Carbohydrates

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Questions and Answers

Which statement accurately distinguishes between aldoses and ketoses?

  • Aldoses are composed of more than 20 sugar units, whereas ketoses are composed of only one or two sugar units.
  • Aldoses contain a ketone functional group at the end of the carbon chain, whereas ketoses contain an aldehyde functional group in the middle.
  • Aldoses are produced from carbon dioxide and water through hydrolysis, while ketoses are produced through dehydration.
  • Aldoses contain an aldehyde functional group at the end of the carbon chain, whereas ketoses contain a ketone functional group in the middle. (correct)

What is the significance of a chiral center in the context of carbohydrates?

  • It is the center where energy is stored within the carbohydrate molecule.
  • It determines whether a carbohydrate is a monosaccharide or a polysaccharide.
  • It allows carbohydrates to be covalently linked with proteins.
  • It is the carbon atom around which there are four different functional groups, enabling stereoisomerism. (correct)

How are glycoproteins and proteoglycans formed?

  • Through the combination of multiple monosaccharide units.
  • Through the process of photosynthesis.
  • By creating mirror images of carbohydrate molecules.
  • By covalently linking carbohydrates with proteins. (correct)

If a molecule has the same molecular formula but a different spatial arrangement of atoms, it is called a what?

<p>Stereoisomer (A)</p>
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Which of the following is an example of a polysaccharide, based on the information provided?

<p>Amylopectin (A)</p>
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Optical isomerism is a form of stereoisomerism. What is the relationship between molecules exhibiting optical isomerism?

<p>They are mirror images of each other. (C)</p>
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Which of the following is not a primary function of carbohydrates in biological systems?

<p>Enzymatic catalysis (C)</p>
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What distinguishes a disaccharide from a polysaccharide?

<p>A disaccharide consists of two sugar units covalently bonded, while a polysaccharide consists of many (more than 20) sugar units covalently bonded (A)</p>
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Based on the information, what is produced during photosynthesis?

<p>Carbohydrates (D)</p>
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Which of the following correctly lists the molecules from smallest to largest, based on their number of sugar units?

<p>Monosaccharide &lt; Disaccharide &lt; Oligosaccharide &lt; Polysaccharide (B)</p>
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Considering the structure of carbohydrates with multiple chiral centers, which carbon atom is used to determine if the molecule is a D or L stereoisomer?

<p>The carbon furthest from the carbonyl group. (D)</p>
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What distinguishes alpha-D-glucose from beta-D-glucose?

<p>The position of the hydroxyl group on the anomeric carbon. (C)</p>
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Which of the following is a key characteristic of the relationship between D and L stereoisomers of a carbohydrate?

<p>They are enantiomers and mirror images of each other. (C)</p>
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If two glucose molecules combine through a 1-4 glycosidic bond, what disaccharide is formed?

<p>Maltose (A)</p>
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In what form are natural carbohydrates typically found?

<p>Polymers (B)</p>
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What structural feature defines whether a polysaccharide is classified as a homopolysaccharide or a heteropolysaccharide?

<p>The identity of the constituent monosaccharide subunits. (D)</p>
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What is the role of enzymes in carbohydrate chemistry?

<p>Enzymes are specific for reactions involving particular carbohydrates. (A)</p>
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Which of the following best describes the equilibrium that exists for sugars in solution?

<p>Sugars exist in equilibrium between linear and cyclic forms. (D)</p>
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In the formation of a glycosidic bond, which two functional groups typically react?

<p>An anomeric carbon and a hydroxyl group. (A)</p>
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Where are Glycogen branched found?

<p>Liver and muscles (B)</p>
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What type of linkage primarily connects glucose monomers in glycogen?

<p>α(1-4) linkages (D)</p>
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Which characteristic of cellulose makes it difficult for most animals to utilize as a primary fuel source?

<p>Its β(1-4) glycosidic bonds (D)</p>
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What is the primary structural difference between amylose and amylopectin?

<p>Amylopectin is branched and amylose is unbranched. (B)</p>
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What is the approximate frequency of branching (α1-6 linkages) in amylopectin?

<p>Every 24-30 residues (B)</p>
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Which of the following describes the role of fungi, protozoa, and bacteria in cellulose metabolism?

<p>They secrete cellulase, which breaks down cellulose into glucose. (D)</p>
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Which property of cellulose contributes to its structural role in plants?

