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Tarteel Sabrah Dr.Ma'moun Ahram 7 Faculty of medicine – JU2018 Tarteel Sabrah Tarteel Sabrah Tarteel Sabrah Dr.Ma'moun Ahram Raffinose We talked about monosaccharide, we talked about disaccharide let's get big now . we will talk about oligosaccharide which is basically carbohydrates made of 3 to 10 monosaccharides or sugar residues Raffinose is an example . Raffinose is a trisaccharide that is made of three monosaccharides ( sugar residues) . If you look at structure first one is galactose then glucose and then fructose . from left to right It is Found in beans and vegetables like cabbage, Brussels, sprouts, broccoli, asparagus . And we can't digest raffinose because of Humans lack the Alpha-galactosidase enzyme that is needed to break down raffinose, but intestinal bacteria can ferment it into hydrogen, methane, and other gases but It is not as bad as lactose intolerance. Look at these monosaccharides and how are connected to each other as a practice whenever you see something like this look at each residue and try to identify it is it glucose, galactose and so on identify the anomeric configuration identify the glycosidic linkage between these different subunits Type of glycosidic bond between galactose and glucose [α: 16 ] Type of glycosidic bond between glucose and fructose [β: 12] 1 | P a g e We have oligosaccharide that can be larger and oligosaccharide that can be modified in certain ways so we can use them as antibiotics Oligosaccharides as drugs Streptomycin and erythromycin anticancer agents Doxorubicin Digoxin cardiovascular drug. STRUCTURES NOT TO BE MEMORIZED Polysaccharides polysaccharides basically made of subunits of sugar these monosaccharides or these sugars can be all the same so we call it Homopolysaccharides or can be different and we call them Heteropolysaccharides now in terms of function so they can be classified according to structure homo- or hetero- or they can be classified according to function some polysaccharides are used for storage so whenever we have excess glucose, for example, this glucose can be stored in the form of polysaccharides or these polysaccharides can be structural meaning they form a certain structure rather than produce energy now whenever you look at polysaccharides try to identify what subunits (Monosaccharides) are used to make this polysaccharides how these monosaccharides are linked to each other how big is this polysaccharide(Length) is it branched or is it a straight molecule(Branching) and what is used for structural or storage(purpose). In yellow Features of polysaccharides 2 | P a g e Glycogen one important polysaccharide is glycogen, glycogen is a Homopolysaccharides it is made of just glucose monomers / residues it is also a branch molecule so look here it is electron microscopic image of the hepatocyte liver cell all of these dark dots here are glycogen molecules deposits of glycogen molecule about 90 % of glycogen stored in the liver and 10 % stored in muscles look at the structure right here it is highly branched basically you have subunits of glucose connected to each other in which anomeric form they exist ? alpha α because carbon number one directed downward how are they connected which carbons involves in glycosidic bond 1 and 4 so what you have here a chain of glucose monomers connected by [ α:1 4] then it is a branched molecule and it is [ α:1 6] and this branching 3 | P a g e Starch Glycogen exists in humans as well as animals we have something similar to glycogen in plants that is called starch there are two structures of starch one is known as amylose and the other one known as amylopectin now amylose is a straight molecule not branching , amylopectin is branched so looking like glycogen look at amylose Is it homo or heteropolysaccharide ? Homopolysaccharide consists of repeating units (glucose residues) How they are connected ? [α:1 4]" note : the anomeric form of each monomer is α alpha but the type of linkage is [ α:1 4]" Look at amylopectin is it homo or heteropolysaccharide?- Homopolysaccharide consists of glucose only and the anomeric is alpha α as well and the linkage is [ α:1 4] and it is branched and the branch exists as [ α:1 6] 4 | P a g e Glycogen vs. amylopectin So it looks like glycogen except there is a difference between glycogen and starch in that glycogen branches every 10 is more branched than amylopectin starch every 25 So why is it less branched in plants? for animal, there is less water inside cells relative to plant cells so it needs to be more branched in animal cells than plant cells because there is less water so it crystallized less in plant cells Glycogen Starch Slides : Glycogen vs. amylopectin o Both are made from the same monomer and both are branched. Glycogen exists in animals and amylopectin in plants. o Glycogen is more highly branched. Branch points occur about every 10 residues in glycogen and about every 25 residues in amylopectin. Why is branching important? It makes it more water-soluble and does not crystallize. Easy access to glucose residues. 