Chemists produce all eight possible types of polypropylene building blocks from one starting material.

Credit: Applied Chemistry International Edition (2023). DOI: 10.1002/anie.202317525

To synthesize potential drugs or natural products, you need natural substances in specific mirror image forms and with high purity. For the first time, chemists at the University of Bonn have succeeded in producing all eight possible types of polypropionate building blocks from a single starting material in a relatively simple process. Their work I am now published. Applied Chemistry International Edition.

Polypropionates are. Which can help save lives. They are needed to make reserve antibiotics, compounds that are only used to treat infections caused by drug-resistant bacteria. In nature, chiral compounds exist in two different forms that share the same molecular formula but are of each other, like right and left hands. Chemists call this “chirality”, which literally means “handedness”.

“Interestingly, the mirror shapes can have very different properties,” explains Professor Andreas Gansoer of the Kekulé Institute of Organic Chemistry and Biochemistry at the University of Bonn. “A well-known example is undoubtedly carvone. The dextro-, or ‘right-handed,’ form of this molecule gives caraway its aroma, while its levo-, or ‘left-handed,’ form is what gives peppermint its distinctive smell. Gives.”

Many drugs also contain molecules that have different conformational properties. “Different properties also produce different effects within. so it is important to use the right form in medicine,” says Gansauer, who is also a member of the Mater transdisciplinary research area at the University of Bonn.

“Although polypropionates occur naturally, we need them with a high degree of selectivity—that is, within a specific species—and with a high level of purity to use them in drug development,” he prob. Pointing out further. “Until now, however, the process of making synthetic polypropionate has been complicated and time-consuming.”

Turning one into eight

The Kekulé Institute for Organic Chemistry and Biochemistry team: (from left) Katharina Pieper, Prof. Dr. Andreas Gansäuer, Christian Köhler and Regine Mika from the Kekulé Institute for Organic Chemistry and Biochemistry at the University of Bonn. Credit: Volker Lannert / Universität Bonn

He and his team have now come up with a method that can easily produce the desired variety. “We are able to make eight different varieties from the same starting material, in this case an alcohol,” reveals Gansäuer. Polypropionates are. Composed of hydrocarbon chains with an alternating arrangement of methyl and hydroxyl groups. “Different alternatives associated with all three On the chains we get a total of eight different conformations that we call isomers of our polypropionate building blocks.”

Researchers at the University of Bonn used two known methods to make the first four precursors of the eight isomers and added a new one, called hydrosilylation. “The isomers are made by us by adding fluoride for the dextro form or titanium for the levo form,” says Gansauer.

This process is like branches growing on a tree. It all starts at the trunk, in this case the wine, from which the two branches first diverge. This produces an epoxide—a three-membered ring structure containing an oxygen atom—in mirror image variants. These first two to two more branches are formed by adding an olefin, a carbon-carbon double bond to each. In the final step, known as hydrosilylation of epoxides, a total of eight branches are separated from these four.

The technique has several advantages. “Our method works at room temperature,” says Gansäuer. “Some classical reactions have to be carried out at very low temperatures. Also, we don’t need to use precious metals as catalysts, which means our method is more sustainable.”

“Our work can be used as a basis for drug synthesis. When you’re developing drugs, you never know in advance what kind of substance you’ll need. “If you can make eight different shapes, like the one shown here, you can make other interesting materials you want, so you’re more likely to get an efficient structure,” says Gansauer. are

More information:
Katharina Pieper et al, A Flexible Synthesis of Polypropionates via Diastereodivergent Reductive Ring-Opening of Trisubstituted Secondary Glycidols, Applied Chemistry International Edition (2023). DOI: 10.1002/anie.202317525

Provided by
University of Bonn

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