Prostaglandins Classification PDF

Created by Turbolearn AI Introduction to Prostaglandins The lecture discusses prostaglandins, which are a group of lipids that have hormone-like effects in animals. Classification of Prostaglandins The classification of prostaglandins is based on their chemical structure. Prostaglandins are...

Created by Turbolearn AI Introduction to Prostaglandins The lecture discusses prostaglandins, which are a group of lipids that have hormone-like effects in animals. Classification of Prostaglandins The classification of prostaglandins is based on their chemical structure. Prostaglandins are a group of eicosanoids, which are derived from 20- carbon fatty acids. The classification of prostaglandins can be divided into two main categories: Prostanoic acid derivatives: This category includes prostaglandins such as PGA, PGB, PGC, and PGD. Leukotrienes and lipoxins: This category includes leukotrienes and lipoxins, which are also derived from 20-carbon fatty acids. The prostanoic acid derivatives can be further divided into three subcategories: Subcategory Description Prostaglandins Includes PGA, PGB, PGC, and PGD Prostacyclins Includes PGI, which is also known as prostacyclin Thromboxanes Includes TXA, which is also known as thromboxane Chemical Relations between Prostaglandins The prostaglandins can be converted into each other through different chemical reactions. For example: PGA can be converted into PGB through reduction PGA can be converted into PGC through acid-catalyzed reaction PGA can be converted into PGD through base-catalyzed reaction The chemical relations between prostaglandins can be summarized as follows: Page 1  Created by Turbolearn AI PGA can be converted into PGB, PGC, and PGD through different chemical reactions PGB can be converted into PGC and PGD through different chemical reactions PGC can be converted into PGD through different chemical reactions Nomenclature of Prostaglandins The nomenclature of prostaglandins is based on their chemical structure. The nomenclature of prostaglandins can be summarized as follows: Prostaglandin Nomenclature Prostaglandin PGA A Prostaglandin PGB B Prostaglandin PGC C Prostaglandin PGD D PGI Prostacyclin Thromboxane TXA A The PG compounds are more soluble in ether. The PG compounds have a specific nomenclature. Nomenclature of PG Compounds The nomenclature of PG compounds is based on the following rules: A refers to the solubility of the compound in ether F refers to the solubility of the compound in phosphate buffer B and D refer to the conversion of PG compounds in the presence of acid or base Definition of PG Compounds The PG compounds are a class of compounds that have a specific structure and properties. They are characterized by their solubility in ether and phosphate buffer. Page 2  Created by Turbolearn AI Types of PG Compounds The following are the different types of PG compounds: PGA: soluble in ether PGF: soluble in phosphate buffer PGB: converted from PGA in the presence of acid PGD: converted from PGA in the presence of base Structure of PG Compounds The structure of PG compounds consists of a five-membered ring with a side chain. The side chain has a specific number of double bonds. Number of Double Bonds The number of double bonds in the side chain of PG compounds is denoted by subscript numerals. The following table shows the number of double bonds in different PG compounds: Compound Number of Double Bonds PGA 1 PGB 1 PGC 2 PGD 2 PGE 2 PGF 3 Position of Double Bonds The position of double bonds in the side chain of PG compounds is specific. The following table shows the position of double bonds in different PG compounds: Page 3  Created by Turbolearn AI Compound Position of Double Bonds PGA C13 and C14 PGB C13 and C14 PGC C13 and C14, C15 and C16 PGD C13 and C14, C15 and C16 PGE C13 and C14, C15 and C16, C17 and C18 PGF C13 and C14, C15 and C16, C17 and C18 Configuration of Double Bonds The double bonds in the side chain of PG compounds have a specific configuration. The configuration can be either cis or trans. The trans configuration is more common in PG compounds. Summary In summary, the PG compounds have a specific nomenclature, structure, and properties. The nomenclature is based on the solubility of the compound in ether and phosphate buffer. The structure consists of a five-membered ring with a side chain that has a specific number of double bonds. The double bonds have a specific position and configuration.