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 Con’t
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
 1890’s
 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 Tollen’s and Benedict’s
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 can’t 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
Cow’s 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 Con’t
Foods can be treated with lactase
Lactacid®
 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 Con’t
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 Con’t
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 bonding…insoluble in water
Cellulose Con’t
Can’t 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