2 IMPORTANT FUNCTIONS OF CARBOHYDRATES To provide energy through their oxidationTo supply carbon for the synthesis of cell componentsTo serve as a stored form of chemical energyTo form a part of the structural elements of some cells and tissuesBiomolecule – a general term referring to organic compounds essential to lifeBiochemistry – a study of the compounds and processes associated with living organisms
3 CARBOHYDRATESCarbohydrates 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 unitDisaccharide – composed of two monosaccharide unitsPolysaccharide – very long chains of linked monosaccharide units
5 STEREOCHEMISTRYMany 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 2n where n= number of chiral carbon atoms.Therefore, this compound with two chiral carbon atoms has 22 or 4 stereoisomers.The compound on the previous slide with four chiral carbon atoms has 24 or 16 stereoisomers.
9 FISCHER PROJECTIONSFischer 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?
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.
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 RNAGlucose 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 A glycosidic linkage is identified by: Two monosaccharide units linked together by acetal or ketal glycosidic linkagesA glycosidic linkage is identified by:the numbers associated with the carbon atoms joined ﾊ together by the linkagethe configuration of the linkage for any anomeric carbon atom joined by the linkage
24 IMPORTANT DISACCHARIDES Maltose Two glucose units linked (14) 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 (14) Found in milk Hemiacetal means lactose is a reducing sugarSucrose Fructose and glucose units Found in many plants (especially sugar cane, sugar beets) Not a reducing sugar
26 POLYSACCHARIDESStarch A polymer consisting of glucose units Has two formsUnbranched 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.
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 (14) and(16) 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 (14) glycosidic linkages Not easily digested, a constituent of dietary fiber