Chapter 14 Carbohydrates

14.1 Carbohydrates

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Carbohydrates
Carbohydrates are A major source of energy from our diet. Composed of the elements C, H, and O. Also called saccharides, which means sugars.
Copyright 2007 by Pearson Education, Inc. Publishing as Benjamin Cummings

Carbohydrates
Carbohydrates Are produced by photosynthesis in plants. Such as glucose are synthesized in plants from CO2, H2O, and energy from the sun. Are oxidized in living cells (respiration) to produce CO2, H2O, and energy.
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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

Monosaccharides
Monosaccharides consist of 3 to 6 carbon atoms, typically. A carbonyl group (aldehyde or ketone). Several hydroxyl groups.

Aldoses
Aldoses are monosaccharides With an aldehyde group. With many hydroxyl (OH) groups. triose (3 C atoms) tetrose (4 C atoms) pentose (5 C atoms) hexose (6 C atoms) O CH aldose H COH H COH CH2OH Erythose, an aldotetrose
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Ketoses
Ketoses are monosaccharides With a ketone group. With many hydroxyl (OH) groups. triose (3 C atoms) tetrose (4 C atoms) pentose (5 C atoms) hexose (6 C atoms)
CH2OH C=O ketose H COH H COH HCOH CH2OH
Fructose, a ketohexose
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Learning Check
Identify each as aldo- or keto- and as tetrose, pentose,

or hexose:
O C H H C OH H C OH H C OH H C OH CH2OH

CH2OH C O HO C H H C OH CH2OH

B
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Solution
A. aldohexose B. ketopentose

14.2 Structures of Monosaccharides

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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.

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D and L Notations
In a Fischer projection, the OH 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.

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Examples of D and L Isomers of Monosaccharides

O C H H HO H H
D-glucose

O C H O C H H OH H OH H OH CH2OH
D-ribose

OH H OH OH CH2OH

HO H H HO

H OH OH H CH2OH

L-galactose

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Learning Check
Identify each as the D or L isomer. A. B.
O C H HO HO HO H H H CH2OH H HO O C H OH H CH2OH HO H H

C.
CH2OH O H OH OH CH2OH

__-ribose

__- threose

__- fructose
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Solution
Identify each as the D or L isomer. A. B.
O C H HO HO HO H H H CH2OH H HO O C H OH H CH2OH HO H H

C.
CH2OH O H OH OH CH2OH

L-ribose

L-threose

D-fructose
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D-Glucose
D-glucose is Found in fruits, corn syrup, and honey. An aldohexose with the formula C6H12O6. Known as blood sugar in the body. The monosaccharide in polymers of starch, cellulose, and glycogen.

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Blood Glucose Level

In the body, Glucose has a normal blood level of 70-90 mg/dL. A glucose tolerance test measures blood glucose for several hours after ingesting glucose.

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D-Fructose
D-fructose Is a ketohexose C6H12O6. Is the sweetest carbohydrate. Is found in fruit juices and honey. Converts to glucose in the body.
CH2OH C O HO C H H C OH H C OH CH2OH
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D-Fructose
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D-Galactose
D-galactose is
O C H H C OH HO C H HO C H H C OH CH2OH D-Galactose

An aldohexose C6H12O6. Not found free in nature. Obtained from lactose, a disaccharide. A similar structure to glucose except for the OH on C4.

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Learning Check
Draw the structure and Fischer projection of D-fructose.

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Solution
CH2OH C O HO C H H C OH H C OH CH2OH D-Fructose
H H OH OH CH2OH Fischer projection HO CH2OH C=O H

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14.3 Cyclic Structures of Monosaccharides

CH2OH O OH OH
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OH

OH

Cyclic Structures
Cyclic structures Are the prevalent form of monosaccharides with 5 or 6 carbon atoms.
O O

Form when the hydroxyl group on C-5 reacts with the aldehyde group or ketone group.

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Cyclic Haworth Structures

Stable cyclic hemiacetals form When the C=O group and the OH 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 CH2OH group located above the ring.

CH2OH O

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Drawing the Cyclic Structure for Glucose

STEP 1 Number the carbon chain and turn clockwise to form a linear open chain. H O

C
1

H C OH
2

H
6 5

H OH H
4 3 2 1

HO 3 C H H 4 C OH H 5 C OH
6 CH2OH

O H

HOCH2 C C C C C OH OH H OH

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Cyclic Structure for Glucose

STEP 2 Bend the chain to make a hexagon Bond the C5 O to C1. Place the C6 group above the ring. Write the OH groups on C2 and C4 below the ring. Write the OH group on C3 above the ring. Write a new OH on C1.

