Forum for Science, Industry and Business

Sponsored by:     3M 
Search our Site:

 

Synthesis of opium alkaloids using electric current

28.06.2018

A selective electrochemical reaction enables the synthesis of thebaine and offers a solution to a long-standing synthetic challenge

Researchers at Johannes Gutenberg University Mainz (JGU) have mastered a nearly 50-year-old challenge of electrosynthetic chemistry, namely the electrochemical synthesis of thebaine. The chemists had set themselves this difficult task within the framework of a collaboration with the University of Münster.


The Mainz-based chemists investigated the oxidative key step in the biosynthesis of thebaine, codeine, and morphine using a simple and self-made electrochemical cell.

photo/©: Alexander Lipp

Thebaine is a component of the latex of the opium poppy and is named after the old designation of Luxor, i.e., the Ancient Egyptian city of Thebes. This opium alkaloid is the biosynthetic precursor of codeine and morphine and serves as the starting material for the industrial production of important pharmaceuticals, such as oxycodone or naloxone.

The key step in the biosynthesis of thebaine, codeine, and morphine involves a reaction known as oxidative coupling. For decades, researchers have been trying to mimic this transformation in the laboratory.

However, this oxidative coupling represents a considerable challenge because it can result in the formation of four different products, only one of which can be further converted into thebaine. Hence, in order to efficiently mimic this naturally occurring process, a highly selective reaction is mandatory.

For decades, chemists have attempted to accomplish a biomimetic synthesis of thebaine using conventional oxidants. However, large quantities of these often toxic reagents were required and undesired coupling products were obtained in most cases.

Electrochemistry is a technique that involves the transfer of electrons to or from molecules on the surface of electrodes immersed in a solution. Using this method, it is possible to perform reagent-free oxidations.

In fact, these environmentally benign processes only require electric current and avoid the production of chemical waste. So far, electrochemistry did not provide coupling products which could be transformed into thebaine, and its electrochemical synthesis remained a challenging task.

Alexander Lipp and Professor Till Opatz from the Institute of Organic Chemistry at JGU have now solved this long-standing problem. Their approach involved astute modification of the starting materials used in the oxidative coupling. With this, they have also paved the way for the future electrochemical synthesis of further opium alkaloids.

Other participants involved in the project were Professor Siegfried R. Waldvogel, also from the Institute of Organic Chemistry at Mainz University, and Professor Hans J. Schäfer from the University of Münster. The project was undertaken under the aegis of the Advanced Lab for Electrochemistry and Electroorganic Synthesis (ELYSION), financed by the Carl Zeiss Foundation.

Image:
http://www.uni-mainz.de/bilder_presse/09_orgchemie_opium_alkaloide.jpg
The Mainz-based chemists investigated the oxidative key step in the biosynthesis of thebaine, codeine, and morphine using a simple and self-made electrochemical cell.
photo/©: Alexander Lipp

Publication:
A. Lipp et al., A Regio‐ and Diastereoselective Anodic Aryl–Aryl Coupling in the Biomimetic Total Synthesis of (−)‐Thebaine, Angewandte Chemie International Edition, 22 May 2018,
DOI:10.1002/anie.201803887
https://onlinelibrary.wiley.com/doi/abs/10.1002/anie.201803887

Contact:
Professor Dr. Till Opatz
Institute of Organic Chemistry
Johannes Gutenberg University Mainz
55099 Mainz, GERMANY
phone +49 6131 39-22272 or 39-24443
fax +49 6131 39-22338
e-mail: opatz@uni-mainz.de
https://ak-opatz.chemie.uni-mainz.de/prof-dr-till-opatz/ [in German]

Related links:
https://doi.org/10.1002/anie.201806821 (Cover in Angewandte Chemie Int. Ed.)

Read more:
http://www.uni-mainz.de/presse/aktuell/5480_ENG_HTML.php – press release "Antidiabetic action of natural fatty acid derivatives not confirmed" (25 June 2018)
http://www.uni-mainz.de/presse/19700_ENG_HTML.php – press release "Wood instead of petroleum: New approach to producing chemical substances solely from renewable resources" (26 Oct. 2015)
http://www.uni-mainz.de/presse/19525_ENG_HTML.php – press release "Carl Zeiss Foundation donates EUR 850,000 to the Advanced Lab for Electrochemistry and Electroorganic Synthesis at Mainz University" (12 Aug. 2015)

Petra Giegerich | idw - Informationsdienst Wissenschaft

More articles from Life Sciences:

nachricht Study clarifies kinship of important plant group
05.08.2020 | Rheinische Friedrich-Wilhelms-Universität Bonn

nachricht Human cell-based test systems for toxicity studies: Ready-to-use Toxicity Assay (hiPSC)
05.08.2020 | Fraunhofer-Institut für Biomedizinische Technik IBMT

All articles from Life Sciences >>>

The most recent press releases about innovation >>>

Die letzten 5 Focus-News des innovations-reports im Überblick:

Im Focus: New Strategy Against Osteoporosis

An international research team has found a new approach that may be able to reduce bone loss in osteoporosis and maintain bone health.

Osteoporosis is the most common age-related bone disease which affects hundreds of millions of individuals worldwide. It is estimated that one in three women...

Im Focus: AI & single-cell genomics

New software predicts cell fate

Traditional single-cell sequencing methods help to reveal insights about cellular differences and functions - but they do this with static snapshots only...

Im Focus: TU Graz Researchers synthesize nanoparticles tailored for special applications

“Core-shell” clusters pave the way for new efficient nanomaterials that make catalysts, magnetic and laser sensors or measuring devices for detecting electromagnetic radiation more efficient.

Whether in innovative high-tech materials, more powerful computer chips, pharmaceuticals or in the field of renewable energies, nanoparticles – smallest...

Im Focus: Tailored light inspired by nature

An international research team with Prof. Cornelia Denz from the Institute of Applied Physics at the University of Münster develop for the first time light fields using caustics that do not change during propagation. With the new method, the physicists cleverly exploit light structures that can be seen in rainbows or when light is transmitted through drinking glasses.

Modern applications as high resolution microsopy or micro- or nanoscale material processing require customized laser beams that do not change during...

Im Focus: NYUAD astrophysicist investigates the possibility of life below the surface of Mars

  • A rover expected to explore below the surface of Mars in 2022 has the potential to provide more insights
  • The findings published in Scientific Reports, Springer Nature suggests the presence of traces of water on Mars, raising the question of the possibility of a life-supporting environment

Although no life has been detected on the Martian surface, a new study from astrophysicist and research scientist at the Center for Space Science at NYU Abu...

All Focus news of the innovation-report >>>

Anzeige

Anzeige

VideoLinks
Industry & Economy
Event News

“Conference on Laser Polishing – LaP 2020”: The final touches for surfaces

23.07.2020 | Event News

Conference radar for cybersecurity

21.07.2020 | Event News

Contact Tracing Apps against COVID-19: German National Academy Leopoldina hosts international virtual panel discussion

07.07.2020 | Event News

 
Latest News

Manifestation of quantum distance in flat band materials

05.08.2020 | Physics and Astronomy

Discovery shows promise for treating Huntington's Disease

05.08.2020 | Health and Medicine

Rock debris protects glaciers from climate change more than previously known

05.08.2020 | Earth Sciences

VideoLinks
Science & Research
Overview of more VideoLinks >>>