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Structure and Chemistry 2 Structure and Chemistry Carbohydrates: Structure and Function (BI3.1) Introduction Disaccharides Disaccharides are major energy supplying nutrients in diet Carbohydrates are polyhydroxy aldehydes or ketone with a namely, maltose, lactose, and sucrose. They contain two general formula Cn(H O)n (Fig. 2.1). 2 monosaccharide units attached to one another through glycosidic bonds that are formed between hydroxyl groups of one monosaccharide unit in the polymer with elimination Classification of Carbohydrates of water. Carbohydrates are classified as monosaccharides, disaccha­ Glycosidic Bond rides, oligosaccharides, and polysaccharides (Table 2.1). Bond connecting anomeric carbon to alcohol oxygen is termed as glycosidic bond. O-glycosidic bonds are formed when anomeric carbon is linked via an oxygen atom to Monosaccharides another molecule. N-glycosidic bond is formed between anomeric carbon and an Monosaccharides are simplest form of carbohydrates and amine (or a nitrogen atom), e.g., D-ribose is linked to purine they are aldehydes (aldose) or ketone (ketose) derivative and pyrimidine in nucleic acids. of polyhydric alcohols with at least three carbon atoms. Monosaccharides have a general (CH2O)n (where n ≥ 3). Based on the number of carbon atoms, monosaccharides can Oligosaccharides be as mentioned below: Oligosaccharides are classified into subclasses based on the ••Triose with three carbons. number of monosaccharide molecules that form when one ••Tetrose with four carbons. molecule of the oligosaccharide is hydrolyzed. Examples of ••Pentose with five carbons. oligosaccharides are listed below. •• ••Hexose with six carbons. Fructo­oligosaccharides (FOS) or oligofructose (Jerusalem artichokes, onions, canned foods). ••Galacto­oligosaccharides (GOS): raffinose, stachyose and verbascose (in beans, peas, lentils, cabbage, whole grains), soybean oligosaccharides in soy, and trans­ Synthesis of Major source of galactooligosaccharides (TOS). glycoproteins that are energy for brain •• important components Gluco­oligosaccharides (produced from sucrose). and RBCs of cell membrane ••Human milk oligosaccharides (HMO) (human breast milk). ••Isomalto­oligosaccharides or IOS (produced from Stored as Why we need Cell signaling starch). glycogen carbohydrates? ••Lactosucrose (produced from lactose and sucrose). ••Maltotriose (produced from starch during digestion, Synthesis of found in liquid glucose, brown rice syrup). Synthesis of glycolipids: mucopolysaccharides: water receptor sites binding, lubrication, shock Polysaccharides absorbing property They contain 10 or more monosaccharide units attached Fig. 2.1 Biological significance of carbohydrates. through glycosidic bonds, for examples, starch and 22 Chapter 2 Table 2.1 Classification of carbohydrates Structure and examples Class Subclass Dietary source Aldose Ketose Monosaccharide Triose Glycerol Dihydroxyacetone – Tetrose Erythrose Erythrulose Pentose Ribose Ribulose Hexose Glucose Fructose Disaccharide (composed of Maltose Two glucose units α1 → 4 glycosidic bond Malt liquor two monosaccharide) Sucrose αD-glucose + β-D-fructose α1 → β2 bond Cane sugar Lactose αD-glucose + βD-galactose1 → β4 bond Milk Oligosaccharide (composed Maltotriose Maltose and α1 → 6 glucose Beans of 2–10 monosaccharide Raffinose: Pea bran units, O-linked attached to trisaccharide- Whole grains OH group), e.g., IgA N-linked containing: (attached to protein via glucose, galactose, N-glycosidic bond, e.g., and fructose Aspartate side chain), e.g., dolichol phosphate Polysaccharide (10 or more – Amylose: Potato monosaccharide unit) and α1 → 4 bond, 200–20,000 glucose units highly Tubers their derivatives branched Cereal Homopolysaccharidesa Amylopectin: Grains (α-D glucose) 1 → 4 linkage plus α1 → 6 Legumes branching after 24–30 monomers Homopolysaccharide: Contains only one kind of monosaccharides Starch α1 → 4 linkage and α1 → 6 branching and Glycogen 12–14 monomers of D-glucose α1 → 4 linkage and α1 → 6 branching Cellulose βD-glucose Similar to β1 → 4 bond amylopectin, branches more frequently Insulin βD-fructose (β2 → 1 bond) Plants Dextranb αD-glucose linked at α1 → 6 bond, with Tubers few branches aHeteropolysaccharides will be discussed under separate section. bDextran: Break down product of starch; Limit dextrin: Formed when hydrolysis of starch reaches a branch point. glycogen. Polysaccharides can be linear or branched Table 2.2 Comparison of amylose and amylopectin polymers. Most starch forms in nature are 30% α­amylose and 70 to 90% amylopectin (Table 2.2) and are classified Amylose Amylopectin as homopolysaccharides or heteropolysaccharides. Common monosaccharide constituents of polysaccharides Glycosidic bond: α1–4 α1–4; α1–6 (at branch point) are D­glucose (most