Presentation on theme: "1 Chapter 17: Carbohydrates. 2 IMPORTANT FUNCTIONS OF CARBOHYDRATES To provide energy through their oxidation To supply carbon for the synthesis of cell."— Presentation transcript:
1 Chapter 17: Carbohydrates
2 IMPORTANT FUNCTIONS OF CARBOHYDRATES To provide energy through their oxidation To supply carbon for the synthesis of cell components To serve as a stored form of chemical energy To form a part of the structural elements of some cells and tissues Biomolecule – a general term referring to organic compounds essential to life Biochemistry – a study of the compounds and processes associated with living organisms
3 CARBOHYDRATES Carbohydrates are polyhydroxy aldehydes or ketones, or substances that yield such compounds upon hydrolysis. Example:
4 CLASSIFICATION OF CARBOHYDRATES Carbohydrates are classified according to size: Monosaccharide – a single polyhydroxy aldehyde or ketone unit Disaccharide – composed of two monosaccharide units Polysaccharide – very long chains of linked monosaccharide units
5 STEREOCHEMISTRY Many carbohydrates exist as enantiomers – stereoisomers that are mirror images.
6 A chiral object cannot be superimposed on its mirror image. A chiral carbon is one that has four different groups attached to it.
7 The presence of a single chiral carbon gives rise to stereoisomerism. If a carbon atom is attached to four different groups, it is chiral. If any two groups are identical, it is not chiral.
8 Compounds can have more than one chiral carbon: The maximum number of stereoisomers is 2 n where n= number of chiral carbon atoms. Therefore, this compound with two chiral carbon atoms has 2 2 or 4 stereoisomers. The compound on the previous slide with four chiral carbon atoms has 2 4 or 16 stereoisomers.
9 FISCHER PROJECTIONS Fischer projections depict three-dimensional shapes for chiral molecules, with the chiral carbon represented by the intersection of two lines.
10 Fischer projections of carbohydrates have the carbonyl (C=O) at the top. It is projecting away from the viewer behind the plane in which it is drawn. The hydroxyl group on the chiral carbon farthest from the C=O group determines whether the carbohydrate is D (OH on right) or L (OH on left). The two horizontal bonds are coming toward the viewer out of the plane in which they are drawn.
11 D and L enantiomers rotate polarized light in opposite directions.
12 The enantiomer that rotates polarized light to the left is the levorotatory or (-) enantiomer. The enantiomer that rotates it to the right is the dextrorotatory or (+) enantiomer. The D and L designations do not represent dextrorotatory and levorotatory. In some instances only the D or L enantiomers are found in nature. They are rarely found together in the same biological system. For example, humans can only metabolize the D-isomers of monosaccharides.
13 MONOSACCHARIDE CLASSIFICATION Is the monosaccharide an aldehyde (aldose) or ketone (ketose)? How many carbon atoms are in the monosaccharide?
14 COMBINING MONOSACCHARIDE CLASSIFICATIONS
15 PHYSICAL PROPERTIES OF MONOSACCHARIDES Most are called sugars because they taste sweet. Because of the many –OH groups, they form hydrogen bonds with water molecules and are extremely water soluble.
16 MONOSACCHARIDE REACTIONS All monosaccharides with at least five carbon atoms exist predominantly as cyclic hemiacetals and hemiketals. A Haworth structure can be used to depict the (-OH on the anomeric carbon pointing down) and (-OH on the anomeric carbon pointing up) anomers of a monosaccharide. Anomers are stereoisomers that differ in the 3-D arrangement of groups at the anomeric carbon of an acetal, ketal, hemiacetal, or hemiketal group.
17 SIX-MEMBERED PYRANOSE RING SYSTEM
18 FIVE-MEMBERED FURANOSE RING SYSTEM
19 MONOSACCHARIDE REACTIONS, cont. The –OH groups of monosaccharides can behave as alcohols and react with acids (especially phosphoric acid) to form esters.
20 MONOSACCHARIDE REACTIONS, cont. Cyclic monosaccharide hemiacetals and hemiketals react with alcohols to form acetals and ketals, referred to as glycosides.
21 IMPORTANT MONOSACCHARIDES Ribose and Deoxyribose Used in the synthesis of DNA and RNA Glucose Most nutritionally important monosaccharide Sometimes called dextrose or blood sugar
22 IMPORTANT MONOSACCHARIDES, cont. Galactose A component of lactose (milk sugar) Fructose The sweetest monosaccharide Sometimes called levulose or fruit sugar
23 DISACCHARIDES Two monosaccharide units linked together by acetal or ketal glycosidic linkages A glycosidic linkage is identified by: the numbers associated with the carbon atoms joined ﾊ together by the linkage the configuration of the linkage for any anomeric carbon atom joined by the linkage
24 IMPORTANT DISACCHARIDES Maltose Two glucose units linked (1 4) Formed during the digestion of starch to glucose Found in germinating grain Hemiacetal means maltose is a reducing sugar
25 IMPORTANT DISACCHARIDES, cont. Lactose Galactose and glucose units linked (1 4) Found in milk Hemiacetal means lactose is a reducing sugar Sucrose Fructose and glucose units Found in many plants (especially sugar cane, sugar beets) Not a reducing sugar
26 POLYSACCHARIDES Starch A polymer consisting of glucose units Has two forms Unbranched amylose (10-20%) Branched amylopectin (80-90%) Amylose complexes with iodine to form a dark blue color
27 THE STRUCTURE OF AMYLOSE The molecular conformation of starch and the starch-iodine complex: (a) the helical conformation of the amylose chain and (b) the starch-iodine complex.
28 AMYLOPECTIN STRUCTURE
29 POLYSACCHARIDES, cont. Glycogen (animal starch) A polymer of glucose units Used to store glucose, especially in the liver and muscles Structurally similar to amylopectin with (1 4) and (1 6) linkages, but more highly branched
30 POLYSACCHARIDES, cont. Cellulose A polymer of glucose units The most important structural polysaccharide Found in plant cell walls Linear polymer like amylose, but has (1 4) glycosidic linkages Not easily digested, a constituent of dietary fiber