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Plant enzymes can favor one mirror-image form of a molecule over the other—not because they undergo learning, but because evolutionary changes make one form react more efficiently. A study of borneol dehydrogenases traced that preference to a combination of mutations, including changes far from the enzyme’s active site.
What are mirror-image molecules?
Some molecules come in two forms that are mirror images of each other but cannot be superimposed, much like a left hand and a right hand. These are called enantiomers. Although their atoms are connected in the same order, their three-dimensional arrangements differ.
That distinction matters in chemistry and biology: a molecule’s shape affects how it fits and reacts with other molecules. Borneol and its mirror-image form, isoborneol, are an example relevant to plant borneol dehydrogenases.
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How can an enzyme distinguish between enantiomers?
An enzyme is a protein that speeds up a chemical reaction. Its active site—the region where a reacting molecule binds—can favor a particular three-dimensional fit. But the enzyme is not a rigid lock. Its structure moves, and regions beyond the active site can influence how a bound molecule is positioned and how long it stays in a state that allows the reaction to proceed.
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Borneol dehydrogenases catalyze the conversion of borneol into camphor. The study examined why plant versions of these enzymes react more selectively with one borneol form than with its mirror image.
How did researchers trace the change over evolutionary time?
Researchers from Freie Universität Berlin, Graz University of Technology, and Georgia Institute of Technology used ancestral sequence reconstruction. They started with a family tree built from 97 plant sequences, computationally inferred sequences for ancestral enzymes, produced those proteins in the laboratory, and compared their behavior. The approach tests plausible reconstructed ancestors; it does not observe evolution happening directly.
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In the university’s October 1, 2026 summary, the researchers compared an older, unselective enzyme called N30 with the younger, highly selective N32. Freie Universität Berlin reports that:
- N30 and N32 differed by 19 amino-acid mutations.
- Only one of the 19 changes was in the active site.
- Introducing that active-site mutation into the unselective ancestor doubled its selectivity.
- Reversing the mutation in the selective ancestor removed its preference.
- The active-site mutation alone did not produce high selectivity; three additional changes elsewhere in the enzyme had to be combined with it.
Did one mutation make the enzyme selective?
No. The active-site mutation had a measurable effect, but it was not enough for high selectivity. In the reconstructed enzymes, the strong preference emerged from that mutation working together with three further changes outside the active site. The result points to an evolutionary process involving a network of changes, rather than a single decisive switch.
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Why do mutations far from the active site matter?
The university summary reports no obvious structural differences that explained the enzymes’ preferences. Instead, computational simulations indicated that the better-reacting borneol form stayed in a catalytically productive position for longer. The other form was held less tightly and was more exposed to surrounding water.
This is the authors’ simulation-supported explanation of how the mutations may affect reaction dynamics, not a direct observation of every molecular event. Their interpretation is that multiple small changes—including changes away from the reaction center—alter the enzyme’s motion and the behavior of the molecule it binds.
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How does this compare with another plant-enzyme example?
A separate 2013 study of thyme enzymes offers a different route to stereochemical divergence. The related sabinene hydrate synthases TPS6 and TPS7 produced opposing enantiomers among similar product spectra. In that case, stereospecificity was traced to the formation of the first intermediate, and one amino-acid position had a major effect.
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The contrast is useful, but the findings are not interchangeable: the thyme work concerned product stereochemistry and a major-effect position, while the borneol dehydrogenase study used reconstructed ancestors to investigate substrate enantioselectivity and found that high selectivity depended on a combination of mutations.
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Could this help make medicines or fragrances?
Potentially. Freie Universität Berlin describes borneol and isoborneol as obtainable as a mixture from α-pinene, an inexpensive bio-based raw material. More selective enzymes could, in principle, help produce or separate individual forms for pharmaceutical, cosmetic, or fragrance applications.
Those are prospective uses, not evidence of a commercial process or industrial deployment. The study’s broader design implication is that enzyme engineering may need to consider mutations throughout a protein, not only changes at the active site.
What the study establishes—and what it does not
The study offers an evolutionary explanation for how selectivity developed in this particular plant enzyme family: reconstructed ancestors and mutation experiments link high selectivity to several changes, while simulations suggest a dynamic explanation for their effect. It is not a universal account of how all enzymes distinguish enantiomers. Enzyme families can reach stereochemical outcomes through different reactions and molecular mechanisms.
Freie Universität Berlin’s October 1, 2026 summary quotes study coauthor and Freie Universität Berlin researcher Dr. Bernhard Loll: “We were able to demonstrate how the different reaction to the two different borneol forms developed over the course of the enzymes’ evolution. What was crucial here was not major structural changes to the enzyme, but the interplay of many small changes that influenced the dynamics of the enzyme and bound molecule. This provides us with important indications of how enzymes could be specifically engineered for biotechnological applications in the future.”
The study is titled “Deciphering the Evolutionary Origin of the Enantioselectivity of Short-Chain Dehydrogenases from Plants Toward 1-Borneol.” The detailed facts above are based on the university’s institutional summary; the summary does not establish additional selectivity ratios or measurements beyond those stated here.
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