common), D­fructose, D­galactose, Linear Branched L­galactose, D­mannose, L­arabinose, and D­xylose Contains several thousand Branching occurs every 24–30 (Table 2.3). Functions of polysaccharides are as follows: glucose residues glucose residue ••Structural. No branching Contains up to 106 glucose residues ••Water binding. Structure and Chemistry 23 Table 2.3 Common monosaccharide derivatives Structure of Monosaccharides of polysaccharides Amino sugar D-glucosamine All monosaccharides are optically active due to the presence of at least one asymmetric carbon. D-galactosamine Sugar derivatives N-acetylneuraminic acid Asymmetric Carbon Sugar acid Glucuronic acid Iduronic acid The carbon atom bonded to four different atoms or groups of atoms is termed as asymmetric carbon or chiral carbon. Glyceraldehyde is the simplest monosachharide having one ••Reserve or storage. asymmetric carbon. ••Cell attachment and recognition sites. ••Generate metabolic intermediates: Isomerism {•Glucose­6­phosphate. Monosaccharide can rotate plane polarized light to right {•Fructose­6­phosphate. (dextrorotatory) or left (levorotatory). ••Biosynthesis of fatty acids (FA) and amino acids. D­ and L­stereo isomers are based on the position of hydroxyl group on asymmetric carbon. Presence of asymmetric carbon Heteropolysaccharides allows the formation of isomers, and the number of isomers of a compound depends on the number of asymmetric They are composed of repeating units of more than one kind carbon atoms (n). of monosaccharides (Box 2.1). Number of isomers = 2n. For example, glucose has four asymmetric carbon atoms, thus 24 = 16 isomers. Box 2.1 Examples of heteropolysaccharides Mucopolysaccharides Mucoprotein Epimer (Glycosaminoglycans) (Glycoprotein) Hyaluronic acid Sialic acid Epimers differ in position of –OH group at 1 or in more asymmetric carbon. D­glucose and D­galactose are epimers Chondroitin sulfate Neuraminic acid of each other at C­4. Similarly, D­mannose and D­glucose are Dermatan sulfate Gangliosides epimers at C­2 (Table 2.8). Keratan sulfate Anomer Heparin sulfate New carbon formed during cyclization is anomeric carbon. This carbon becomes chiral center with two possible Glycosaminoglycan configurations: in β­anomer, –OH group of anomeric carbon is above the plane of ring, and in α­anomer, it is opposite They are linear chains of repeating disaccharides in which as during hemiacetal and hemiketal formation (e.g., C in one of the monosaccharide unit is amino sugar, and one 1 glucose). (or both) of monosaccharide unit contains sulfate or carboxylate group. Glycosaminoglycan (GAG) is present Depending on the size of ring formed, structure is designated; in extracellular matrix, cartilage, tendon, skin, and blood pyranose, if it is six­membered ring and furanose, if it is five­ vessels. The collagen and other proteins are embedded in a membered ring. A six­membered ring structure can adopt gel­like matrix, which is composed of GAG, proteoglycans, either a chair or boat configuration. and glycoproteins (Tables 2.4 and 2.5). Two anomers of glucose have different physical and chemical properties. They are freely interconvertible in aqueous solutions, so at equilibrium, D­glucose is a mixture Carbohydrate Derivatives (or Modified of β­anomer (63.6%) and α­anomer (36.4%). Monosaccharides) D­glucose adopts a chair conformation. Cyclic form of glucose and fructose with five­ and six­membered rings are known Monosaccharides can be converted to several derivatives as glucofuranose and glucopyranose and fructofuranose and (Table 2.6). fructopyranose, respectively. Blood Group Antigens Blood group antigens are proteins or oligosaccharides Structure of Carbohydrates that differ from one individual to another. They consist of α-2-fucosylated galactose substitute with 3-N-acetyl galactosamine (A) or galactose (B) (Table 2.7). Carbohydrates can be depicted as straight chain and ring forms. Straight chain (Fischer projection) form is 24 Chapter 2 Table 2.4 Composition and functions of GAG GAG Repeating unit Tissue distribution Function Feature Hyaluronic acid GlcUA and GlcNAc Synovial fluid Vitreous body: eye Serve as shock absorber β1 → 3 cartilage and lubricant GlcUA GlcNAc Loose connective tissue β1 → 4 GlcUA Vitreous humor form Consists of up to 25,000 clear, viscous jelly like disaccharide, molecular consistency weight up to 107 Chondroitin GlcUA Cartilage To maintain structure located at the site GalNAC and function of tissues of calcification in endochondral bone Dermatan sulfate IdUA, GalNAc Skin, valves blood Sclera: maintain shape Contribute to elasticity β1 → 3 vessels lung, sclera of eye ball of skin IdUA GalNAc Keratin sulfate GlcNAc, Gal Cornea Corneal transparency Present in bone, No uronic acid Bone, cartilage, horny cartilage horny structures, hair,
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