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9. Carbohydrates
Chapter 16
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CARBOHYDRATES
Contain C, H, O only
CXH2YOY = CX(H2O)Y
i.e hydrates of carbon
most common names end in '-----ose'
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Carbohydrates
General Structural Features
Usually 5/6 membered rings with C and one O
Many -OH groups water soluble (simple ones )
easily broken down for energy
(already partly 'oxidized')
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From Monosaccharides to Polysaccharides
The root sacchar- comes from the Latin saccharum, "sugar".
A monosaccharide is the smallest molecular unit of a carbohydrate.
Glucose, the prototypical monosaccharide, is the most abundant organic molecule on earth.
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A disaccharide is a molecule formed from a combination of two monosaccharides, eg.
sucrose
A polysaccharide is a molecular chain (maybe branched) of hundreds / thousands of mono-
saccharides, eg. cellulose
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Common Carbohydrates
Carbohydrate Monosaccharides, C6(H2O)6 Glucose (blood sugar, grape sugar, dextrose) C6H12O6 Fructose ( levulose ) C6H12O6
Galactose C6H12O6
Disaccharides, C12(H2O)11 Sucrose (table sugar,beet sugar, cane sugar) C12H22O11
Maltose (malt sugar) C12H22O11
Cellobiose C12H22O11
Lactose (milk sugar ) C12H22O11
Polysaccharides, Cx(H2O)y
Starch Cellulose
Formula
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OH
OH
OOH
OH OH
OH
O
OH OH
OH OH
1
23
4
5
6
1
23
4
5
6
Glucose – a 2,3,4,5,6-pentahydroxy hexanal
C6H12O6 – a(aldo)hexose
open chain cyclic (6 mem. ring = pyran)
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Glucose – single then soluble
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OOHOH
OHOH
OHO
OHOH
OHOH
OHOO
O
+
+ H2O
OOOOO O O* *n
Polysaccharides – the Glycosidic Linkage
monosaccharides glycosidic linkage
starch = 1,4 linkages = cellulose
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STARCHESPlant :
Amylose -straight chain (~200 -D glucose units)
Amylopectin - branched every ~25 units (1000+ -D glucose units)
Dextrins -partial breakdown of amylopectin (food additives , paste , fabric finishes )
Animal :
Glycogen
-branches every~12 units
-short-term energy in body (liver & muscle).
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More Branching = Faster ‘Breakdown’
Amylopectin Glycogen
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Amylose Helical Structure
• Left hand helix (partial)
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Iodine test for Starch
• Helical structure of amylose holds the I3- ion; linear cellulose does not
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Carbohydrates The Most Common Energy Source
Chemical Breakdown / Reaction = Digestion
Complex Dextrins Simple Mono-
acetate(2C) + CO2 + H2O + Energy
NB. can be reversed, ie. glucose glycogen
(glucose)(starch)
H2O H2O H2O
O2
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Complex Dextrins Small Mono-
Starch Breakdown / Digestion
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Energy Sources Instant Blood sugar(glucose): ~1g/L or 20Cal or ~30mins. Short Term Liver/Muscles(glycogen): ~325g or ~6 hrs.
the more muscle, the more glycogenany excess is converted into fat
Long Term Fat(adipose tissue): ~ 20kg or ~35 days
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Nutritional / Dietary Carbohydrates
Starch - the digestible carbohydrate(for humans)
Simple - mono-/disaccharides, eg. sugars Complex -seeds/roots of plants, eg. grains(pasta), corn, potatoes, rice
Recommended - at least 55% of our Caloric intake (10% sugar & 45% complex)N A average - 20% sugar + 25% complex!
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Cellulose - indigestible carbohydrate for humans Soluble(pectins/gums) - fruits(apples), grain husks (oat bran)Insoluble(fiber/bulk/roughage) - potato skins, apple peels, celery, lettuce
Recommended - ~30g/dayNA average - ~15g/day
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What is Dextrose?
Dextrose (Blood sugar) is the form of glucose that rotates the plane of polarized
light in a clockwise direction.
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What is “invert sugar?”
• Hydrolysis of (+)sucrose (table sugar) produces equal amounts of (+)glucose and (-) fructose (levulose).