<p>Tough and water-insoluble structure (A)</p>
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Which agricultural practice is considered unsustainable due to the potential for alternative uses of plant material?

<p>Burning crops after harvest (D)</p>
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What critical function does glycogen serve in animals?

<p>Main storage polysaccharide (B)</p>
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Which statement accurately describes the molecular weight of glycogen?

<p>It reaches several million due to being densely packed. (A)</p>
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What is the role of cellulases in the context of biomass fermentation?

<p>To break down cellulose into fermentable sugars. (B)</p>
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Which of the following best explains why chitin is considered a tough but flexible material?

<p>The β(1-4) linkages provide strong, yet pliable, extended fibers similar to cellulose. (C)</p>
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What key enzymatic process is used to convert chitin into chitosan?

<p>Deacetylation, to remove acetyl groups. (D)</p>
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Vertebrates are unable to digest chitin. What structural feature of chitin is responsible for this?

<p>Its insolubility and the β(1-4) glycosidic bonds are resistant to vertebrate enzymes. (D)</p>
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What is the fundamental structural difference between chitin and chitosan?

<p>Chitosan lacks N-acetyl groups on its glucosamine monomers, while chitin possesses them. (A)</p>
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In what capacity is chitin utilized in the medical field, according to the information?

<p>As a substance used in surgical sutures and drug delivery systems. (A)</p>
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Where is chitin typically found in nature?

<p>In the exoskeletons of arthropods and cell walls of fungi. (B)</p>
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What role do chitinase enzymes play in the breakdown of chitin?

<p>They hydrolyze chitin's glycosidic bonds, breaking it down. (C)</p>
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Individuals with increased expression of chitin-degrading enzymes might be more susceptible to which of the following conditions?

<p>Allergies and asthma. (B)</p>
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Chitin is considered the second most abundant polysaccharide on Earth. What implication does this have for global ecology?

<p>It significantly contributes to the carbon cycle through decomposition. (A)</p>
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How do endochitinases differ from exochitinases in their mechanism of action?

<p>Endochitinases break internal bonds within chitin chains, while exochitinases digest from the ends. (A)</p>
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Which component of the ECM is primarily responsible for providing strength and elasticity to tissues?

<p>Elastin (C)</p>
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How do some tumor cells exploit the ECM to facilitate invasion into tissues?

<p>By secreting heparinase to degrade the ECM (C)</p>
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What is the main function of syndecans, a type of integral membrane protein, in relation to the ECM?

<p>To serve as proteoglycans that span the cell membrane (D)</p>
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Which of the following best describes the role of the ECM in relation to individual cells?

<p>It permits nutrient and oxygen diffusion while providing both structural support and acting as a recognition site. (C)</p>
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How do cells in connective tissues primarily interact with the ECM?

<p>Via heteropolysaccharides, fibrillar collagens, elastin, and fibronectins for movement. (C)</p>
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How do integrins contribute to cell-ECM interactions?

<p>They act as receptors for extracellular proteoglycans. (B)</p>
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In epithelial cells, what role do specialized collagens and laminins play in relation to the ECM?

<p>They contribute to a smooth, strong surface. (D)</p>
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What is the primary role of the proteins that link the cellular cytoskeleton to the ECM?

<p>To transmit signals into the cell, regulating cell growth, mobility, apoptosis, and wound healing (B)</p>
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How does the composition of the ECM typically vary between different cell types?

<p>Cells in different tissues have different ECM compositions. (B)</p>
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What is the composition of the ECM?

<p>Composed of an interwoven network of polysaccharides, proteoglycans, and proteins (B)</p>
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What characteristic distinguishes hyaluronan from other glycosaminoglycans (GAGs)?

<p>It is non-sulfated and consists of very long chains, not typically linked to proteins. (A)</p>
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What is the primary role of glycosaminoglycans (GAGs) in the extracellular matrix (ECM)?

<p>To form a meshwork with fibrous proteins, contributing to tissue structure, lubrication, and cell adhesion. (D)</p>
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Which of the following monomers is a component of the repeating disaccharide units found in glycosaminoglycans?

<p>N-acetylglucosamine (D)</p>
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Which tissue or structure relies on chondroitin sulfate for its tensile strength?

<p>Cartilage, tendons, ligaments, heart valves, and walls of the aorta (C)</p>
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In which of the following locations is keratan sulfate primarily found?

