25.10 Some Other Important Carbohydrates
2 min read•may 7, 2024
Carbohydrate derivatives are crucial players in biology. , the sugar in , lacks an oxygen atom at the 2' position, making DNA more stable than . This small change has huge implications for genetic information storage.
Amino sugars swap a hydroxyl group for an amino group, usually at the 2' position. These modified sugars, like and , are key components in structures like and cartilage, and play vital roles in cell signaling.
Carbohydrate Derivatives
Structure of 2-deoxyribose in DNA
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- Modified lacks oxygen atom at 2' position compared to
- Ribose has hydroxyl group (-OH) at 2' position
- 2-deoxyribose has hydrogen atom (-H) at 2' position
- Key component of DNA (deoxyribonucleic acid) backbone
- DNA is polynucleotide composed of monomers
- Each nucleotide consists of , 2-deoxyribose, and (, , , )
- Phosphate group and 2-deoxyribose form backbone of DNA strand
- Nitrogenous bases responsible for genetic information
- Absence of 2' hydroxyl group in 2-deoxyribose contributes to DNA stability
- Presence of 2' hydroxyl group in RNA (ribonucleic acid) makes it more susceptible to hydrolysis and degradation compared to DNA
Amino sugars vs typical carbohydrates
- Monosaccharides with amino group (-NH2) replacing one of the hydroxyl groups
- Amino group typically located at 2' position, replacing hydroxyl group
- Examples of amino sugars:
- Glucosamine: derived from glucose, found in chitin (component of arthropod exoskeletons and fungal cell walls)
- Galactosamine: derived from galactose, found in (component of cartilage) and (component of synovial fluid and connective tissue)
- ( or ): complex found in glycoproteins and gangliosides on cell surfaces
- Play important roles in various biological processes
- Components of structural polysaccharides like chitin and glycosaminoglycans
- Involved in cell signaling and recognition as part of glycoproteins and glycolipids on cell surfaces
Deoxy sugars vs amino sugars
- Similarities:
- Both derived from monosaccharides by replacing functional group at specific position
- Both have modified structure compared to parent
- Differences:
- Deoxy sugars have hydrogen atom (-H) replacing hydroxyl group (-OH), typically at 2' position
- Example: 2-deoxyribose, derived from ribose
- Amino sugars have amino group (-NH2) replacing hydroxyl group (-OH), typically at 2' position
- Examples: glucosamine, galactosamine, N-acetylneuraminic acid
- Deoxy sugars have hydrogen atom (-H) replacing hydroxyl group (-OH), typically at 2' position
- Functional differences:
- Deoxy sugars, like 2-deoxyribose, are important components of DNA and contribute to its stability
- Amino sugars involved in various biological structures (chitin, glycosaminoglycans) and processes (cell signaling, recognition)
Carbohydrate Classification and Metabolism
- Monosaccharides: simplest form of carbohydrates, cannot be hydrolyzed into smaller units
- Disaccharides: formed by joining two monosaccharides through a
- Polysaccharides: long chains of monosaccharides linked by glycosidic bonds, serving various functions in organisms
- : series of biochemical processes involved in the breakdown and synthesis of carbohydrates
- : study of the structure, biosynthesis, and biology of saccharides (sugar chains or glycans)
Key Terms to Review (33)
2-deoxyribose: 2-deoxyribose is a monosaccharide that serves as the sugar component in the backbone of DNA molecules. It is a pentose sugar, meaning it contains five carbon atoms, and is characterized by the absence of an oxygen atom at the 2' position compared to the ribose sugar found in RNA.
Adenine: Adenine is a purine-based nitrogenous base that is one of the four fundamental building blocks of nucleic acids, including DNA and RNA. It plays a crucial role in various biochemical processes and is closely associated with the topics of polycyclic aromatic compounds, carbohydrates, and nucleic acids.
Amino Sugar: An amino sugar, also known as an aminosugar or glycosamine, is a monosaccharide (simple sugar) that contains an amino group (NH2) in place of a hydroxyl group (OH) on the sugar molecule. These modified sugars are important structural components of many biomolecules, including glycoproteins, glycolipids, and the polysaccharide chitin.
