Chapter 15 Carbohydrates
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1 Chapter 15 Carbohydrates 15.1 Carbohydrates Copyright 2007 by Pearson Education, Inc. Publishing as Benjamin Cummings 1
2 Carbohydrates Carbohydrates are A major source of energy from our diet. Composed of the elements C,, and. Also called saccharides, which means sugars. Copyright 2007 by Pearson Education, Inc. Publishing as Benjamin Cummings 2
3 Carbohydrates Carbohydrates Are produced by photosynthesis in plants. Such as glucose are synthesized in plants from C 2, 2, and energy from the sun. Are oxidized in living cells (respiration) to produce C 2, 2, and energy. Copyright 2007 by Pearson Education, Inc Publishing as Benjamin Cummings 3
4 Types of Carbohydrates The types of carbohydrates are Monosaccharides, the simplest carbohydrates. Disaccharides, which consist of two monosaccharides. Polysaccharides, which contain many monosaccharides. Copyright 2007 by Pearson Education, Inc. Publishing as Benjamin Cummings 4
5 Monosaccharides Monosaccharides consist of 3 to 6 carbon atoms, typically. A carbonyl group (aldehyde or ketone). Several hydroxyl groups. 5
6 Aldoses Aldoses are monosaccharides With an aldehyde group. With many hydroxyl ( ) groups. triose (3 C atoms) tetrose (4 C atoms) pentose (5 C atoms) hexose (6 C atoms) C aldose C C C 2 Erythose, an aldotetrose 6
7 Ketoses Ketoses are monosaccharides With a ketone group. With many hydroxyl ( ) groups. triose (3 C atoms) tetrose (4 C atoms) pentose (5 C atoms) hexose (6 C atoms) C 2 C= ketose C C C C 2 Fructose, a ketohexose 7
8 Learning Check Identify each as aldo- or keto- and as tetrose, pentose, or hexose: C 2 C C C C C C C C C 2 C 2 A B 8
9 Solution A. aldohexose B. ketopentose 9
10 Chapter 15 Carbohydrates 15.2 Structures of Monosaccharides Copyright 2007 by Pearson Education, Inc. Publishing as Benjamin Cummings 10
11 Fischer Projections A Fischer projection Is used to represent carbohydrates. Places the most oxidized group at the top. Shows chiral carbons as the intersection of vertical and horizontal lines. Copyright 2007 by Pearson Education, Inc Publishing as Benjamin Cummings 11
12 D and L Notations In a Fischer projection, the group on the Chiral carbon farthest from the carbonyl group determines an L or D isomer. Left is assigned the letter L for the L-isomer. Right is assigned the letter D for the D-isomer. Copyright 2007 by Pearson Education, Inc Publishing as Benjamin Cummings 12
13 Examples of D and L Isomers of Monosaccharides C C 2 C C 2 C C 2 D-glucose D-ribose L-galactose 13
14 Learning Check Identify each as the D or L isomer. A. B. C. C C 2 C C 2 C 2 C 2 -ribose - threose - fructose 14
15 Solution Identify each as the D or L isomer. A. B. C. C C 2 C C L-ribose 2 C L-threose 2 D-fructose C 2 15
16 D-Glucose D-glucose is Found in fruits, corn syrup, and honey. An aldohexose with the formula C Known as blood sugar in the body. The monosaccharide in polymers of starch, cellulose, and glycogen. Copyright 2007 by Pearson Education, Inc Publishing as Benjamin Cummings 16
17 Blood Glucose Level In the body, Glucose has a normal blood level of mg/dl. A glucose tolerance test measures blood glucose for several hours after ingesting glucose. Copyright 2007 by Pearson Education, Inc Publishing as Benjamin Cummings 17
18 D-Fructose D-fructose Is a ketohexose C Is the sweetest carbohydrate. Is found in fruit juices and honey. Converts to glucose in the body. Copyright 2007 by Pearson Education, Inc Publishing as Benjamin Cummings C 2 C C C C C 2 D-Fructose 18