## Prostaglandins P G Classification The classification of Prostaglandins P G is based on the number of double bonds in the molecule. The general structure of PG consists of a five-membered ring with two side chains. PG Structure The structure of PG can be represented as follows: A five-membered ring containing a keto group and a hydroxyl group Two side chains, one containing a carboxylic acid group Double Bond Positions The positions of the double bonds in the PG molecule are crucial in determining its classification. The double bonds can be located at different positions, including: Page 4  Created by Turbolearn AI 13-14 position: The first double bond is located between the 13th and 14th carbon atoms 5-6 position: The second double bond is located between the 5th and 6th carbon atoms 17-18 position: The third double bond is located between the 17th and 18th carbon atoms PG Classification Table The classification of PG is summarized in the following table: PG Type Number of Double Bonds Double Bond Positions PGE1 1 13-14 PGE2 2 13-14, 5-6 PGE3 3 13-14, 5-6, 17-18 Stereochemistry The stereochemistry of PG is also important, as it affects the molecule's properties and functions. The stereochemistry of a molecule refers to the three-dimensional arrangement of its atoms in space. Key Points The key points to remember about PG classification are: The number of double bonds in the molecule The positions of the double bonds The stereochemistry of the molecule The presence of a hydroxyl group at the 15th position in the side chain PG Synthesis The synthesis of PG involves the formation of the five-membered ring and the addition of the side chains. The synthesis of PG is a complex process that involves multiple steps and reactions. Page 5  Created by Turbolearn AI Conclusion of PG Classification In conclusion, the classification of PG is based on the number of double bonds and their positions in the molecule. Understanding the structure and stereochemistry of PG is crucial in determining its properties and functions.## Introduction to PG and its Derivatives The lecture discusses the conversion of PG to its derivatives, including PGF. The conversion involves the reduction of the keto group to a hydroxyl group. Conversion of PG to PGF The conversion of PG to PGF involves the reduction of the keto group to a hydroxyl group. This can be represented by the following equation: P G → P GF Alpha and Beta Forms of PGF PGF can exist in two forms: alpha and beta. The alpha form has the hydroxyl group below the plane of the molecule, while the beta form has the hydroxyl group above the plane of the molecule. The alpha form of PGF is defined as the form where the hydroxyl group is below the plane of the molecule. The beta form of PGF is defined as the form where the hydroxyl group is above the plane of the molecule. Stereochemistry of PGF The stereochemistry of PGF is important in determining its properties and functions. The hydroxyl group can be either above or below the plane of the molecule, resulting in different alpha and beta forms. Prefixes in PG Nomenclature The prefixes used in PG nomenclature are important in determining the structure and properties of the molecule. Some common prefixes include: Dihydro: indicates the saturation of a double bond Hydro: indicates the addition of a hydrogen atom Page 6  Created by Turbolearn AI Prefix Meaning Dihydro Saturation of a double bond Hydro Addition of a hydrogen atom Example: 13,14-Dihydro PGF2 The structure of 13,14-Dihydro PGF2 can be determined by first drawing the structure of PGF2 and then adding hydrogen atoms to the double bond at positions 13 and 14. Key Points to Remember PG can be converted to PGF through reduction of the keto group PGF can exist in alpha and beta forms The stereochemistry of PGF is important in determining its properties and functions Prefixes in PG nomenclature are important in determining the structure and properties of the molecule Table of PG Derivatives Derivative Structure Properties Important in 5-membered ring determining PGF2 with keto group properties and functions Saturation of Resulting in a 13,14-Dihydro PGF2 double bond at different structure positions 13 and 14 and properties The lecture discusses the structure and formation of prostaglandins, a group of lipids that have hormone-like effects in the body. Formation of Prostaglandins To form a prostaglandin, we start with a 5-membered ring structure, which is the base of the molecule. The double bond is then introduced at the 13th and 14th positions. Page 7  Created by Turbolearn AI The double bond is a type of covalent bond where two pairs of electrons are shared between two atoms. The hydrogenation of the double bond at the 13th and 14th positions results in the formation of a saturated compound. Prefixes in Prostaglandin Nomenclature The prefixes used in prostaglandin nomenclature are: Dihydro: indicates the formation of a new double bond Deoxy: indicates the removal of an oxygen atom Nor: indicates the replacement of a methyl group with a nitrogen atom Deoxy Prostaglandins To form a deoxy prostaglandin, we remove the oxygen atom from the hydroxyl group at the 11th position. Position Group 11 Hydroxyl group 13-14 Double bond Dihydro Prostaglandins To form a dihydro prostaglandin, we introduce a new double bond at the 2nd and 3rd positions. Position Group 2-3 Double bond 13-14 Double bond Nor Prostaglandins To form a nor prostaglandin, we replace the methyl group at the 8th position with a nitrogen atom. Page 8  Created by Turbolearn AI Position Group 8 Methyl group replacedwithnitrogen 13-14 Double bond Stereochemistry The stereochemistry of the prostaglandin molecule is important, as it can affect the biological activity of the compound. Stereochemistry refers to the three-dimensional arrangement of atoms in a molecule. The trans configuration is often preferred in prostaglandin synthesis, as it can result in a more biologically active compound. Conclusion In conclusion, the formation of prostaglandins involves the introduction of double bonds and the removal or replacement of various functional groups. Understanding the nomenclature and stereochemistry of prostaglandins is important for the synthesis and characterization of these compounds.