Chemists Unlock Eight Polypropionate Variants from One Source

Polypropionates are natural products that can help save lives. They are needed to make reserve antibiotics, compounds that are only ever used to treat infections caused by drug-resistant bacteria. However, synthesizing polypropionates in a specific variant and with a high degree of purity has been a challenge for chemists. Now, researchers from the University of Bonn have found a solution. They have developed a method that allows them to produce all eight possible variants of polypropionate building blocks from a single starting material in a relatively straightforward process. Their work has been published in Angewandte Chemie International Edition.

Polypropionates are chemical compounds consisting of hydrocarbon chains with an alternating sequence of methyl and hydroxyl groups. The different substituents attached to the three carbon atoms on the chains give rise to eight different forms that are called isomers. These isomers can have very different properties and effects, so it is important to use the right one in drug manufacture. For example, one isomer of erythromycin, a widely used antibiotic, is 100 times more potent than another.

The researchers from the University of Bonn used two known methods for creating the first four precursors to the eight isomers and added a new one, known as hydrosilylation: “The isomers are produced by us adding either fluoride for the dextro-form or titanium for the levo-form,” explains Professor Andreas Gansäuer from the Kekulé Institute of Organic Chemistry and Biochemistry at the University of Bonn. “The process is similar to how branches form on a tree.”

The advantage of this method is that it allows the chemists to produce all eight variants from a single starting material, an alcohol in this case, without having to change the reaction conditions or use complex purification steps. The method also works with different alcohols, which means that it can be used to create a variety of polypropionate building blocks.

The researchers hope that their method will facilitate the synthesis of new drugs and natural products based on polypropionates. “We have shown that it is possible to produce all eight variants of polypropionate building blocks from one source in a simple and efficient way,” says Gansäuer. “This opens up new possibilities for discovering and developing new compounds with potential applications in medicine and biotechnology.”

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