Prochirality: Difference between revisions

Latest revision as of 11:35, 15 February 2025

Concept in stereochemistry

Prochirality is a concept in stereochemistry that describes a situation where a molecule is not chiral but can become chiral through a single alteration, such as the replacement of an atom or group. This concept is important in the study of enzyme reactions and asymmetric synthesis.

Definition[edit]

A molecule is considered prochiral if it can be converted from an achiral to a chiral molecule in a single step. This typically involves the introduction of a new stereocenter or the conversion of a prochiral center into a chiral center.

Prochiral Centers[edit]

A prochiral center is an atom in a molecule that can be converted into a chiral center by changing one of its substituents. For example, a carbon atom bonded to two identical groups and two different groups is a prochiral center. By replacing one of the identical groups with a different group, the carbon becomes a chiral center.

Prochirality in Enzymatic Reactions[edit]

Enzymes often interact with prochiral substrates, selectively converting them into chiral products. This selectivity is crucial in biochemistry, where the chirality of molecules can affect their biological activity. Enzymes can distinguish between the two faces of a prochiral molecule, leading to the formation of a specific enantiomer.

Prochirality in Asymmetric Synthesis[edit]

In asymmetric synthesis, prochiral molecules are often used as starting materials. The goal is to selectively produce one enantiomer over the other, which is achieved by using chiral catalysts or reagents that can differentiate between the two faces of the prochiral molecule.

Applications[edit]

Prochirality is a key concept in the design of pharmaceuticals, where the chirality of a drug can significantly influence its efficacy and safety. Understanding prochirality allows chemists to design synthetic routes that produce the desired enantiomer of a drug.

Related pages[edit]

@@ Line 1: / Line 1: @@
-== Prochirality ==
+{{Short description|Concept in stereochemistry}}
+{{Use dmy dates|date=October 2023}}
-Prochirality is a concept in chemistry that refers to the presence of a chiral center in a molecule that can be converted into a stereogenic center through a single chemical reaction. The term "prochiral" is derived from the words "pro" (meaning "before") and "chiral" (referring to a molecule that is not superimposable on its mirror image). Prochirality plays a significant role in understanding the stereochemistry and reactivity of organic compounds.
+'''Prochirality''' is a concept in [[stereochemistry]] that describes a situation where a molecule is not chiral but can become chiral through a single alteration, such as the replacement of an atom or group. This concept is important in the study of [[enzyme]] reactions and [[asymmetric synthesis]].
-=== Definition ===
+==Definition==
+A molecule is considered '''prochiral''' if it can be converted from an achiral to a chiral molecule in a single step. This typically involves the introduction of a new [[stereocenter]] or the conversion of a prochiral center into a chiral center.
-A prochiral center is an atom in a molecule that is bonded to four different substituents, but lacks chirality due to the presence of a plane of symmetry or an internal symmetry element. This means that the molecule itself is not chiral, but it possesses the potential to become chiral under certain conditions. Prochirality is often associated with carbon atoms, but it can also occur in other elements such as sulfur, nitrogen, and phosphorus.
+==Prochiral Centers==
+A prochiral center is an atom in a molecule that can be converted into a chiral center by changing one of its substituents. For example, a carbon atom bonded to two identical groups and two different groups is a prochiral center. By replacing one of the identical groups with a different group, the carbon becomes a chiral center.
-=== Conversion to Chirality ===
+==Prochirality in Enzymatic Reactions==
+[[File:Prochirality V.1.svg|thumb|right|Illustration of prochirality in a molecule.]]
+Enzymes often interact with prochiral substrates, selectively converting them into chiral products. This selectivity is crucial in [[biochemistry]], where the chirality of molecules can affect their biological activity. Enzymes can distinguish between the two faces of a prochiral molecule, leading to the formation of a specific enantiomer.
-The conversion of a prochiral center into a stereogenic center can be achieved through a chemical reaction known as a prochiral-to-chiral transformation. This transformation involves breaking the symmetry of the prochiral center, resulting in the formation of two enantiomers (mirror-image isomers) that are non-superimposable. The most common prochiral-to-chiral transformations involve the addition or removal of a substituent from the prochiral center.
+==Prochirality in Asymmetric Synthesis==
+In [[asymmetric synthesis]], prochiral molecules are often used as starting materials. The goal is to selectively produce one enantiomer over the other, which is achieved by using chiral catalysts or reagents that can differentiate between the two faces of the prochiral molecule.
-=== Importance in Organic Chemistry ===
+==Applications==
+Prochirality is a key concept in the design of [[pharmaceuticals]], where the chirality of a drug can significantly influence its efficacy and safety. Understanding prochirality allows chemists to design synthetic routes that produce the desired enantiomer of a drug.
-Prochirality is of great importance in organic chemistry as it affects the stereochemistry and reactivity of organic compounds. The presence of a prochiral center in a molecule can lead to the formation of multiple stereoisomers, each with distinct properties and reactivity. Understanding prochirality is crucial in the design and synthesis of chiral drugs, catalysts, and other important organic molecules.
+==Related pages==
-=== Applications ===
-Prochirality finds applications in various fields of chemistry, including drug discovery, asymmetric synthesis, and catalysis. By selectively converting prochiral centers into chiral centers, chemists can control the stereochemistry of a molecule, which is often crucial for its biological activity or desired reactivity. Prochiral-to-chiral transformations are commonly employed in the synthesis of pharmaceuticals, agrochemicals, and other fine chemicals.
-=== Related Concepts ===
-Prochirality is closely related to other concepts in stereochemistry, such as chirality, enantiomers, and diastereomers. Chirality refers to the property of a molecule that is not superimposable on its mirror image. Enantiomers are pairs of molecules that are mirror images of each other and cannot be superimposed. Diastereomers, on the other hand, are stereoisomers that are not mirror images of each other.
-=== Conclusion ===
-Prochirality is a fundamental concept in chemistry that describes the potential for a molecule to become chiral through a single chemical reaction. Understanding prochirality is essential for predicting and controlling the stereochemistry and reactivity of organic compounds. Its applications in drug discovery, asymmetric synthesis, and catalysis make it a crucial area of study in modern chemistry.
-== See Also ==
 * [[Chirality (chemistry)]]
+* [[Stereochemistry]]
 * [[Enantiomer]]
-* [[Diastereomer]]
+* [[Asymmetric synthesis]]
-* [[Stereochemistry]]
-== References ==
-<references />
-[[Category:Chemistry]]
 [[Category:Stereochemistry]]
-[[Category:Organic chemistry]]