Ch.

19 Carbohydrates

Milbank High School

Chapter Objectives
1.What are carbohydrates? What is the difference between mono-, di-, and polysaccharides? 2.What are the structures of the most commonly occurring monosaccharides? Be able to classify them as aldoses or ketoses and as trioses, pentoses, or hexoses. 3.What is the difference between a D and an L sugar?

Chapter Objectives
4.What is mutarotation? How does it occur? 5.What are the structures of sucrose, lactose, and maltose, the most common disaccharides? What monosaccharides make up each of these disaccharides? 6.Compare and contrast starch, glycogen, and cellulose.

What is Biochemistry?
The chemistry of molecules and reactions found in living organisms

Carbohydrates
Carbon hydrates Compounds containing carbon, hydrogen, and oxygen
Starches and fibers (complex carbohydrates) Sugars Cellulose

Contain hydroxyl groups

And either an aldehyde or ketone

Known as polyhydroxy aldehydes or ketones

Monosaccharides
Simple carbohydrates
Cannot be further hydrolyzed

Contain 3-7 carbons Readily dissolve in water Can link together to form more complex carbohydrates
Disaccharides Trisaccharides Polysaccharides

Sec. 19.1 General Terminology and Stereochemistry

Named using IUPAC to name monosaccarides Name the number of carbons, then add -ose
Trios, tetrose, pentose, hexose etc

If aldehyde is attached: aldotetrose If ketone is attached: ketotetrose

Common monosaccharides
Glucose Fructose

Enantiomers
Molecules that are nonsuperimposable mirror images of each other Have identical physical properties except one:
They rotate plane-polarized light in opposite directions

Trioses
Simplest sugars Two enantiomers
D

sugars L sugars

Sec. 19.2 Hexoses

Aldohexoses
16 isomers (8 enantiomeric pairs) 3 most common:
Glucose, mannose, galactose

Ketohexoses
8 isomers
fructose

Glucose
Most abundant sugar in nature
Fruits
grape sugar Dextrose b/c it is dextrorotatory

Carbs converted to glucose

Produces energy for our cells Circulating carbohydrate
Blood sugar

Glucose Cont
Synthetically made by the hydrolysis of starch
Corn starch
corn sugar

Mannose
Component of polysaccharide mannan
Berries Vegetable ivory endosperm

Differs from glucose at only one point

Galactose
Needed by human body for synthesis of lactose
In mammary glands

Also important constituent of the glycolipids

Occur in brain in myelin sheath of nerve cells brain sugar Differs from glucose at only one point

Fructose
Only naturally occurring ketohexose Also similar structure to that of glucose Found in honey (40%) Formed in prostate gland
Energy source for spermatozoa

Artificial Sweeteners
High-intensity sweeteners Manufactured in place of mono- and disaccharides Saccharin
1890s 500-700 times sweeter than sucrose Carcinogenic

Artificial Sweeteners
Aspartame
1967 160 times sweeter than sucrose Used in diet soda

Sucralose
1998 600 times sweeter than sucrose Passes through body unchanged

Sec. 19.3 Cyclic Structures of Monosaccharides

Sec. 19.4 Properties of Monosaccharides

Crystalline solids at room temperature Quite soluble in water Converted to anions when Tollens and Benedicts reagents are used Used in simple and rapid diagnostic tests for the presence of glucose in blood or urine

Sec. 19.5 Disaccharides

Composed of two monosaccharide units Joined when one monosaccharide reacts with the hydroxyl group of a second monosaccharide Forms a carbon-oxygen-carbon linkage
glycosidic linkage

Maltose
Occurs in sprouting grain Forms malt in the manufacture of beer
malt sugar

About 30% as sweet as sucrose Body cant utilize it directly Must be broken down by enzymes

Lactose
Milk sugar Occurs in the milk of humans, cows, and other mammals Human milk: 7.5% lactose Cows milk: 4.5% lactose Synthesized only by mammary tissue in nature Commercial produced from whey (from cheese) 1/6th as sweet as sucrose

Lactose Intolerance
People are unable to digest lactose in milk Need lactase in small intestine to digest it properly Up to 20% of US population suffer some degree of lactose intolerance Produces bacteria in colon if not broken down properly
Leads to abdominal distension, cramps, diarrhea

Lactose Intolerance Cont

Foods can be treated with lactase Lactaid
Tablets taken orally with dairy foods to assist in their digestion

Sucrose
Beet sugar, cane sugar, table sugar, or just sugar Largest selling pure organic compound in the world Obtained from sugar canes and beets Average American: 100 pounds of sucrose every year

Sucrose Cont
May cause cancer, heart disease, migraine headaches, hyperactivity in children, obesity, and tooth decay

Sec. 19.6 Polysaccharides

Most abundant carbs in nature Store energy and make up plant cells High-molar mass Starch, glycogen, and cellulose

Starch
Most important source of carbs in the human diet More than 50% of our carb intake Granule form
Storage

Potatoes: 15% Wheat: 55% Corn: 65% Rice: 75%

Starch Cont
Mixture of amylose and amylopectin Amylose: 60-300 glucose units per chain Amylopectin: 300-6000 glucose units Commercial starch
White powder
Stamps, envelopes, labels (sticky upon wetting)

Glycogen
animal starch Reserve carb of animals All mammalian cells contain glycogen
Liver and skeletal cells the most

Used when fasting

Cellulose
Fibrous carb found in all plants Cell walls Most abundant of all carbs Makes up 50% of all carbon in the vegetable world Much hydrogen bondinginsoluble in water

Cellulose Cont
Cant be digested by humans Herbivores contain special enzymes to digest it and use it for energy Termites

Dietary Fiber
Insoluble fiber (cellulose) Reduces risk of colon cancer and heart disease (reduces cholesterol) ADA recommends 20-35 g a day
Most Americans get 14-15 g a day