AI Article Synopsis
- Molecular shape is crucial for understanding both biological functions and material properties, and chemists have created specific terms to describe these shapes.
- Noncanonical atropisomers are a unique type of shape-defined molecules that can only be interconverted through complex multibond movements, setting them apart from regular atropisomers and topoisomers.
- Researchers successfully synthesized the peptidic alkaloid tryptorubin A as one of two noncanonical atropisomers and developed a targeted synthetic approach for producing a specific noncanonical small molecule.
Article Abstract
Molecular shape defines function in both biological and material settings, and chemists have developed an ever-increasing vernacular to describe these shapes. Noncanonical atropisomers-shape-defined molecules that are formally topologically trivial but are interconvertible only by complex, nonphysical multibond torsions-form a unique subset of atropisomers that differ from both canonical atropisomers (e.g., binaphthyls) and topoisomers (i.e., molecules that have identical connectivity but nonidentical molecular graphs). Small molecules, in contrast to biomacromolecules, are not expected to exhibit such ambiguous shapes. Using total synthesis, we found that the peptidic alkaloid tryptorubin A can be one of two noncanonical atropisomers. We then devised a synthetic strategy that drives the atropospecific synthesis of a noncanonical atrop-defined small molecule.
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| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC6996792 | PMC |
| http://dx.doi.org/10.1126/science.aay9981 | DOI Listing |
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