Chemists synthesize plant-derived molecules that hold potential as pharmaceuticals

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The article discusses how MIT chemists have developed a new method to synthesize complex molecules called oligocyclotryptamines, originally found in plants. These molecules have potential as antibiotics, analgesics, or cancer drugs. The traditional method of synthesizing these compounds in the lab has been challenging due to small quantities available naturally. The new method developed by the MIT team allows for precise assembly of rings and control of the 3D orientation of components. This approach not only enables scientists to synthesize these plant-derived molecules but also potentially generate new variants with improved medicinal properties or molecular probes to uncover their mechanisms.

The oligocyclotryptamines were originally isolated from Psychotria leaves in New Caledonia. Credit: Jose-Luis Olivares, MIT; molecule provided by Scott et al.

MIT chemists have developed a new way to synthesize complex molecules that were originally isolated from plants and could hold potential as antibiotics, analgesics, or cancer drugs.

These compounds, known as oligocyclotryptamines, consist of multiple tricyclic substructures called cyclotryptamine, fused together by carbon–. Only small quantities of these compounds are naturally available, and synthesizing them in the lab has proven difficult. The MIT team came up with a way to add tryptamine-derived components to a molecule one at a time, in a way that allows the researchers to precisely assemble the rings and control the 3D orientation of each component as well as the final product.

“For many of these compounds, there hasn’t been enough material to do a thorough review of their potential. I’m hopeful that having access to these compounds in a reliable way will enable us to do further studies,” says Mohammad Movassaghi, an MIT professor of chemistry and the senior author of the new study.

In addition to allowing scientists to synthesize oligocyclotryptamines found in plants, this approach could also be used to generate new variants that may have even better medicinal properties, or molecular probes that can help to reveal their mechanism

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