Carbohydrate Metabolism: Carbohydrate metabolism refers to the biochemical processes that the body uses to convert carbohydrates from the diet into energy that can be utilized by cells. It is a crucial aspect of overall energy production and regulation within the body.
Chitin: Chitin is a natural polysaccharide composed of N-acetylglucosamine units. It is a structural component found in the exoskeletons of arthropods, such as crustaceans and insects, as well as in the cell walls of certain fungi. Chitin's unique properties and abundance in nature make it a versatile and important biomaterial with applications in various fields, including 21.8 Chemistry of Thioesters and Acyl Phosphates: Biological Carboxylic Acid Derivatives and 25.10 Some Other Important Carbohydrates.
Chondroitin Sulfate: Chondroitin sulfate is a complex carbohydrate found in the cartilage, bone, and connective tissues of the body. It is a key structural component that provides cushioning and support to these tissues, making it an important player in the context of other important carbohydrates discussed in this chapter.
Cytosine: Cytosine is a pyrimidine-based nitrogenous base that is one of the four main components of nucleic acids, including DNA and RNA. It plays a crucial role in the structure and function of these genetic materials across various topics in organic chemistry.
Deoxy sugar: A deoxy sugar is a type of carbohydrate in which a hydroxyl group (-OH) is replaced by a hydrogen atom (-H) on one or more carbon atoms. This modification results in a sugar that has one less oxygen atom than its corresponding sugar, making it crucial in various biological processes and structures, especially in nucleic acids.
Deoxyribonucleic acid (DNA): DNA is a molecule that contains the instructions an organism needs to develop, live, and reproduce. It is composed of two long strands forming a double helix structure, where sequences of four types of nucleotides encode genetic information.
Disaccharide: A disaccharide is a type of carbohydrate composed of two monosaccharide units linked together through a glycosidic bond. Disaccharides are an important class of carbohydrates that serve various functions in living organisms, including providing energy and structural support.
DNA: DNA, or deoxyribonucleic acid, is the genetic material that carries the instructions for the development and functioning of living organisms. It is a complex molecule that stores and transmits genetic information, playing a crucial role in various aspects of organic chemistry, including chirality, carbohydrates, and nucleic acids.
Galactosamine: Galactosamine is an amino sugar that is a structural component of various glycoproteins and glycosaminoglycans, which are important biomolecules found in the body. It is closely related to the more common monosaccharide, glucose, and plays a crucial role in several biological processes discussed in the context of 'Some Other Important Carbohydrates'.
Ganglioside: Gangliosides are a class of glycosphingolipids that are found primarily in the cell membranes of nerve cells. They play important roles in cellular recognition, signaling, and adhesion processes within the nervous system.
Glucosamine: Glucosamine is an amino sugar that is a key structural component of glycosaminoglycans, which are long chains of repeating disaccharide units found in the extracellular matrix and joint cartilage. It plays an important role in the context of 'Some Other Important Carbohydrates' as a naturally occurring compound with potential therapeutic applications.
Glycobiology: Glycobiology is the study of the structure, biosynthesis, and biological functions of carbohydrates (or glycans) in biological systems. It encompasses the roles of these complex sugars in cellular processes, development, and disease.
Glycolipid: A glycolipid is a type of lipid molecule that contains a carbohydrate (glyco-) attached to a lipid component. Glycolipids are important structural components of cell membranes and play crucial roles in various biological processes within the context of 'Some Other Important Carbohydrates'.
Glycoprotein: A glycoprotein is a macromolecule composed of a protein covalently bonded to one or more carbohydrate chains, known as glycans. These complex molecules serve a variety of structural and functional roles in living organisms, particularly in cell-cell interactions and cell signaling processes.
Glycosaminoglycan: Glycosaminoglycans (GAGs) are long, unbranched polysaccharides composed of repeating disaccharide units. They are a crucial component of the extracellular matrix and play vital roles in various biological processes within the context of 'Some Other Important Carbohydrates'.
