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Carbohydrates

Topics Covered in this Module Diversity of Structure and Function in Carbohydrate Molecules Polysaccharides Major Objectives of this Module Classify monosaccharides based on molecular characteristics. Relate structures of polysaccharides to their functions in cells and organisms. Understand how monosaccharides are classified based on molecular characteristics. Explain how a glycosidic linkage forms by a dehydration synthesis reaction. Classify monosaccharides based on molecular characteristics. Relate structures of polysaccharides to their functions in cells and organisms. Understand how monosaccharides are classified based on molecular characteristics. Explain how a glycosidic linkage forms by a dehydration synthesis reaction.

Macromolecules are Polymers


Polymer - A high molecular weight compound consisting of long chains that may be open, closed, linear, branched, or cross-linked. The chains are composed of repeating units, called monomers, which may be identical or different.

Polymerization is a dehydration reaction: monomer in, water out


HO
Monomer

HO

HO

Monomer

+ H OH Water

Depolymerization is a hydrolysis reaction: water in, monomer out


H OH Water
HO
Monomer

HO

H + HO
Monomer

Classification of Carbohydrates
Carbohydrates are commonly classified on the basis of their size. Monosaccharides Disaccharides (2)

Oligosaccharides (3-10)
Polysaccharides (many) Carbohydrate = carbon hydrate or hydrated carbon atoms. One carbonyl (C=O), many hydroxyls.

LE 5-3
Triose sugars (C3H6O3) Pentose sugars (C5H10O5) Hexose sugars (8 types) (C6H12O6)

Glyceraldehyde

Ps

Ribose Glucose Galactose

Aldehyde: carbonyl carbon (C=O) is terminal

Dihydroxyacetone

Ribulose

Ketone: carbonyl carbon (C=O) is internal

Fructose

Figure 1c

General empirical formula for carbohydrates = (CH2O)n.

Figure 1d

Figure 2

In the ring form of glucose, the carbonyl group, on carbon #1, becomes a hydroxyl group, which exists in one of two possible orientations.

Figure 5

Disaccharides form by dehydration synthesis. The covalent bond is called a glycosidic linkage, the #s refer to the carbons involved.

Polysaccharides
Polysaccharides, the polymers of sugars, can be either structural molecules (cellulose) or energy storage molecules (amylose, amylopectin, glycogen) The structure and function of a polysaccharide are determined by its sugar monomers and the positions of glycosidic linkages

Energy Storage Polysaccharides


Amylose - The form of starch that is composed of long, (thousands) unbranched chains of glucose units which are joined by means of (1-4) glycosidic bonds. Amylopectin - The form of starch that is composed of long, branched chains of glucose units which are joined by means of (1-4) and (16) glycosidic bonds. Branching =~ 1 in every 30 monomers. Glycogen - A highly branched homopolysaccharide of D-glucose units that is the major form of storage of carbohydrate in animals (ie in liver and muscle); the glucose units are linked by means of (1-4) and (1-6) glycosidic bonds. Branching =~ 1 in every 10 monomers

Figure 10b

Figure 10c

Figure 7

Glycogen granules in mouse liver, starch granules in plant chloroplast. Glycogen and starch are energy storage polysaccharides composed of glucose

Structural Polysaccharides: Cellulose


Branch-free linear structure. Linear chain of several hundreds or thousands of beta glucose monomers. Allow hydrogen bonding to occur between adjacent cellulose molecules. Result in strong, parallel groupings of molecules called microfibrils. May be the most abundant organic compound on Earth. Primary component of tough walls that enclose plant cells.

Figure 10a

Enzymes that digest starch by hydrolyzing alpha linkages cant hydrolyze beta linkages in cellulose Cellulose in human food passes through the digestive tract as insoluble fiber Some microbes use enzymes to digest cellulose Many herbivores, from cows to termites, have symbiotic relationships with these microbes

Summary OBJECTIVE Classify monosaccharides based on molecular characteristics. Carbohydrates are organic compounds that include a carbonyl group and several hydroxyl groups. Based on their number of constituent monomers, carbohydrates are classified into monosaccharides, disaccharides, oligosaccharides, and polysaccharides. Monosaccharides are further classified based on three main characteristics, including the location of their carbonyl group the length of their carbon skeleton, which is most often between three and seven carbon atoms the spatial arrangement of hydroxyl groups around asymmetric carbons OBJECTIVE Explain how a glycosidic linkage forms by a dehydration synthesis reaction. Glycosidic linkages form through dehydration synthesis reactions, which have a water molecule as a by-product. In this type of reaction, two monosaccharides form a covalent bond by giving up a water molecule and result in a disaccharide. This process can continue when many monosaccharides polymerize to form polysaccharides. The covalent bond formed between two monosaccharides is called a glycosidic linkage. The type of constituent monomers and the glycosidic bonds that make up the structure dictate the structure and function of polysaccharides.

OBJECTIVE Relate structures of polysaccharides to their functions in cells and organisms. Organisms use a diversity of polysaccharides for energy storage, structural support, cellular identity purposes, and synthesis of other molecules. The most common polysaccharides include starch, glycogen, cellulose, chitin, and peptidoglycan. Carbohydrates have important functions in cells. These functions are related to the structures of the associated molecules. Starch and glycogen serve as energy-storage molecules in plants and animals, respectively. These molecules are composed of glucose monomers joined by 14 glycosidic linkages. The alpha () form of the glucose monomers makes these polysaccharides relatively accessible for energy supply. Cellulose, chitin, and peptidoglycan provide structural support to various organisms. These macromolecules include monosaccharides joined by 14 glycosidic linkages, which makes them more difficult to degrade. Oligosaccharides, unique combinations of about 210 monosaccharides, are located on cell-surface glycoproteins. They function to communicate a cells type or species.