<p>Cornea, cartilage, bone, horns, hair, hooves, nails, and claws (C)</p>
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What role do sperm-secreted hyaluronidase enzymes play in fertilization?

<p>They facilitate sperm penetration of the ovum. (B)</p>
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Which of the following is a key function of hyaluronan in the human body?

<p>Lubricating synovial fluid in joints. (B)</p>
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What is the significance of GAGs being attached to proteins?

<p>It modulates their interactions and functions within the ECM. (A)</p>
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Which structure within the eye benefits from the presence of specific glycosaminoglycans?

<p>Vitreous humor (C)</p>
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Which GAG contributes to the structural integrity and function of the walls of the aorta?

<p>Chondroitin sulfate (C)</p>
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Which characteristic distinguishes heparin sulfate from heparin?

<p>Heparin sulfate is attached to proteins. (B)</p>
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What is the molecular weight range of heparin?

<p>3-40 kDa (A)</p>
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How do glycoconjugates function as information carriers?

<p>Through communication between cells and their surroundings, recognition of signal molecules, and labeling proteins for transport and degradation. (D)</p>
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What is the primary mechanism by which heparin prevents blood clotting?

<p>By activating the protease inhibitor antithrombin. (C)</p>
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Which of the following is a function of heparin and heparan sulfate related to pathogens?

<p>Coating viruses and bacteria to decrease their virulence. (D)</p>
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What is a common structural characteristic of proteoglycans?

<p>A heteropolysaccharide joined to a polypeptide. (D)</p>
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What is a key characteristic of glycosaminoglycan (GAG) chains in proteoglycans?

<p>They are long, linear, and negatively charged. (A)</p>
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What is the main role of proteoglycans within the extracellular matrix (ECM)?

<p>Acting as a major structural component. (B)</p>
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Which statement correctly describes the structure of Syndecans and Glypicans?

<p>Syndecans have a transmembrane domain, while Glypicans are anchored via a GPI anchor. (C)</p>
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What broader biological process is regulated by the binding of heparin and heparan sulfate to various cells?

<p>Regulation of development and formation of blood vessels. (B)</p>
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What role do viral proteins' heavy glycosylation play in the context of the host's immune system?

<p>Helps evade the immune system. (A)</p>
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In glycoproteins, via which carbon atom is the carbohydrate attached to the protein?

<p>The anomeric carbon. (D)</p>
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What role do carbohydrates play in protein-protein recognition?

<p>They play a role in protein-protein recognition. (C)</p>
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What is the primary function of lipopolysaccharides (LPS) in Gram-negative bacteria?

<p>Providing structural support to the cell wall and triggering the immune response (B)</p>
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How does the carbohydrate composition of glycolipids in vertebrates relate to blood groups?

<p>It determines blood groups. (D)</p>
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What is the role of the lipid A portion of bacterial lipopolysaccharides (LPS)?

<p>Acting as an endotoxin. (C)</p>
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What is the nature of the linkage between the oligosaccharide chains and the protein in mucins?

<p>O-linked, serine or threonine residues (B)</p>
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Which components can glycolipids be found in?

<p>Parts of plant and animal cell membranes. (C)</p>
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Which of the following is MOST accurate about the glycosylation of bacterial proteins?

<p>Only some bacteria glycosylate few of their proteins. (D)</p>
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How do lipopolysaccharides contribute to infections caused by some bacteria?

<p>By triggering toxic shock syndrome. (B)</p>
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Flashcards

What defines an aldose?

Aldoses have a carbonyl group (C=O) at the end of the carbon chain, making them aldehydes.

What defines a ketose?

Ketoses have a carbonyl group (C=O) in the middle of the carbon chain, making them ketones.

What are stereoisomers?

Molecules with the same molecular formula but different spatial arrangements.

What is optical isomerism?

A form of stereoisomerism where molecules are mirror images of each other.

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What is a monosaccharide?

One sugar unit; the simplest form of carbohydrate.

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What is a disaccharide?

Two monosaccharide units covalently bonded together.

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What is an oligosaccharide?

Several sugar units covalently bonded together.

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What is a polysaccharide?

A carbohydrate chain of more than 20 sugar units covalently bonded together.

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What is a chiral center?

Carbon atom bonded to four different functional groups.

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What are glycoproteins and proteoglycans?

Carbohydrates can be covalently linked with proteins.

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What are enantiomers?

