And we might not know a thing about them if it weren’t for the little-known artistic experience of Louis Pasteur, says Dr. Gal.
Hands and cue balls
Pasteur was born in 1822 to a French family of modest means. His dad was a soldier in Napoleon’s army and a tanner. As a teenager, Pasteur made portraits of his friends, family and dignitaries. But after his father urged him to pursue a more serious profession — one that would feed him — he became a scientist. At the age of 24 he would discover chirality.
To understand chirality, consider two objects held up before a mirror: a white cue ball from a pool table and your hand. The reflection of the ball is exactly like the original. If you could reach into that mirror, pull out the reflection and cram it inside the original, they’d match up point for point. But if you tried the same thing with your hand, no matter how much you tried, the mirror image would never fit into the original.
At the molecular level some objects are like cue balls, and they are always superimposable. But other things are like hands, and they can never be combined. Hands, like the crystals Pasteur would eventually discover, are chiral. And that discovery all came down to an accident in a vat of wine.
Molecular secrets in a vat of wine
During winemaking, a chemical called tartaric acid builds up on vat walls. In the 18th and 19th centuries, makers of medicine and dyes used this acid.
In 1819, factory workers boiled wine too long and accidentally produced paratartaric acid, which had unique properties that intrigued scientists like Pasteur.
The study of the acid was related to the study of crystal structures, which at the time seemed like a way to help solve the mystery of how molecules were built. Observing the various ways crystals interacted with light gave scientists clues about their properties.
Earlier in the 19th century, Jean-Baptiste Biot, a French physicist, discovered that tartaric acid was optically active. That is, when Biot shined polarized light (which moves out in only one direction, say vertically or horizontally, rather than all directions) through tartaric acid crystals in a solution, they rotated the light clockwise or counterclockwise. But no one knew how the crystals did it.
When studying the paratartaric acid, Pasteur found that it produced two kinds of crystals — one like those found in tartaric acid and another that was the mirror opposite. The crystals were handed, or what the Greeks call chiral (kheir) for hand. And they were not optically active, like the tartaric acid.
Pasteur concluded that the mirror-image crystals, together as a 50/50 mix in the solution, canceled out each other’s ability to rotate polarized light. And without even knowing how a molecule was built, just eight months after receiving his doctorate, he said that their molecular structure was chiral, too. Chemistry changed forever.
“Several famous or much more accomplished scientists, some well along their illustrious careers studied the same molecules, the same substances,” said Dr. Gal. “Realistically you would think they’d have beaten him to the punch, and yet they missed it.”
So why did this young, inexperienced chemist get it right?
Dr. Gal thinks the answer might lie in the artistic passions of Pasteur’s youth. Even as a scientist, Pasteur remained closely connected to art. He taught classes on how chemistry could be used in fine art and attended salons. He even carried around a notebook, jotting down 1-4 ratings of artwork he visited.
And then Dr. Gal stumbled upon a letter Pasteur had written to his parents about a lithographic portrait he had made of a friend.
Lithography back then involved etching a drawing onto a limestone slab with wax or oil and acid, and pressing a white piece of paper on top of it. The resulting picture was transposed, like a mirror image of the drawing left on the slab.
In his letter, Pasteur wrote:
“I think I have not previously produced anything as well drawn and having as good a resemblance. All who have seen it find it striking. But I greatly fear one thing, that is, that on the paper the portrait will not be as good as on the stone; this is what always happens.”
Eureka. “Isn’t this the explanation of how he saw the handedness on the crystals — because he was sensitized to that as an artist?” Dr. Gal proposed.
Mirror, mirror, everywhere
For various reasons, Pasteur eventually turned to biology. Perhaps he recognized that chirality could play a big role in it, some suggest.
We now know that many drugs contain molecules that exist in two chiral forms, and that the two forms can react differently in the body. The most tragic example occurred in the 1950s and ’60s, when doctors prescribed Thalidomide, a drug for morning sickness and other ailments, to pregnant women. The drug also contained a chiral molecule that caused disastrous side effects in many babies.
Today, pharmaceutical companies work harder to separate the active and inactive forms of molecules, and the Food and Drug Administration issued rules to crack down on many chiral drugs in the 1990s. But not all are dangerous, and some were grandfathered in. For example, the pain reliever ibuprofen, as formulated in the United States, contains a 50/50 mix of chiral molecules: one that reduces headaches and its mirror image, which does not appear to be harmful.
“Many objects in our universe have this property of chirality,” said Dr. Gal.
In the mirror, in a vat of wine heated too long, on a piece of limestone and in your body: The non-superimposable hands of the universe were discovered by a man who wanted to be an artist, but settled for science.
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