The Universe and Life is asymmetric: Chirality
By The Astronomist on Friday, January 21, 2011 The shadow of symmetry haunts physics. Symmetry is invoked to understand nature concisely, but broken symmetry is invoked to understand nature completely. Physics is filled with examples of shattered symmetries: there is more matter than antimatter, neutrinos only come in the left handed spin flavor, and quantum processes break symmetries constantly, but nature also violates symmetry in chemistry and biology in a very clever manner. Chemistry and biology are subjects I do no normally touch upon, but I am intrigued by the curious circumstance of life on Earth: many molecules are not superimposable upon their mirror images, a property called chirality, and life on Earth has a preference for these chiral mirror configurations. Physics and life is inherently asymmetric.
That something is not identical to its mirror image is a property known as chirality. Hands (etymologically the word chirality is derived from the Greek word for hand), spiral galaxies, and the DNA helix are all examples of chiral objects. In particle physics chirality is a more abstract notion defined by transformations of a particle with respect to a left right of left handed representation in the Poincaré group. In chemistry chirality is well described by analogy to your hands wherein left and right hands cannot be superposed on each other even though the fingers are the same and match up.
This article is an exploration of chirality in biochemistry. I want to ask what makes life chiral, why is life chiral, and how did life become chiral. In order to supplement my limited knowledge of the subject I interviewed a world expert and author of over twenty papers on the subject, Robert Compton, who I must give a deep thanks to for being willing to answer my silly questions.
It is important to accept that the concept of symmetry is tinted by the human notion of harmonious or aesthetically pleasing forms, but the strict mathematical interpretation of symmetry relies upon metrics of geometry. To this end many seemingly symmetric forms in the living natural world are actually examples of broken symmetries: spiral tree trunks, the human form, and sea shells (which generally only coil in one particular direction according to species). The remarkable thing is that this macro asymmetry can be traced back to a micro asymmetry in the chemistry of life. The arrangement of atoms in a molecule defines the function of that molecule, but even molecules with the same chemical configuration can behave differently as in the case of chiral molecules which are like mirror images of the same molecule that come in 'left' and 'right' handed forms. The great asymmetry of life is that all living organisms on Earth almost exclusively utilize the left handed (or levorotatory) configuration for amino acids and the right handed (or dextrorotatory) configuration for sugars belonging to DNA or RNA.
Perhaps it is trivial or obvious that life is chiral when looking at the nautilus, but this obvious chirality is a macroscopic feature which belies the fine arrangement of atoms which defines the chirality of biomolecules.
Different structural forms of compounds with the same molecular formula are known as isomers to chemists. A stereoisomer is an isomeric molecule which has the identical constitution and sequence of bonded atoms, but has a different three-dimensional geometry in space. An enantiomer is one specific steroisomer of the two possible mirror images that are non-superposable. The dominance of the left handed chiral enantiomer in biology is a massive blow to the idea that nature is perfectly symmetric and is an unsolved mystery as to why nature is this way.
Many molecules are chiral, however because molecules are constantly vibrating the instantaneous structure of a molecule may lack the exact structure or symmetry seen in an ideal model. Regardless, enantiomers have identical chemical properties except when they react with other molecules which are also enantiomeric in which case chiral forces yield a difference in behavior. Further, and perhaps more important for biology, particularly astrobiology, is that enantiomers have identical physical properties except with respect to the way they interact with plane-polarized or circularly polarized light or other chiral compounds. A pure enantiomer compound will rotate the plane of a monochromatic plane-polarized light by a certain angle in one direction, say clockwise, while the other enantiomer form of the compound will rotate the light by an equal amount in the opposite direction. Things that rotate light are said to be optically active. Measurements with a polarimeter allow chemists to determine if a compound is chiral or not. Polarization of light by organic compounds was discovered in 1815 by the French physicist and chemist Jean-Baptiste Biot. He found that organically produced chemical solutions consistently rotated plane polarized light, but laboratory synthesized chemicals did not reproduce the rotation. Beyond conjectures he had no explanation for the phenomena.Years later Louis Pasteur preformed a similar experiment with tartaric acid produced from grapes and tartaric acid synthesized in the lab. Pasteur went further and somehow used tweezers and a microscope (I do not conceive to understand how) to separate the tartaric acid crystals which he produced in the laboratory into piles of left and right handed molecules. He found that polarized light was rotated by the left handed molecules that he had selected in the same way the polarized light was rotated by the organic tartaric acid. He concluded that chiral molecules are responsible for the rotation of polarized light.
cont...
