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Two enantiomers of a generic amino acid that is chiral

Chirality /kaɪˈrælɪtiː/ is a property of asymmetry important in several branches of science. The word chirality is derived from the Greek, χειρ (kheir), "hand", a familiar chiral object.

An object or a system is chiral if it is distinguishable from its mirror image; that is, it cannot be superposed onto it. Conversely, a mirror image of an achiral object, such as a sphere, cannot be distinguished from the object. A chiral object and its mirror image are called enantiomorphs (Greek opposite forms) or, when referring to molecules, enantiomers. A non-chiral object is called achiral (sometimes also amphichiral) and can be superposed on its mirror image.

The term was first used by Lord Kelvin in 1893 in the second Robert Boyle Lecture at the Oxford University Junior Scientific Club which was published in 1894:

I call any geometrical figure, or group of points, 'chiral', and say that it has chirality if its image in a plane mirror, ideally realized, cannot be brought to coincide with itself.^[1]

Human hands are perhaps the most universally recognized example of chirality: The left hand is a non-superimposable mirror image of the right hand; no matter how the two hands are oriented, it is impossible for all the major features of both hands to coincide across all axes.^[2] This difference in symmetry becomes obvious if someone attempts to shake the right hand of a person using their left hand, or if a left-handed glove is placed on a right hand. In mathematics chirality is the property of a figure that is not identical to its mirror image.

Mathematics

An achiral 3D object without central symmetry or a plane of symmetry

A table of all prime knots with seven crossings or fewer (not including mirror images).

In mathematics, a figure is chiral (and said to have chirality) if it cannot be mapped to its mirror image by rotations and translations alone. For example, a right shoe is different from a left shoe, and clockwise is different from anti-clockwise.

A chiral object and its mirror image are said to be enantiomorphs. The word enantiomorph stems from the Greek ἐναντίος (enantios) 'opposite' + μορφή (morphe) 'form'. A non-chiral figure is called achiral or amphichiral.

The helix (and by extension a spun string, a screw, a propeller, etc.) and Möbius strip are chiral two-dimensional objects in three-dimensional ambient space. The J, L, S and Z-shaped tetrominoes of the popular video game Tetris also exhibit chirality, but only in a two-dimensional space.

Many other familiar objects exhibit the same chiral symmetry of the human body, such as gloves, glasses (where two lenses differ in prescription), and shoes. A similar notion of chirality is considered in knot theory, as explained below.

Some chiral three-dimensional objects, such as the helix, can be assigned a right or left handedness, according to the right-hand rule.

Geometry

In geometry a figure is achiral if and only if its symmetry group contains at least one orientation-reversing isometry. In two dimensions, every figure that possesses an axis of symmetry is achiral, and it can be shown that every bounded achiral figure must have an axis of symmetry. In three dimensions, every figure that possesses a plane of symmetry or a center of symmetry is achiral. There are, however, achiral figures lacking both plane and center of symmetry. In terms of point groups, all chiral figures lack an improper axis of rotation (S_n). This means that they cannot contain a center of inversion (i) or a mirror plane (σ). Only figures with a point group designation of C₁, C_n, D_n, T, O, or I can be chiral.

Knot theory

A knot is called achiral if it can be continuously deformed into its mirror image, otherwise it is called chiral. For example the unknot and the figure-eight knot are achiral, whereas the trefoil knot is chiral.

Physics

Animation of left-handed (anti-clockwise), circularly polarized, light as viewed in the direction of the source, in agreement with physics and astronomy conventions.

In physics, chirality may be found in the spin of a particle, which may be used to define a handedness (aka chirality) for that particle. A symmetry transformation between the two is called parity. Invariance under parity by a Dirac fermion is called chiral symmetry.

Electro-magnetism

Electromagnetic wave propagation as handedness is wave polarization and described in terms of helicity (occurs as a helix). Polarization of an electromagnetic wave, is the property that describes the orientation, i.e., the time-varying, direction (vector), and amplitude of the electric field vector. For a depiction, see the image to the right.

Chemistry

(S)-Alanine (left) and (R)-alanine (right) in zwitterionic form at neutral pH

A chiral molecule is a type of molecule that has a non-superposable mirror image. The feature that is most often the cause of chirality in molecules is the presence of an asymmetric carbon atom.^[3]^[4]

The term chiral in general is used to describe an object that is non-superposable on its mirror image.^[5]

In chemistry, chirality usually refers to molecules. Two mirror images of a chiral molecule are called enantiomers or optical isomers. Pairs of enantiomers are often designated as "right-" and "left-handed."

Molecular chirality is of interest because of its application to stereochemistry in inorganic chemistry, organic chemistry, physical chemistry, biochemistry, and supramolecular chemistry.

Biology

Shells of two different species of sea snail: on the left is the normally sinistral (left-handed) shell of Neptunea angulata, on the right is the normally dextral (right-handed) shell of Neptunea despecta

In anatomy, chirality is found in the imperfect mirror-image symmetry of many kinds of animal bodies. Organisms such as gastropods exhibit chirality in their coiled shells, resulting in an asymmetrical appearance. Over 90% of gastropod species ^[6] have dextral (right-handed) shells in their coiling, but a small minority of species and genera are virtually always sinistral (left-handed). A very few species (for example Amphidromus perversus^[7]) show an equal mixture of dextral and sinistral individuals.