5 | P a g e Dextran We have another polysaccharide again its Homopolysaccharide and made of glucose residues there is a chain that it is linked by [ α:1 6] an it is also a branched molecule but the branching is variable at carbon number 2, 3 ,4 In general, all previous polysaccharides are used for storage for energy purposes so whenever the body needs energy all it has to do is remove glucose residue from the glycogen and utilize it for metabolism Slides: Dextran A storage polysaccharide Yeast and bacteria -(1-6)-D-glucose with branched chains Branches: 1-2, 1-3, or 1-4 Let's move on the next sugar 6 | P a g e Cellulose Cellulous residues' the same or different ? Same ; what is the anomeric configuration ? beta β configuration rather than alpha α it is not a branch molecule so it's a straight molecule so what is the advantage of having β beta glycosidic bond and the carbons involve one and four [β:1 4] the advantage of having a beta β anomeric glycosidic bond is that the molecule becomes rigid it does not rotate whereas the alpha α glycosidic bond allows for the molecule to bent so we can store as many glucose molecules in as little space as possible whereas in cellulose the beta β glycosidic bond makes the molecule straight unbendable and that is important to the function of cellulose it is structural molecule it has to form certain structure ( stems ) so that the plant cell will be tough it will break whereas in glycogen no its not needed to be in that way monomer glucose anomeric beta β glycosidic bond [β:1 4]. 7 | P a g e Let's imagine that we have a polysaccharide that has an alpha α glycosidic bond followed by beta β glycosidic bond then alpha α the question is Did we classify it homo or a heteropolysaccharide ? Actually, this question is not right you are connecting two things that are different of each other when we say homo or hetero we talk about monomers not the type of glycosidic bond regardless how they are connected to each other ( alpha α or beta β glucose is the same monomer ) and is Homopolysaccharide Chitin Chitin is also a structural polysaccharide that exists in insects it forms the exoskeleton if insects and animals like crabs that why when you crush a cockroach you hear a sound that is the chitin!! Again notice! it is homo or heteropolysaccharide?- Homopolysaccharide what is the name of the monomer N-Acetylglucosamine So when you look at the monomer you will find that it has an amino group and linked to the carbon that is not the anomeric carbon so we call it an amino sugar we don’t call it a glycosides we call it a glycosides when the amino group is linked to the anomeric carbon when we look at the structure we find that the monomer is glucose the hydroxyl group located downward the precursor is glucose since we have amino group attached to carbon number two glucosamine and the amino group is modified by the addition of an acetyl group so this is called an N-Acetylglucosamine and it is a Homopolysaccharide so from which I tell you that this sugar is a structural molecule so immediately you should know that the glycosidic bond is a beta β, not alpha α has to be tough and rigid [β:1 4] 8 | P a g e Chitin Pectin Pectin also exist in the cell wall of plant cells And it is modified whereby you see that we have a sugar acid carbon number six is modified by oxidation so we have a sugar acid or the carboxyl group can be modified be methylation so Is this Homopolysaccharide or Heteropolysaccharide? Heteropolysaccharide linkage as [α:1 4]. 9 | P a g e Are polysaccharides reducing? The question is : Are polysaccharides reducing and The answer is no! even though they are branched and even though you have a terminal of residues it's still not enough to make the whole molecule a reducing molecule so in general, we said that polysaccharides are non-reducing molecules Glycosaminoglycans Glycosaminoglycans have a certain characteristics that they exist as repetitive disaccharide And they are large molecules they are important for forming a certain structure like cartilage for example for supporting certain structure in our body in animals as well. So again Glycosaminoglycans composed of the same two disaccharides repeated many times that’s why they are different than other sugars that we had talked about all, what we talked about are basically repetitions the same monosaccharide maybe with the exception of pectin because we have sugar acid and then methylated sugar acid.
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