Anders Grundtvig Utzon DTU Kemi

Student gets Novo scholarship to develop asymmetric synthesis

Friday 11 Dec 20
by Tine Naja Berg

About the thesis

Title: New chemoenzymatic tools: Highly valuable chemical entities

Supervisor: Assistant Professor, Katrine Qvortrup

The aim is to develop a short and efficient chemoenzymatic method for the synthesis of optically pure beta-stereogenic primary alcohols. These alcohols can i.a. used in the manufacture of e.g ibuprofen, naproxen, naproxol, vitamins E, K and bongkrekic acids.

The chemical methods that will be developed will provide access to a wide range of biologically interesting but synthetically challenging compounds, which with the new method and knowledge should be easier to produce in the future and ultimately contribute to cheaper medicines.

About the Novo Scholarship Program

The Novo Scholarship Program is the Novo Nordisk Foundation's annual scholarship for thesis writing. Behind the scholarship is Novozymes together with Novo Nordisk, and it is awarded to some of the most talented students who write a thesis within Novo Nordisk's and Novozymes' research areas.

Chemistry student Anders Grundtvig Utzon receives the Novo scholarship for his thesis, where he will develop a new method within asymmetric synthesis, which is used in the production of optically pure chiral substances for e.g. medicines.

Chiral substances are increasingly being used. They are used i.a. in the pharmaceutical industry for the development of new medicines, but they are also used in agriculture e.g pesticides and in the food industry, and the market for chiral technologies is expected to reach $ 7.6 billion in 2022 worldwide.

That a substance is chiral means that it can exist as two molecules with exactly the same basic structure, which are mirror-images of each other - just like our hands. The molecules are thus not identical but are simply made up of the same set of atoms in relation to each other, and because their relative structure is similar, it is difficult to control which mirror-image is formed in a chemical reaction.

However, it is crucial to be able to control this process when the substance is to be used in new medicine, as the two mirror-image molecules do not necessarily have the same effect on the body. Therefore, in a simplified way, you will only get hold of one active mirror-image molecule, which is called an optically pure substance, and that is precisely the focus in Anders Grundtvig Utzon's master thesis.

“I want to develop a new method to produce only optically pure substances - more specifically the one mirror-image molecule of so-called beta-stereogenic primary alcohols. If we can control this process in a way that it can be scaled up, it will have a big impact on how cheaply we can produce chemical building blocks for the manufacture of medicines, and the world needs cheap medicine. Today, it is still common to "sort" the unwanted mirror image molecules in the production process, and it is, of course, an expensive method ", explains Anders, who studies Applied Chemistry at DTU.

He is one of the talented students who has been selected to receive the Novo Nordisk Foundation's grant of a total of DKK 42,000 for his master thesis, and he has just completed his initial experiments and is now ready to start the thesis.

"I am very honoured by the recognition of receiving this Novo scholarship. I am very passionate about studying chemistry, and therefore it is extremely nice to know that others also think that what I want to investigate has potential”, says Anders.

Mirror-image molecules work differently
However, it is not quite simple to deal with chiral substances. In nature, there is typically only a single of the two mirror-image forms of the same substance in biological material, and this must also be ensured when dealing with synthetic compounds. Two different mirror-image forms of a substance do not necessarily have the same biological effect.

Anders explains:

“There are many examples of chiral substances where the two mirror-images have different effects. Chiral fragrances are especially known for the fact that their two mirror-images smell different. The effect may also be different in medicines. For example, the drug Darvon, which has an analgesic effect, whereas its mirror-image, the drug Novrad, is antitussive. However, the difference between a chiral medicine's two mirror-images can be much more marked and in the worst case, one mirror-image can potentially save lives, while another can cause serious side effects”.

However, there is still a need for more knowledge and more efficient methods of producing the substances, and therefore it is a topic that researchers in the field of chemistry are still studying at an international level.

“My thesis is very interdisciplinary in the chemical world both theoretically and methodologically. It, therefore, places great demands on my knowledge in many areas within the chemical subject area, but that is exactly what drives me, and I am therefore very much looking forward to getting started”, concludes Anders.

Chirality in chemistry

Chiral molecules exist as mirror-images, but are otherwise made up of exactly the same chemical groups. The word chiral comes from "cheiros", which means hand in Greek. The molecules are thus as different as the right and left hand - they are each other's mirror-images.

It was the French chemist and microbiologist Louis Pasteur who, in the mid-19th century, discovered the phenomenon of chirality during experiments in which he converted ordinary tartaric acid into grape acid. He found that tartaric acid differs from tartaric acid in that a solution of tartaric acid cannot rotate the plane of polarization of polarized light, which a solution of tartaric acid can. Based on his discoveries, chiral compounds are classified according to which path they rotate plane-polarized light. Connections that turn the light to the left are given the designation (-), while connections that turn the light to the right are given the designation (+).

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