Stereoisomers that are non-superimposable mirror images of each other.

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D or L configuration

In molecules with multiple chiral centers, the carbon furthest from the carbonyl group determines if the molecule is D or L.

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What are anomers?

A mixture of α and β anomers.

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Glycosidic bond

Formed when the hydroxyl group on the anomeric carbon reacts with another hydroxyl group on another molecule, joining the sugars together.

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Homopolysaccharides

Polymers composed of the same monosaccharide building block.

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Heteropolysaccharides

Polymers composed of different monosaccharide building blocks.

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Where are maltose, sucrose, and lactose found?

Starchy foods, dates, milk.

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Carb structures

Linear or cyclic structures that carbs can form.

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What is Glycogen?

Storage polysaccharides found in animals; a branched homopolysaccharide of glucose.

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What is Cellulose?

Structural carbohydrates with glucose monomers forming β(1-4) linked chains; the most abundant polysaccharide in nature.

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What is starch?

A mix of two homopolysaccharides of glucose that functios as a main storage polysaccharides in plant

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What is Amylose?

Unbranched glucose polymer linked by α(1-4) residues.

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What is Amylopectin?

Branched glucose polymer linked by α(1-4) residues with α(1-6) branch points occurring every 24-30 residues.

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What are cellulases?

enzymes that can hydrolyze cellulose linkages

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Cellulose Structure

In cellulose, fibrous, water-insoluble structure which makes it a difficult substrate to act on

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How does Glycogen branch?

Homopolysaccharide of glucose with branch points with (α1-6) linkers every 8-12 residues

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What are H bonds?

Form between adjacent monomers and additional ones form between chains of cellulose.

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What is Chitin?

A linear heteropolysaccharide made of glucosamine and N-acetylglucosamine units.

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Chitin's Abundance

Chitin is the second most abundant polysaccharide on Earth.

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What is Chitosan?

Chitosan is a linear homopolysaccharide of N-acetylglucosamine.

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Chitin Deacetylation

Treatment with chitin deacetylase removes acetyl groups from chitin.

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Chitin Fibers

Chitin forms extended fibers similar to cellulose.

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Chitin Properties

Chitin is hard, insoluble, and indigestible by vertebrates.

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What are Chitinases?

Enzymes that break down chitin chains.

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Chitinase and Allergies

Increased chitinase expression is linked to asthma and allergies.

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Chitin Location

Chitin is found in mushroom cell walls and arthropod exoskeletons.

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Chitin Applications

Chitin can be converted into chitosan for drug delivery, surgical sutures, and thickening agents.

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ECM function

Gel-like substance that holds cells together.

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ECM: Protection

Provides strength and elasticity to protect cells, located just outside the plasma membrane.

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ECM barrier function

Barrier function that allows nutrients and oxygen to diffuse to individual cells, while also containing recognition sites.

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ECM Composition

Made of an interwoven network of polysaccharides, proteoglycans, and proteins.

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ECM Variation

Cells in different tissues have different ECM compositions; connective tissues include heteropolysaccharides, fibrillar collagens, elastin, and fibronectin.

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Syndecans

some integral membrane proteins which go all the way through the membrane

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Integrins

Integral membrane proteins that are receptors for extracellular proteoglycans.

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ECM Signaling

Proteins link cellular cytoskeleton to ECM and transmit signals into the cell to regulate cell growth, cell mobility, apoptosis, and wound healing.

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ECM & Cancer

Physical barrier in tissues; can be degraded by tumor cells secreting heparinase.

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Roles of ECM

Cell growth, cell mobility, apoptosis, wound healing.

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What are Glycosaminoglycans (GAGs)?

Heteropolysaccharides that are a major component of the extracellular matrix (ECM).

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What is the function of GAGs in the ECM?

GAGs form a meshwork with fibrous proteins in the ECM, important for connective tissue, joint lubrication, and holding the ECM and cells together.

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What is the structure of GAGs?

Linear polymers of repeating disaccharide units; each monomer contains either N-acetylglucosamine or N-acetylgalactosamine.

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What is Hyaluronan?

Found in all tissues and fluids in humans; unusual because it is non-sulfated and has very long chains, not usually linked to proteins; lubricates synovial fluid and gives connective tissue strength and elasticity.

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What is Chondroitin sulfate?

Gives tensile strength to cartilage, tendons, ligaments, heart valves, and walls of the aorta; found attached to proteins.

