stereochemistry Stereochemistry, a subdiscipline of chemistry, studies the spatial arrangement of atoms that form the structure of molecules and their manipulation. The study of stereochemistry focuses on the relationships between stereoisomers, which are defined ...

, prochiral molecules are those that can be converted from achiral to

chiral Chirality () is a property of asymmetry important in several branches of science. The word ''chirality'' is derived from the Greek language, Greek (''kheir''), "hand", a familiar chiral object. An object or a system is ''chiral'' if it is dist ...

in a single step, such as changing one atom. An achiral species which can be converted to a chiral in two steps is called proprochiral. A molecule having only one plane of symmetry, or an

inversion point In geometry, a point reflection (also called a point inversion or central inversion) is a geometric transformation of affine space in which every point is reflected across a designated inversion center, which remains fixed. In Euclidean or ...

and no plane of symmetry, is prochiral if it is possible to change one of the two sides or to destroy the symmetry in another way. But a molecule with more symmetry, such as

ethane Ethane ( , ) is a naturally occurring Organic compound, organic chemical compound with chemical formula . At standard temperature and pressure, ethane is a colorless, odorless gas. Like many hydrocarbons, ethane is List of purification methods ...

, may require two substitutions to become chiral, and is thus proprochiral.

Methane Methane ( , ) is a chemical compound with the chemical formula (one carbon atom bonded to four hydrogen atoms). It is a group-14 hydride, the simplest alkane, and the main constituent of natural gas. The abundance of methane on Earth makes ...

requires three substitutions to become chiral. If two identical

substituent In organic chemistry, a substituent is one or a group of atoms that replaces (one or more) atoms, thereby becoming a moiety in the resultant (new) molecule. The suffix ''-yl'' is used when naming organic compounds that contain a single bond r ...

s are attached to an sp³-hybridized

atom Atoms are the basic particles of the chemical elements. An atom consists of a atomic nucleus, nucleus of protons and generally neutrons, surrounded by an electromagnetically bound swarm of electrons. The chemical elements are distinguished fr ...

, the descriptors ''pro''-R and ''pro''-S are used to distinguish between the two. Promoting the ''pro''-R substituent to higher priority than the other identical substituent results in an ''R'' chirality center at the original sp³-hybridized atom, and analogously for the ''pro''-S substituent. A

trigonal planar In chemistry, trigonal planar is a molecular geometry model with one atom at the center and three atoms at the corners of an equilateral triangle, called peripheral atoms, all in one plane. In an ideal trigonal planar species, all three ligands a ...

sp²-hybridized atom can be converted to a chiral center when a substituent is added to the ''re'' or ''si'' () face of the molecule. A face is labeled ''re'' if, when looking at that face, the substituents at the trigonal atom are arranged in increasing Cahn-Ingold-Prelog priority order (1 to 2 to 3) in a clockwise order, and ''si'' if the priorities increase in anti-clockwise order; note that the designation of the resulting chiral center as ''S'' or ''R'' depends on the priority of the incoming group. The concept of prochirality is necessary for understanding some aspects of enzyme

stereospecificity In chemistry, stereospecificity is the property of a reaction mechanism that leads to different stereoisomeric reaction products from different stereoisomeric reactants, or which operates on only one (or a subset) of the stereoisomers."Overlap C ...

. Alexander Ogston pointed out that when a symmetrical molecule is placed in an asymmetric environment, such as the surface of an

enzyme An enzyme () is a protein that acts as a biological catalyst by accelerating chemical reactions. The molecules upon which enzymes may act are called substrate (chemistry), substrates, and the enzyme converts the substrates into different mol ...

, supposedly identically placed groups become distinguishable. In this way he showed that earlier exclusion of non-chiral

citrate Citric acid is an organic compound with the formula . It is a colorless weak organic acid. It occurs naturally in citrus fruits. In biochemistry Biochemistry, or biological chemistry, is the study of chemical processes within and relati ...

as a possible intermediate in the tricarboxylate cycle was mistaken. Another biochemical example of prochirality is

glycerol Glycerol () is a simple triol compound. It is a colorless, odorless, sweet-tasting, viscous liquid. The glycerol backbone is found in lipids known as glycerides. It is also widely used as a sweetener in the food industry and as a humectant in pha ...

. It is achiral, but when it is

phosphorylated In biochemistry, phosphorylation is described as the "transfer of a phosphate group" from a donor to an acceptor. A common phosphorylating agent (phosphate donor) is ATP and a common family of acceptor are alcohols: : This equation can be writt ...

(at carbon number 3 in

stereospecific numbering Glycerophospholipids or phosphoglycerides are glycerol-based phospholipids. They are the main component of biological membranes in eukaryotic cells. They are a type of lipid, of which its composition affects membrane structure and properties. Tw ...

) the molecule becomes the chiral

glycerol 3-phosphate ''sn''-Glycerol 3-phosphate is the organic ion with the formula HOCH2CH(OH)CH2OPO32-. It is one of two stereoisomers of the ester of dibasic phosphoric acid (HOPO32-) and glycerol. It is a component of bacterial and eukaryotic glycerophospholi ...

, also called L-α-glycerophosphoric acid. A

triacylglycerol A triglyceride (from ''tri-'' and '' glyceride''; also TG, triacylglycerol, TAG, or triacylglyceride) is an ester derived from glycerol and three fatty acids. Triglycerides are the main constituents of body fat in humans and other vertebrates as ...

having the same fatty acid at carbon 1 and carbon 3 is achiral, but when one of these two is released by hydrolysis, the resulting diacylglyerol is chiral.

References

{{Reflist Stereochemistry