CH2OH
6 5 4

O
1

OH

OH
3

OH OH

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Cyclic Structure for Glucose (cont)

STEP 3 The new OH on C1 is drawn Down for the anomer. Up for the anomer.
CH2OH CH2OH

O
OH OH OH OH

OH

O OH

OH OH

-D-glucose

-D-glucose
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Summary of the Formation of Cyclic Glucose

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-D-Glucose and -D-Glucose in Solution

When placed in solution, Cyclic structures open and close. -D-glucose converts to -D-glucose and back. There is only a small amount of open chain.
CH2OH O OH OH

CH2OH O OH
OH

H O C H

CH2OH O OH OH

OH

OH OH

OH

-D-glucose (36%)

D-glucose (open) (trace)

OH -D-glucose (64%)
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Cyclic Structure of Fructose

Fructose Is a ketohexose. Forms a cyclic structure. Reacts the OH on C-5 with the C=O on C-2.
CH2OH C O HO C H H C OH H C OH CH2OH OH CH2OH O OH OH OH CH2OH CH2OH O OH OH CH2OH

D-fructose

-D-fructose

-D-fructose
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Learning Check
Write the cyclic form of -D-galactose

O C H H C OH HO C H HO C H H C OH CH2OH
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Solution

CH2OH OH OH OH O

OH

-D-galactose
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14.4 Chemical Properties of Monosaccharides

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Reducing Sugars
Reducing sugars Are monosaccharides with a carbonyl group that oxidizes to give a carboxylic acid. Undergo reaction with Benedicts reagent (Cu2+) to give the corresponding carboxylic acid. Include the monosaccharides glucose, galactose, and fructose.

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Oxidation of D-Glucose
O C H
Benedicts reagent

O C OH H C OH
[O]

Glucose is oxidized to a carboxylic acid

H C OH HO C H H C OH H C OH CH2OH D-glucose

+ Cu

2+

HO C H H C OH H C OH CH2OH D-gluconic acid

+ Cu2O(s)

Cu+ (reduced form)

Glucose is a reducing sugar

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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

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Learning Check
Write the products of the oxidation and reduction of D-mannose.
O C H HO HO H H H H OH OH CH2OH
D-mannose
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Solution
Write the products of the oxidation and reduction of D-mannose.
O CH2OH HO HO H H H H OH OH CH2OH
D-mannitol

O C OH Oxidation HO HO H H H H OH OH CH2OH
D-mannonic acid
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C H Reduction HO HO H H H H OH OH CH2OH
D-mannose

14.5 Disaccharides

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Important Disaccharides
A disaccharide Consists of two monosaccharides. Monosaccharides Disaccharide Glucose + glucose maltose + H2O Glucose + galactose lactose + H2O Glucose + fructose sucrose + H2O

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Maltose
Maltose is A disaccharide also known as malt sugar. Composed of two D-glucose molecules. Obtained from the hydrolysis of starch. Linked by an -1,4-glycosidic bond formed from the OH on C1 of the first glucose and OH on C4 of the second glucose. Used in cereals, candies, and brewing. Found in both the - and - forms.

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Formation of Maltose

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Lactose
Lactose Is a disaccharide of D-galactose and - or -D-glucose. Contains a -1,4glycosidic bond. Is found in milk and milk products.
-form

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Sucrose
Sucrose or table sugar Is obtained from sugar cane and sugar beets. Consists of -D-glucose and -D-fructose.. Has an ,-1,2-glycosidic bond.

-D-glucose

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-D-fructose

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Learning Check
Write the structures and names of the two monosaccharides that form when sucrose is hydrolyzed.

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Solution

-D-glucose

-D-fructose
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Sweeteners
Sugars and artificial sweeteners Differ in sweetness. Are compared to sucrose (table sugar), which is assigned a value of 100.
TABLE 15.2

60 000

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Learning Check
Identify the monosaccharides in each of the following: A. lactose (1) -D-glucose (2) -D-fructose (3) -D-galactose

B. maltose (1) -D-glucose (2) -D-fructose C. sucrose (1) -D-glucose (2) -D-fructose

(3) -D-galactose

(3) -D-galactose
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Solution
Identify the monosaccharides in each of the following: A. lactose (1) -D-glucose (3) -D-galactose B. maltose (1) -D-glucose C. sucrose (1) -D-glucose

(2) -D-fructose

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14.6 Polysaccharides

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Polysaccharides
Polysaccharides Are polymers of D-glucose. Include amylose and amylopectin, starches made of -D-glucose. Include glycogen (animal starch in muscle), which is made of D-glucose. Include cellulose (plants and wood), which is made of -D-glucose.
CH2OH O OH OH

OH

OH

-D-glucose

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Structures of Amylose and Amylopectin

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Amylose
Amylose is A polymer of -Dglucose molecules. Linked by -1,4 glycosidic bonds. A continuous (unbranched) chain.

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Amylopectin
Amylopectin Is a polymer of -Dglucose molecules. Is a branched-chain polysaccharide. Has -1,4-glycosidic bonds between the glucose units. Has -1,6 bonds to branches.

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Glycogen
Glycogen Is the polysaccharide that stores -D-glucose in muscle. Is similar to amylopectin, but is more highly branched.

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Cellulose
Cellulose Is a polysaccharide of glucose units in unbranched chains. Has -1,4-glycosidic bonds. Cannot be digested by humans because humans cannot break down -1,4glycosidic bonds.
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Learning Check
Identify the polysaccharides and types of glycosidic bonds in each of the following:

A.

B.

C.

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Solution
A. Cellulose
B. Amylose Amylopectin C. Glycogen

-1,4-glycosidic bonds
-1,4-glycosidic bonds -1,4-and -1,6-glycosidic bonds -1,4-and -1,6-glycosidic bonds (more branched than amylopectin)

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