19 D-Galactose D-galactose is An aldohexose C Not found free in nature. btained from lactose, a disaccharide. A similar structure to glucose except for the on C4. C C C C C C 2 D-Galactose 19
20 Learning Check Draw the structure and Fischer projection of D-fructose. 20
21 Solution C 2 C C C C C 2 C 2 C= C 2 D-Fructose Fischer projection 21
22 Chapter 15 Carbohydrates 15.3 Cyclic Structures of Monosaccharides C 2 Copyright 2007 by Pearson Education, Inc Publishing as Benjamin Cummings 22
23 Cyclic Structures Cyclic structures Are the prevalent form of monosaccharides with 5 or 6 carbon atoms. Form when the hydroxyl group on C-5 reacts with the aldehyde group or ketone group. 23
24 Cyclic aworth Structures Stable cyclic hemiacetals form When the C= group and the are part of the same molecule. For hexoses, the hydroxyl group on C-5 reacts with the aldehyde group or ketone group. The cyclic structure of a D-isomer has the last C 2 group located above the ring. C 2 24
25 Drawing the Cyclic Structure for Glucose STEP 1 Number the carbon chain and turn clockwise to form a linear open chain C C C C C C 2 C 2 C C C C C 25
26 Cyclic Structure for Glucose STEP 2 Bend the chain to make a hexagon Bond the C5 to C1. Place the C6 group above the ring. Write the groups on C2 and C4 below the ring. Write the group on C3 above the ring. Write a new on C1. C
27 Cyclic Structure for Glucose (cont) STEP 3 The new on C1 is drawn Down for the α anomer. Up for the β anomer. C 2 C 2 β α α-d-glucose β-d-glucose 27
28 Summary of the Formation of Cyclic Glucose Copyright 2007 by Pearson Education, Inc Publishing as Benjamin Cummings 28
29 α-d-glucose and β-d-glucose in Solution When placed in solution, Cyclic structures open and close. α-d-glucose converts to β-d-glucose and back. There is only a small amount of open chain. C 2 C 2 α-d-glucose D-glucose (open) β-d-glucose (36%) (trace) (64%) C C 2 29
30 Cyclic Structure of Fructose Fructose Is a ketohexose. Forms a cyclic structure. Reacts the on C-5 with the C= on C-2. C 2 C 2 C 2 C 2 C C C C 2 C C 2 D-fructose α-d-fructose β-d-fructose 30
31 Learning Check Write the cyclic form of α-d-galactose C C C C C C 2 31
32 Solution C 2 α-d-galactose 32
33 Chapter 15 Carbohydrates 15.4 Chemical Properties of Monosaccharides Copyright 2007 by Pearson Education, Inc. Publishing as Benjamin Cummings 33
34 Reducing Sugars Reducing sugars Are monosaccharides with a carbonyl group that oxidizes to give a carboxylic acid. Undergo reaction with Benedict s reagent (Cu 2+) to give the corresponding carboxylic acid. Include the monosaccharides glucose, galactose, and fructose. 34
35 xidation of D-Glucose C C C C Benedicts reagent + Cu 2+ [] C C C C Glucose is oxidized to a carboxylic acid + Cu 2 (s) C C 2 C C 2 Cu + (reduced form) D-glucose D-gluconic acid Glucose is a reducing sugar 35
36 Reduction of Monosaccharides The reduction of monosaccharides Involves the carbonyl group. Produces sugar alcohols called alditols. Such as D-glucose gives D-glucitol also called sorbitol. D-Glucitol Copyright 2007 by Pearson Education, Inc. Publishing as Benjamin Cummings 36
37 Learning Check Write the products of the oxidation and reduction of D-mannose. C C 2 D-mannose 37
38 Solution Write the products of the oxidation and reduction of D-mannose. C 2 C C Reduction xidation C 2 C 2 C 2 D-mannitol D-mannose D-mannonic acid 38
39 Chapter 15 Carbohydrates 15.5 Disaccharides Copyright 2007 by Pearson Education, Inc. Publishing as Benjamin Cummings 39
40 Important Disaccharides A disaccharide Consists of two monosaccharides. Monosaccharides Glucose + glucose Glucose + galactose Glucose + fructose Disaccharide maltose + 2 lactose + 2 sucrose
