Homochirality is a uniformity of chirality, or handedness. Objects are chiral when they cannot be superposed on their mirror images. For example, the left and right hands of a human are approximately mirror images of each other but are not their own mirror images, so they are chiral. In chemistry, chirality is a geometric property of some compounds and ions. These compounds exist in two different chiral conformations, enantiomers, often described as the left-handed and right-handed isomers of a compound (denoted by L- (levorotatory to the left) and D- (dextrorotatory to the right), respectively, from how chiral molecules rotate plane-polarized light). The term homochiral is used to describe enantiopure samples of substances in which all the constituents are the same enantiomer. Enantiomers have the same chemical properties in an achiral environment, so abiotic chemical processes typically produce racemic mixtures of chiral compounds, i.e., mixtures containing equal amounts of L- and D-isomers. However, many biologically-synthesized compounds are homochiral. For example, 19 of the 20 genetically-coded proteinogenic amino acids are left-handed, with exception of the achiral glycine, and biological sugars are right-handed. Many theories have been proposed for the "function" of homochirality in nature: it may be a form of information storage and may reduce entropy barriers in the formation of large organized molecules. It has been experimentally verified that amino acids form large aggregates in larger abundance from enantiopure samples than from racemic ones. Enantiomeric impurities also impede RNA replication and chain elongation, processes central to both modern cellular processes like transcription and the RNA world hypothesis. As homochirality is ubiquitous in extant biology, a key question in origins of life and prebiotic chemistry research is how biological homochirality could have arisen from racemic mixtures of the simple chemical building blocks of life. Many mechanisms for the origin of homochirality have been proposed. Some of these models propose three distinct steps: a mirror-symmetry breaking mechanism to create a minute enantiomeric imbalance (enantiomeric excess or ee) from a racemic mixture, subsequent chiral amplification to achieve a larger ee or full homochirality (i.e., ee=100%), and finally chiral transmission/propagation to transfer chirality from one set of molecules to another. In addition, another important consideration is the environmental plausibility of proposed mechanisms — whether a symmetry breaking, amplification, or propagation process could occur over relevant timescales and using only materials that could feasibly be available prebiotically under early Earth conditions.
History of the term Homochirality was introduced by Lord Kelvin in 1904, the year that he published his Baltimore Lecture of 1884. Kelvin used homochirality as a relationship between two molecules, i.e. two molecules are homochiral if they have the same chirality. Homochiral has been used in the same sense as enantiomerically pure. This is permitted in some journals (but not encouraged), its meaning in these journals being the preference of a process or system for a single optical isomer of a pair.
In biology Homochirality is a common characteristic of biological compounds, including the building blocks of macromolecules like nucleic acids and proteins. Amino acids, the building blocks of peptides and enzymes, appear almost exclusively in their left-handed form and all D-amino acids found in protein sequences are a result of post-translational modifications of the original L-amino acid. Ribose and deoxyribose, the sugar components of RNA and DNA nucleotide monomers, meanwhile, are all right-handed. Other cellular metabolites are also homochiral; for example, malate and isocitrate, two intermediates in the citric acid cycle, are homochiral in their L- and D- forms, respectively. In modern biology, enzymatic activity is what imposes homochirality on these metabolites and others, including hormones, toxins, fragrances and food flavors. Biological organisms easily discriminate between molecules with different chiralities. This can affect physiological reactions such as smell and taste. Carvone, a terpenoid found in essential oils, smells like mint in its L-form and caraway in its R-form. Limonene tastes like citrus when right-handed and pine when left-handed. Homochirality also affects the response to drugs. Thalidomide, in its left-handed form, cures morning sickness; in its right-handed form, it causes birth defects. Unfortunately, even if a pure left-handed version is administered, some of it can convert to the right-handed form in the patient. Many drugs are available as both a racemic mixture and an enantiopure drug . Depending on the manufacturing process, enantiopure forms can be more expensive to produce than stereochemical mixtures. Chiral preferences can also be found at a macroscopic level. Snail shells can be right-turning or left-turning helices, but one form or the other is strongly preferred in a given species. In the edible snail Helix pomatia, only one out of 20,000 is left-helical. The coiling of plants can have a preferred chirality and even the chewing motion of cows has a 10% excess in one direction.
Origins of biomolecular homochirality
Symmetry breaking Theories for the origin of homochirality in the molecules of life can be classified as deterministic or based on chance depending on their proposed mechanism. If there is a relationship between cause and effect – that is, a specific chiral field or influence causing the mirror symmetry breaking – the theory is classified as deterministic; otherwise it is classified as a theory based on chance (in the sense of randomness) mechanisms.
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