• But, fructose optical rotation is larger (negatively) than glucose rotation is positively. Hence, the resulting solution is levorotatory (-).
• Thus, start with only (+) then get (-) after hydrolysis-so the net result of hydrolysis is inversion of the direction of the optical rotation
• Honey is mostly invert sugar –ie an equal mixture of glucose and fructose
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O
OHOH
OH
O
O
OH
OH
OH
OH
OH
Sucrose -> Glucose + Fructose (Invert)
sucrose(+66)
D-glucose(+52) (dextrose)
D-fructose(-92)
(levulose)
sucrase (invertase)
+
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OO
OH
OH
OHOH
OOH
OH
OHOH
Maltose – the basic unit of Starch
(down) - linkage
requires maltase (humans > yes)
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O
OH
OH
OHOH
OOH
O
OH
OHOH
Cellobiose – the basic unit of Cellulose
(up) - linkage
requires cellobiase (humans > no)
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Beneficial statistical correlations for colon cancer, obesity, diabetes, heart disease.
Acts as a sponge for water and other substances
Functions as a physical 'cleaner'
Soluble - can help lower cholesterol levels
reduces rate of glucose absorption
Insoluble - fills you up eat less fat
'cleans' folds in intestinal walls
no physical damage to intestinal walls
adsorbs/removes many 'nasties'
Why Dietary Fibre? It's Indigestible!
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Cellulose is a major component of grass, leaves, wood, cotton(produced by photosynthesis).
World Biomass Production = 1011 tons annually
Present: Humans benefit indirectly by allowing ruminants(cows, sheep) to digest cellulose and convert it into protein which we eat.
Human Exploitation of Cellulose
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Enzyme & Substrate: like a Lock & Key
Enzymes are huge protein molecules with intricate but well-defined shapes. They are the catalysts that bring about all the chemical reactions in our bodies. For effective reactivity the molecule must fit into the
convolutions of the shape of the enzyme.
Much like a key must fit the tumblers of a lock.
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Lactose Intolerance
Lactase is the enzyme that specifically breaks the -1,4- linkage of lactose to produce D-galactose and
D-glucose. Infants have a highly active form but
70% of adults have some lactase deficiency.
If lactose is not cleaved in small intestine it passes to the colon and 1) absorbs water or 2) is degraded by
bacteria, resulting in cramps, diarrhea, etc.
About 10% of NA adults permanently lose their lactase compared to 3% of Danes and 97% of Thais.
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O
OH
OH
OHOH
OOH
O
OH
OHOH
Lactose (milk sugar) – a disaccharide
lactase + H2O
D-galactose
D-glucose
4-O-(-D-galactopyranosyl)-D-glucopyranose
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Solving the problem• Buy it!
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Sweetness Index
Substance Relative Sweet Taste
Lactose 0.16 Maltose 0.33 Glucose 0.74 Sucrose 1.00 Fructose 1.73
(NB. Glucose + Fructose = Honey or Invert Sugar)
Aspartame 180 Saccharin 300
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Sucrose : lots of –OH’s: high water solubility
-D-glucopyranosyl- -D-fructofuranoside
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Refined Sugar
NA sugar consumption: ~1kg (1750) (annually/person) ~50 kg(1990)
Per day: 50, 000/365= 136 grams per person/day
world-wide production = >80 million tons (60% from cane; 40% from beets)
Dangers: dumps too much glucose into blood too quickly
all other nutrients(vitamins, minerals) are removed
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Everybody’s Comfort Food !Wow !
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An Informative Label ?! …..Not Likely
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Refined Sugar in some Processed Foods
Food % Sugar Jello ~83 Coffeemate ~65 Shake’N Bake
~50 Salad Dressing ~30 Ketchup ~29 Ice cream ~21 Peaches(in syrup) ~18 Peanut butter ~9 Coca Cola ~9
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Sugar in human blood
• Blood sugar is glucose (dextrose)
• It is the only fuel for the brain and the Central nervous system (CNS) and supplies the E for basal metabolism
• For continuous supply, a concentration of 0.06 to 0.11 weight % is maintained
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Control of Blood Sugar (normal ~100mg/dL)
Too Low
Too High
(<75mg/dL) = hypoglycemia(fainting)
(>150mg/dL) = hyperglycemia/diabetes
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Urine test for diabetes
• Above 0.16 weight % in blood , glucose seeps through the kidneys into the urine
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Diabetes Mellitus
Type I (insulin dependent): ~10% of all diabetics (juvenile onset)
Type II (non-insulin dependent; insulin receptors in cells have become inactivated by excess use of sugar): ~90% of all diabetics (formerly called adult onset but now found in 10-12 year olds!)