## Introduction to Prostaglandins The lecture discusses the concept of prostaglandins, which are a group of lipids that have hormone-like effects in the body. Understanding Prostaglandin Nomenclature To understand the nomenclature of prostaglandins, it is essential to know the meaning of certain prefixes and suffixes. The prefix "di" refers to the presence of two double bonds in the molecule. The prefix "tri" refers to the presence of three double bonds in the molecule. The prefixes are used to describe the number of double bonds in the molecule. Types of Prostaglandins There are several types of prostaglandins, including: Page 9  Created by Turbolearn AI PGE1: This type of prostaglandin has a single double bond between the 13th and 14th carbon atoms. PGE2: This type of prostaglandin has two double bonds, one between the 13th and 14th carbon atoms and another between the 5th and 6th carbon atoms. Modifying Prostaglandin Molecules To modify prostaglandin molecules, certain groups can be added or removed. The hydroxyl group −OH can be removed through a process called deoxylation. The methylene group −CH2− can be replaced with an oxygen atom to form a carbonyl group C = O. Prefixes and Their Meanings The following table summarizes the meanings of certain prefixes: Prefix Meaning di two double bonds tri three double bonds deoxy removal of an oxygen atom oxo replacement of a methylene group with a carbonyl group Examples of Prostaglandin Modification The following are examples of how prostaglandin molecules can be modified: 11-Deoxy-11-oxo-PGE1: This molecule has a deoxy group at the 11th carbon atom and an oxo group at the same position. 2,3,4,5-Tetranor-PGE1: This molecule has a tetranor group, which means that four carbon atoms have been removed from the molecule. Understanding the Tetranor Prefix The tetranor prefix refers to the removal of four carbon atoms from the molecule. This can be done by removing a methylene group from the ring structure of the prostaglandin molecule. Removing Methylene Groups Page 10  Created by Turbolearn AI Methylene groups can be removed from the ring structure of prostaglandin molecules through a process called nor modification. This involves the removal of a methylene group from the ring, resulting in a nor-modified molecule. Examples of Nor Modification The following are examples of how nor modification can be applied to prostaglandin molecules: 10-Nor-PGE1: This molecule has a nor group at the 10th carbon atom, which means that a methylene group has been removed from the ring structure. 11-Deoxy-10-nor-PGE1: This molecule has a deoxy group at the 11th carbon atom and a nor group at the 10th carbon atom.## Introduction to Deoxygenation Deoxygenation refers to the removal of an oxygen atom from a molecule. In the context of the given lecture, deoxygenation involves the removal of a hydroxyl group −OH from a specific position in a molecule. Understanding the Process The process of deoxygenation can be broken down into several steps: Removal of the hydroxyl group from the 11th position Removal of a carbon atom from the 10th position Formation of a four-membered ring Key Concepts The following are key concepts related to deoxygenation: Deoxygenation: the removal of an oxygen atom from a molecule Hydroxyl group: a functional group consisting of a hydrogen atom bonded to an oxygen atom Four-membered ring: a ring structure consisting of four atoms Homologation Homologation refers to the addition of a methyl group to a molecule. In the context of the lecture, homologation involves the addition of a methyl group to the 9th position of a molecule. Homologation is the process of adding a methyl group to a molecule, resulting in the formation of a new compound with a longer carbon chain. Page 11  Created by Turbolearn AI Nomenclature The nomenclature of the resulting compound is based on the position of the added methyl group. For example: Position Nomenclature 9 9α 10 10α Examples The lecture provides an example of a molecule undergoing deoxygenation and homologation: The molecule has a hydroxyl group at the 11th position, which is removed through deoxygenation The resulting molecule has a methyl group added to the 9th position through homologation, resulting in the formation of a new compound with the nomenclature 9α Summary In summary, deoxygenation and homologation are important processes in organic chemistry that involve the removal and addition of functional groups to molecules. Understanding these processes is crucial for the synthesis and identification of new compounds. Deoxygenation: removal of an oxygen atom from a molecule Homologation: addition of a methyl group to a molecule Nomenclature: the naming of compounds based on their structure and position of functional groups Page 12