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What is Keratan sulfate?

Found in the cornea, cartilage, bone, horns, hair, hooves, nails, and claws; found attached to proteins.

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Glycoconjugates

A combination of protein or lipids that have carbohydrates attached

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Heparin

Linear polymer, varies in size from 3-40kDa.

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Heparan sulfate

A type of glycan similar to heparin but linked to proteins.

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Iduronic acid 2-sulfate functions

Regulates development and blood vessel formation by binding to cells, can also bind to and reduce the virulence of viruses and bacteria.

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Proteoglycans

Proteins with one or more covalently attached glycosaminoglycan (GAG) chain(s). Polysaccharide is major component. Chains are long, linear, and negatively charged

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Heparin's role in blood clotting

Inhibits blood clot formation by activating antithrombin, a protease inhibitor.

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Two families of proteoglycans

Syndecans and Glypicans

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Glycoconjugates main role

Communication between cells and their surroundings, recognition sites for signal molecules, and labeling proteins for transport and degradation.

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Molecules with highest -ve density

Biomolecules possessing the greatest density of negative charge due to sulfate groups.

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Proteoglycans' location

A major component of all ECMs (extracellular matrices)

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Glycolipids

Lipids with covalently bound oligosaccharides.

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Glycolipids determine blood groups

In vertebrates, the carbohydrate composition of glycolipids determines blood groups.

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Bacterial Lipopolysaccharides

Lipopolysaccharides covering the peptidoglycan layer in gram-negative bacteria.

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Lipid A (endotoxin)

The lipid A portion of bacterial lipopolysaccharides, acts as a toxin.

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Glycoproteins

Proteins with small oligosaccharides attached via the anomeric carbon of a carbohydrate.

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Role of Glycoproteins

Carbohydrates attached to proteins for recognition.

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Glycosylation in viruses

Heavily glycosylated viral proteins help viruses evade the immune system.

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N-linked/O-linked

Serine is linked via hydroxyl group; asparagine via amide group.

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Bacterial Lipopolysaccharides toxicity

Responsible for toxic shock syndrome associated with some bacterial infections.

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Mucins

Mucins are glycoproteins that contain large numbers of O-linked oligosaccharide chains.

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Study Notes

Glycolipids

  • Lipids with covalently bound oligosaccharide.
  • Found in plant and animal cell membranes.
  • In vertebrates, carbohydrate composition of glycolipids determines blood groups.
  • In Gram-negative bacteria, lipopolysaccharides cover the peptidoglycan layer.
  • Immune system targets bacterial lipopolysaccharides.
  • Lipid A portion of bacterial lipopolysaccharides is known as endotoxin.
  • Bacterial lipopolysaccharides are responsible for toxic shock syndrome associated with some bacterial infections.

Glycoproteins

  • Proteins with small oligosaccharides attached.
  • Carbohydrate is attached via its anomeric carbon.
  • Present in mammalian proteins.
  • Carbohydrates play a role in protein-protein recognition.
  • Only some bacteria glycosylate a few of their proteins.
  • Viral proteins are heavily glycosylated, which helps evade the immune system.
  • N-linked/O-linked: serine involves an alcohol group; asparagine involves an amide group.
  • Mucins contain large numbers of O-linked oligosaccharide chains.

Glycoconjugates

  • Proteins or lipids that have carbohydrates attached.
  • Primary function is as information carriers.
  • Facilitate communication between cells + surroundings.
  • Act as recognition sites for signal molecules.
  • Label proteins for transport and degradation.

Heparin and Heparan Sulfate

  • Heparin is a linear polymer, with a molecular weight between 3-40 kDa.
  • Heparan sulfate is similar to heparin but is attached to proteins.
  • They both prevent blood clotting by activating the protease inhibitor antithrombin.
  • They bind to various cells and regulate development and formation of blood vessels.
  • They can bind to viruses and bacteria, coating them to decrease their virulence.
  • Heparan sulfate has the highest negative charge density of biomolecules.
  • Iduronic acid 2-sulfate is a component of Heparin and Heparan Sulfate.

Proteoglycans

  • Heteropolysaccharides joined to a polypeptide.
  • Polysaccharide is a major component.
  • Usually structured as a core protein with an attached GAG chain.
  • Attached chains are long, linear, and negatively charged.
  • They a major component of all ECMs.
  • Two families of proteoglycans include Syndecan and Glypican.

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