NB. Diabetes is: 1) second only to trauma for leg amputation 2) leading cause of blindness in adults over 20 3) leading cause of kidney failure 4) almost triples risk of heart attack or stroke
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Type 1 Diabetes
• Body produces virtually no insulin
• Thus insulin needed for treatment
• Absence of insulin causes uncontrolled lipolysis of fat and severe wasting of body tissues, eventually resulting in death
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Living with Type 2 Diabetes
• Body makes too little insulin or its effect is resisted
• In some cases insulin is needed• sometimes controlled with a reduced sugar
diet• Loss of weight will cause an increase in the
number of insulin receptors, hence improved condition
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Canadians Discover Insulin (1921)
• Frederick Banting and his assistant Charles Best isolated insulin from the pancreas of dogs (canine insulin) and administered it to Type 1 patients
• Nobel Prize awarded to Banting and McLeod for this work
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Structural Differences
• Porcine & canine insulin are identical and have 50/51 amino acids in common with human insulin
• Bovine insulin and human insulin have 48/51 amino acids in common
• Thus porcine insulin most often used
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Source of Human Insulin
• Patients who are allergic to these can now get cloned Insulin marketed as the Drug Humulin
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Synthesis of Human Insulin
• Saran Narang (NRC Ottawa) 1930-2007
• Synthesised the proinsulin gene
• Enabled mass production of Humulin
• Via recombinant DNA
• Insulin is a protein
• 51 amino acids
• DNA>RNA>protein
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Other molecules with sugar type structures
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Fake Fats
• Simplesse - from egg white or milk proteins Emulsified starch - in Hellman’s light mayonaisse Emulsified protein - gelatin + water Olestra* ($200 million, by Proctor&Gamble) -may cause cramps/diarrhea(dehydration)
reduces absorption of vit. A, D, E, K (fat- soluble vitamins) into body
* not digested; available in USA since 1996;
must carry warning label; not legal in Canada
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O
OHOH
OH
O
O
OH
OH
OH
OH
OH
Olestra = Sucrose Octa Palmitate
Not OH but OR (R = O=C-C16 (sat. = palmitate)
NB. At least 6OHs esterified to be non-metabolized
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Olestra a Triglyceride
Olestra – Indigestible !
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Chitin (an exoskeleton polymer)
NH
CH3
O
NH
CH3
O
OO
O
OH
OH
OO
OH
OH
*
*n
O
OH
OH
OH
NH2OH
(D)-glucosamine
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Glucosamine
• A simple amino sugar C6H13NO5.
• Produced commercially by hydrolysis of crustacean exoskeletons
• Used in treatment of osteoarthritis
• Sold as a salt-either HCl or sulfate
• Typical dose up to 1.5gr/day
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Glucosamine (3-aminoglucose)
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Blood Typing by Glycoprotein Antigens
Type A: acetylgalactosamine-galactose-acetylglucosamine-PRO
Type B: lactose-galactose-acetylglucosamine-PRO
Type O: galactose-acetylglucosamine-PRO
fucose
fucose
fucose
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Chocolate - Covered Cherries
Chemistry is Everywhere !
Cherries are first coated with sugar paste(sucrose) + sucrase(enzyme). After hardening they are dipped in chocolate and stored. After 1-2 weeks the sucrose is hydrolyzed/split by the sucrase into glucose + fructose which dissolves easily in the cherry juice.
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3 Cherry Blossom Questions
• One ingredient is called “invertase” .What is another name for this?
• Another ingredient is soy lecithin. What function does it serve?
• Another ingredient is “modified vegetable oil” How has it been modified?
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Problem set #3
• Chapt 13 #1
• Chapt 15#1,8,9,10,11,25,29
• Chapt 16#1,9,11,12,18