Terpenes are natural products that are often very difficult to synthesize in the laboratory. Chemists from the University of Basel have now developed a synthesis method that mimics nature. The decisive step takes place inside a molecular capsule, which enables the reaction. The findings were recently published in the journal Nature Catalysis.
Terpenes are the largest class of chemical compounds that are found in nature. They include, for example, many essential oils, steroids and clinically relevant substances such as the antimalarial drug artemisinin or the chemotherapy medication paclitaxel.
Despite increasingly refined synthesis methods, chemists have found it very difficult to synthesize these structurally complex compounds in the lab. The process often requires numerous, not always selective synthesis steps, and the yields tend to be low.
Nature points the way
The research group led by Professor Konrad Tiefenbacher from the University of Basel’s Department of Chemistry has now developed a synthesis concept for terpenes copied from nature.
The decisive step takes place in the cavity of a spherical compound – known as a molecular capsule. The resorcinarene capsule used has been known about for around 20 years but its catalytic effect has only very recently been described, by Tiefenbacher and others. In organic solvents, the capsule forms itself from six smaller, ring-shaped compounds with the help of hydrogen bonds.
In a similar way to nature, the researchers led by Tiefenbacher begin with a starting material for the synthesis, which is enclosed by the capsule. The capsule environment then enables the formation of the terpene. In addition, control elements previously integrated into the precursor help avoid unwanted side effects and direct the transformation towards the desired product.
The applicability of the concept was proven by the four-step synthesis of the natural product isolongifolene, with the formation of a ring-shaped terpene compound catalyzed by the capsule as the key step. This succeeded – when compared with conventional syntheses – in significantly fewer steps and with a good yield. Using labeled precursors and with the help of computer simulations, the Basel chemists were also able to clarify the reaction mechanism.
“Our next goal is to use capsules as an artificial enzyme in the creation of even more complex terpenes,” says Professor Tiefenbacher. “In order to do so, we must learn to better control the spatial arrangement of the precursor within the capsule, either by modifying the existing system or by developing new catalysts.” This may open up new ways of synthesizing terpene compounds that would otherwise not be readily accessible.
Prof. Dr. Konrad Tiefenbacher, University of Basel, Department of Chemistry, tel. +41 61 207 56 09, email: email@example.com
Qi Zhang, Jan Rinkel, Bernd Goldfuss, Jeroen S. Dickschat, Konrad Tiefenbacher
Sesquiterpene cyclizations catalysed inside the resorcinarene capsule and application in the short synthesis of isolongifolene and isolongifolenone
Nature Catalysis (2018), doi: 10.1038/s41929-018-0115-4
Reto Caluori | Universität Basel
Monitoring biodiversity with sound: how machines can enrich our knowledge
18.06.2019 | Georg-August-Universität Göttingen
Uncovering hidden protein structures
18.06.2019 | Universität Konstanz
The well-known representation of chemical elements is just one example of how objects can be arranged and classified
The periodic table of elements that most chemistry books depict is only one special case. This tabular overview of the chemical elements, which goes back to...
Light can be used not only to measure materials’ properties, but also to change them. Especially interesting are those cases in which the function of a material can be modified, such as its ability to conduct electricity or to store information in its magnetic state. A team led by Andrea Cavalleri from the Max Planck Institute for the Structure and Dynamics of Matter in Hamburg used terahertz frequency light pulses to transform a non-ferroelectric material into a ferroelectric one.
Ferroelectricity is a state in which the constituent lattice “looks” in one specific direction, forming a macroscopic electrical polarisation. The ability to...
Researchers at TU Graz calculate the most accurate gravity field determination of the Earth using 1.16 billion satellite measurements. This yields valuable knowledge for climate research.
The Earth’s gravity fluctuates from place to place. Geodesists use this phenomenon to observe geodynamic and climatological processes. Using...
Discovery by Brazilian and US researchers could change the classification of two species, which appear more akin to jellyfish than was thought.
The tube anemone Isarachnanthus nocturnus is only 15 cm long but has the largest mitochondrial genome of any animal sequenced to date, with 80,923 base pairs....
Researchers at Chalmers University of Technology, Sweden, have discovered a completely new way of capturing, amplifying and linking light to matter at the nanolevel. Using a tiny box, built from stacked atomically thin material, they have succeeded in creating a type of feedback loop in which light and matter become one. The discovery, which was recently published in Nature Nanotechnology, opens up new possibilities in the world of nanophotonics.
Photonics is concerned with various means of using light. Fibre-optic communication is an example of photonics, as is the technology behind photodetectors and...
29.04.2019 | Event News
17.04.2019 | Event News
15.04.2019 | Event News
18.06.2019 | Life Sciences
18.06.2019 | Life Sciences
18.06.2019 | Life Sciences