By The Astronomist on Friday, January 21, 2011 The shadow of symmetry haunts physics. Symmetry is invoked to understand nature concisely, but broken symmetry is invoked to understand nature completely. Physics is filled with examples of shattered symmetries: there is more matter than antimatter, neutrinos only come in the left handed spin flavor, and quantum processes break symmetries constantly, but nature also violates symmetry in chemistry and biology in a very clever manner. Chemistry and biology are subjects I do no normally touch upon, but I am intrigued by the curious circumstance of life on Earth: many molecules are not superimposable upon their mirror images, a property called chirality, and life on Earth has a preference for these chiral mirror configurations. Physics and life is inherently asymmetric.
That something is not identical to its mirror image is a property known as chirality. Hands (etymologically the word chirality is derived from the Greek word for hand), spiral galaxies, and the DNA helix are all examples of chiral objects. In particle physics chirality is a more abstract notion defined by transformations of a particle with respect to a left right of left handed representation in the Poincaré group. In chemistry chirality is well described by analogy to your hands wherein left and right hands cannot be superposed on each other even though the fingers are the same and match up.
This article is an exploration of chirality in biochemistry. I want to ask what makes life chiral, why is life chiral, and how did life become chiral. In order to supplement my limited knowledge of the subject I interviewed a world expert and author of over twenty papers on the subject, Robert Compton, who I must give a deep thanks to for being willing to answer my silly questions.
It is important to accept that the concept of symmetry is tinted by the human notion of harmonious or aesthetically pleasing forms, but the strict mathematical interpretation of symmetry relies upon metrics of geometry. To this end many seemingly symmetric forms in the living natural world are actually examples of broken symmetries: spiral tree trunks, the human form, and sea shells (which generally only coil in one particular direction according to species). The remarkable thing is that this macro asymmetry can be traced back to a micro asymmetry in the chemistry of life. The arrangement of atoms in a molecule defines the function of that molecule, but even molecules with the same chemical configuration can behave differently as in the case of chiral molecules which are like mirror images of the same molecule that come in 'left' and 'right' handed forms. The great asymmetry of life is that all living organisms on Earth almost exclusively utilize the left handed (or levorotatory) configuration for amino acids and the right handed (or dextrorotatory) configuration for sugars belonging to DNA or RNA.
Perhaps it is trivial or obvious that life is chiral when looking at the nautilus, but this obvious chirality is a macroscopic feature which belies the fine arrangement of atoms which defines the chirality of biomolecules.
Different structural forms of compounds with the same molecular formula are known as isomers to chemists. A stereoisomer is an isomeric molecule which has the identical constitution and sequence of bonded atoms, but has a different three-dimensional geometry in space. An enantiomer is one specific steroisomer of the two possible mirror images that are non-superposable. The dominance of the left handed chiral enantiomer in biology is a massive blow to the idea that nature is perfectly symmetric and is an unsolved mystery as to why nature is this way.
Many molecules are chiral, however because molecules are constantly vibrating the instantaneous structure of a molecule may lack the exact structure or symmetry seen in an ideal model. Regardless, enantiomers have identical chemical properties except when they react with other molecules which are also enantiomeric in which case chiral forces yield a difference in behavior. Further, and perhaps more important for biology, particularly astrobiology, is that enantiomers have identical physical properties except with respect to the way they interact with plane-polarized or circularly polarized light or other chiral compounds. A pure enantiomer compound will rotate the plane of a monochromatic plane-polarized light by a certain angle in one direction, say clockwise, while the other enantiomer form of the compound will rotate the light by an equal amount in the opposite direction. Things that rotate light are said to be optically active. Measurements with a polarimeter allow chemists to determine if a compound is chiral or not. Polarization of light by organic compounds was discovered in 1815 by the French physicist and chemist Jean-Baptiste Biot. He found that organically produced chemical solutions consistently rotated plane polarized light, but laboratory synthesized chemicals did not reproduce the rotation. Beyond conjectures he had no explanation for the phenomena.Years later Louis Pasteur preformed a similar experiment with tartaric acid produced from grapes and tartaric acid synthesized in the lab. Pasteur went further and somehow used tweezers and a microscope (I do not conceive to understand how) to separate the tartaric acid crystals which he produced in the laboratory into piles of left and right handed molecules. He found that polarized light was rotated by the left handed molecules that he had selected in the same way the polarized light was rotated by the organic tartaric acid. He concluded that chiral molecules are responsible for the rotation of polarized light.cont...
