbad, A.; Tian, F.; Zhai, Q.; Chen, W. Cholestasis: exploring the triangular relationship of gut microbiota-bile acid-cholestasis and the potential probiotic strategies. Gut microbes 2023, 15, 2181930. doi:10.1080/19490976.2023.2181930
  • Song, P.; Zhang, X.; Feng, W.; Xu, W.; Wu, C.; Xie, S.; Yu, S.; Fu, R. Biological synthesis of ursodeoxycholic acid. Frontiers in microbiology 2023, 14, 1140662. doi:10.3389/fmicb.2023.1140662

Patents

  • CASTALDI MICHELE; CASTALDI GRAZIANO. MICROBIOLOGICAL PROCESS FOR THE PREPARATION OF URSOCHOLIC ACID. WO 2022023155 A1, Feb 3, 2022.
  • BORNSCHEUER UWE; GROBE SASCHA; HANNEVIK EMIL; BAYER THOMAS; BADENHORST CHRISTOFFEL; BRUNDIEK HENRIKE; GROSSJOHANN BEATRICE. PROCESS FOR 7-BETA-HYDROXYLATION OF BILE ACID DERIVATIVES. EP 3933036 A1, Jan 5, 2022.
  • STAUNIG NICOLE; DONSBACH KAI OLIVER. PROCESS FOR HYDROXYLATING STEROIDS. WO 2021176068 A1, Sept 10, 2021.
  • STAUNIG NICOLE; DONSBACH KAI OLIVER. METHOD FOR HYDROXYLATION OF STEROIDS. EP 3875596 A1, Sept 8, 2021.
  • KIM HEE TAEK; RYU MI HEE; JUNG YE JEAN; SONG BONG KEUN; KANG KYOUNG HEE. METHOD FOR PRODUCING URSODEOXYCHOLIC ACID USING DEEP EUTECTIC SOLVENT. WO 2021085997 A1, May 6, 2021.
  • ENQUIST-NEWMAN MARIA; TOM ERIN; HO CLEO; SAVILE CHRISTOPHER; KUMAR ABHINAV; ESSER LAUREN; CHAN ANDREA; CLAY MICHAEL; PIGULA ADRIANNA; CHEN HSIANG-YUN. CELLS AND METHODS FOR THE PRODUCTION OF URSODEOXYCHOLIC ACID AND PRECURSORS THEREOF. WO 2020076819 A1, April 16, 2020.
Other Beilstein-Institut Open Science Activities