In humans, chirality (also referred to as handedness or laterality) is an attribute of humans defined by their unequal distribution of fine motor skill between the left and right hands. An individual who is more dexterous with the right hand is called right-handed, and one who is more skilled with the left is said to be left-handed. Chirality is also seen in the study of facial asymmetry.

In flatfish, the Summer flounder or fluke are left-eyed, while halibut are right-eyed.

References

^ Sir William Thomson Lord Kelvin (1894). "The Molecular Tactics of a Crystal". Clarendon Press.
^ Georges Henry Wagnière, On Chirality and the Universal Asymmetry: Reflections on Image and Mirror Image (2007).
^ Organic Chemistry (4th Edition) Paula Y. Bruice.
^ Organic Chemistry (3rd Edition) Marye Anne Fox ,James K. Whitesell.
^ IUPAC, Compendium of Chemical Terminology, 2nd ed. (the "Gold Book") (1997). Online corrected version: (2006–) "chirality".
^ Schilthuizen, M.; Davison, A. (2005). "The convoluted evolution of snail chirality". Naturwissenschaften 92 (11): 504–515. doi:10.1007/s00114-005-0045-2.
^ Amphidromus perversus (Linnaeus, 1758)

External links

English Journal

Direct enantiomeric analysis of Mentha essential oils.

Barba C, Santa-María G, Herraiz M, Martínez RM.SourceInstituto de Ciencia y Tecnología de Alimentos y Nutrición, Consejo Superior de Investigaciones Científicas (ICTAN-CSIC), c/Juan de la Cierva 3, 28006 Madrid, Spain.
Food chemistry.Food Chem.2013 Nov 1;141(1):542-7. doi: 10.1016/j.foodchem.2013.03.013. Epub 2013 Mar 14.
A rapid and fully automated screening of chiral compounds in essential oils, aimed to the selection of natural sources of pure enantiomers of limonene and carvone, is performed by using on-line coupled reversed phase liquid chromatography with gas chromatography and mass spectrometry (RPLC-GC-MS). E
PMID 23768391

Enantioselective separation and transformation of metalaxyl and its major metabolite metalaxyl acid in tomato and cucumber.

Li Y, Dong F, Liu X, Xu J, Chen X, Han Y, Cheng Y, Jian Q, Zheng Y.SourceState Key Laboratory for Biology of Plant Diseases and Insect Pests, Institute of Plant Protection, Chinese Academy of Agricultural Sciences, Beijing 100193, China.
Food chemistry.Food Chem.2013 Nov 1;141(1):10-7. doi: 10.1016/j.foodchem.2013.02.126. Epub 2013 Mar 14.
Many studies have shown the enantioselective transformation of metalaxyl in soil and animals, but little is known about the enantioselective biotransformation of metalaxyl in plants. In this study, a sensitive and convenient chiral liquid chromatography-tandem mass spectrometry method was developed
PMID 23768319

Discrimination of enantiomers based on LSPR biosensors fabricated with weak enantioselective and nonselective receptors.

Guo L, Wang D, Xu Y, Qiu B, Lin Z, Dai H, Yang HH, Chen G.SourceMinistry of Education Key Laboratory of Analysis and Detection Technology for Food Safety (Fuzhou University), Fujian Provincial Key Laboratory of Analysis and Detection Technology for Food Safety, Department of Chemistry, Fuzhou University, Fuzhou 350108, China. Electronic address: guolh@fzu.edu.cn.
Biosensors & bioelectronics.Biosens Bioelectron.2013 Sep 15;47:199-205. doi: 10.1016/j.bios.2013.03.009. Epub 2013 Mar 21.
Chiral recognition based on enantioselective sensors is superior to conventional chromatographic enantioseparation techniques in terms of simplicity and rapidity. Normally, highly specific enantioselective receptors are used for the fabrication of enantioselective sensors. However, to date there onl
PMID 23578974

Japanese Journal

Memory functions of magnetic skyrmions

Koshibae Wataru,Kaneko Yoshio,Iwasaki Junichi,Kawasaki Masashi,Tokura Yoshinori,Nagaosa Naoto
Jpn. J. Appl. Phys. 54(5), 053001, 2015-04-02
… We study, by microsimulation on the chiral magnets, the elementary functions of magnetic skyrmions and the design principles of skyrmionic memory devices. …
NAID 150000110637

Asymmetric transmission of linearly and circularly polarized waves in metamaterial due to symmetry-breaking

Liu De-jun,Xiao Zhong-yin,Ma Xiao-long,Wang Zi-hua
Appl. Phys. Express 8(5), 052001, 2015-04-02
… A two-dimensional chiral structure with an h-shape and H-shape on opposing sides of a dielectric layer is proposed that can realize simultaneously dual-band asymmetric transmission of linearly and circularly polarized waves in the near-infrared band. …
NAID 150000110574

Novel Lifshitz point for chiral transition in the magnetic field

Tatsumi Toshitaka,Nishiyama Kazuya,Karasawa Shintaro
Physics Letters B 743, 66-70, 2015-04
… Based on the generalized Ginzburg–Landau theory, chiral phase transition is discussed in the presence of magnetic field. … Considering the chiral density wave we show that chiral anomaly gives rise to an inhomogeneous chiral phase for nonzero quark-number chemical potential. …
NAID 120005575268