Glycosidic Bond: A glycosidic bond is a covalent bond that connects a carbohydrate (sugar) molecule to another molecule, such as another carbohydrate, a lipid, or a protein. This bond is formed when the hydroxyl group of one molecule reacts with the anomeric carbon of a monosaccharide, creating a new compound with unique properties and functions.
Guanine: Guanine is a purine-based nitrogenous base that is one of the four primary components of nucleic acids, including DNA and RNA. It is a crucial element in the genetic makeup of all living organisms, playing a vital role in various biological processes.
Hyaluronic Acid: Hyaluronic acid is a large, naturally occurring polysaccharide found in the extracellular matrix of various tissues, including the skin, joints, and eyes. It is a key component of the human body that plays crucial roles in hydration, lubrication, and tissue repair.
Monosaccharide: A monosaccharide is the simplest form of carbohydrates, consisting of a single sugar molecule that cannot be hydrolyzed into smaller sugar units. They serve as fundamental building blocks for more complex carbohydrates and are crucial for energy metabolism in living organisms.
Monosaccharide: A monosaccharide is the simplest form of carbohydrate, consisting of a single sugar unit that cannot be broken down into smaller carbohydrate molecules. Monosaccharides are the building blocks of more complex carbohydrates and play a crucial role in various metabolic processes within the body.
N-acetylneuraminic acid: N-acetylneuraminic acid, also known as sialic acid, is a monosaccharide that is an important component of many glycoproteins and glycolipids found in the body. It plays a crucial role in various biological processes, including cell-cell recognition, immune function, and pathogen binding.
NANA: NANA, or N-Acetylneuraminic acid, is a type of sialic acid that is a common component of glycoproteins and glycolipids found in various tissues and bodily fluids. It is an important monosaccharide that plays a crucial role in the context of carbohydrate chemistry and biology.
Nitrogenous Base: A nitrogenous base is a type of organic compound that contains at least one nitrogen atom and is capable of accepting a proton to form a positively charged ion. These bases are essential components of nucleic acids, such as DNA and RNA, and play a crucial role in various biological processes.
Nucleotide: A nucleotide is the basic structural unit of nucleic acids, such as DNA and RNA. It consists of a nitrogenous base, a five-carbon sugar, and a phosphate group. Nucleotides are essential in various biological processes, including DNA replication, transcription, and translation.
Phosphate Group: A phosphate group is a chemical structure consisting of one phosphorus atom covalently bonded to four oxygen atoms. It is a fundamental component in various biomolecules, playing crucial roles in energy storage, cell signaling, and the structural integrity of biological macromolecules.
Polysaccharide: Polysaccharides are large, complex carbohydrate molecules composed of repeating units of monosaccharides linked together. They serve as important structural and storage components in living organisms, particularly in the context of 25.10 Some Other Important Carbohydrates.
Ribose: Ribose is a monosaccharide, a type of simple sugar, that is an essential component of ribonucleic acid (RNA). It is a pentose sugar, meaning it has five carbon atoms, and is the backbone of the RNA molecule, playing a crucial role in various biological processes.
RNA: RNA, or ribonucleic acid, is a crucial biomolecule that plays a central role in the storage and expression of genetic information within cells. It is closely related to DNA, but with some key structural and functional differences that make it an essential component in various biological processes.
Sialic Acid: Sialic acid is a family of acidic monosaccharides that are commonly found as the terminal sugar units of glycoconjugates, such as glycoproteins and glycolipids, on the surface of many cells. These molecules play crucial roles in various biological processes related to the topics of 'Some Other Important Carbohydrates'.
Thymine: Thymine is a pyrimidine-based nitrogenous base that is one of the four essential components of DNA, along with adenine, cytosine, and guanine. It plays a crucial role in the structure and function of nucleic acids, particularly in the context of aromatic heterocycles, carbohydrates, and nucleotides and nucleic acids.