41 Maltose Maltose is A disaccharide also known as malt sugar. Composed of two D-glucose molecules. btained from the hydrolysis of starch. Linked by an α-1,4-glycosidic bond formed from the α on C1 of the first glucose and on C4 of the second glucose. Used in cereals, candies, and brewing. Found in both the α- and β - forms. 41
42 Formation of Maltose Copyright 2007 by Pearson Education, Inc. Publishing as Benjamin Cummings 42
43 Lactose Lactose Is a disaccharide of β- D-galactose and α- or β-d-glucose. Contains a β -1,4- glycosidic bond. Is found in milk and milk products. α-form Copyright 2007 by Pearson Education, Inc. Publishing as Benjamin Cummings 43
44 Sucrose Sucrose or table sugar Is obtained from sugar cane and sugar beets. Consists of α-d-glucose and β-d-fructose.. as an α,β-1,2-glycosidic bond. α-d-glucose Copyright 2007 by Pearson Education, Inc. Publishing as Benjamin Cummings β-d-fructose 44
45 Learning Check Write the structures and names of the two monosaccharides that form when sucrose is hydrolyzed. 45
46 Solution α-d-glucose β-d-fructose 46
47 Sweeteners Sugars and artificial sweeteners Differ in sweetness. Are compared to sucrose (table sugar), which is assigned a value of 100. TABLE
48 Learning Check Identify the monosaccharides in each of the following: A. lactose (1) α-d-glucose (2) β-d-fructose (3) β-d-galactose B. maltose (1) α-d-glucose (2) β-d-fructose (3) β-d-galactose C. sucrose (1) α-d-glucose (2) β-d-fructose (3) β-d-galactose 48
49 Solution Identify the monosaccharides in each of the following: A. lactose (1) α-d-glucose (3) β-d-galactose B. maltose (1) α-d-glucose C. sucrose (1) α-d-glucose (2) β-d-fructose 49
50 Chapter 15 Carbohydrates 15.6 Polysaccharides Copyright 2007 by Pearson Education, Inc. Publishing as Benjamin Cummings 50
51 Polysaccharides Polysaccharides Are polymers of D-glucose. Include amylose and amylopectin, starches made of α-d-glucose. Include glycogen (animal starch in muscle), which is made of α- D-glucose. Include cellulose (plants and wood), which is made of β-d-glucose. C 2 α-d-glucose 51
52 Structures of Amylose and Amylopectin Copyright 2007 by Pearson Education, Inc. Publishing as Benjamin Cummings 52
53 Amylose Amylose is A polymer of α-dglucose molecules. Linked by α-1,4 glycosidic bonds. A continuous (unbranched) chain. Copyright 2007 by Pearson Education, Inc. Publishing as Benjamin Cummings 53
54 Amylopectin Amylopectin Is a polymer of α-dglucose molecules. Is a branched-chain polysaccharide. as α-1,4-glycosidic bonds between the glucose units. as α-1,6 bonds to branches. Copyright 2007 by Pearson Education, Inc. Publishing as Benjamin Cummings 54
55 Glycogen Glycogen Is the polysaccharide that stores α-d-glucose in muscle. Is similar to amylopectin, but is more highly branched. Copyright 2007 by Pearson Education, Inc. Publishing as Benjamin Cummings 55
56 Cellulose Cellulose Is a polysaccharide of glucose units in unbranched chains. as β-1,4-glycosidic bonds. Cannot be digested by humans because humans cannot break down β-1,4- glycosidic bonds. Copyright 2007 by Pearson Education, Inc. Publishing as Benjamin Cummings 56
57 Learning Check Identify the polysaccharides and types of glycosidic bonds in each of the following: A. B. C. 57
58 Solution A. Cellulose β-1,4-glycosidic bonds B. Amylose α-1,4-glycosidic bonds Amylopectin α-1,4-and α-1,6-glycosidic bonds C. Glycogen α-1,4-and α-1,6-glycosidic bonds (more branched than amylopectin) 58
3) How many monosaccharides are connected to each other in a disaccharide? A) 1 B) 2 C) 3 D) 4
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