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Biomolecules: Carbohydrates
Last revised: Friday, June 27, 2003 Copyright 2002. Thomas M. Terry
Reading: Ch. 5 in text
Note: These notes are provided as a guide to topics the
instructor hopes to cover during lecture. Actual coverage will always
differ somewhat from what is printed here. These notes are not a substitute
for the actual lecture!
Monomers& Polymers
Other than water, biomolecules fall into 4 classes:
- proteins
- nucleic acids
- polysaccharides
- lipids
Each class contains small molecules (=
monomers
), joined together to make large molecules (=
polymers
); Only a few types of monomers; billions of different polymers
Condensation Reactions
: involve release of water H2O, joining together of two monomers by covalent bond to form polymer. Occurs in
biosynthesis
.
General formula: A-OH + H-B A-B + H2O
Hydrolysis reactions
: reverse of condensation. Involves adding water to split covalent bond, release of two smaller molecules. Occurs in digestion.
General formula: A-B + H2O A-OH + H-B
Note: A-B could be amino acids, sugars, etc.
View
animation of condensation and hydrolysis
(Campbell website activity)
Structure and Naming of Carbohydrates
- Chemical formula: (CH2O)n, where n= some integer (3 or greater). Examples:
- C3H6O3 - three carbons,
triose
sugar
- C6H12O6 - six carbons,
hexose
sugar
-
monomers
=
sugars
, also called saccharides:
monosaccharides
,
disaccharides
,
trisaccharides
, etc. Beyond 5 or so, called = polysaccharides (often contain 1000's of sugar units)
- Names end in
-ose
(sucrose, glucose, frucose,
ribose, etc.)
- Major distinctive characteristic: every Carbon atom has
H-C-OH
, except one Carbon atom has a carbonyl (C=O) group.
- Some sugars have aldehyde group = aldose sugars (e.g., glucose); other sugars have keto group = ketose sugars (e.g., fructose)
- Review
properties of carbohydrates (Campbell website activity)
- -- 6-Carbon sugars (hexoses) especially.
- Contrast with lipids. Lipid content typically
9 kcal/gram
; sugars only
4.2 kcal/gram
- Presence of -OH groups on sugars decreases energy content, but increases solubility
- Bottom line: fats store more Energy, but are less soluble and hence less rapidly accessible.
- important substrates for building other needed molecules (e.g. amino acids)
- 5-C sugars ribose, deoxyribose are integral parts of RNA, DNA backbone chains
- molecular "tags" on membrane proteins face outside of cell, used for recognition of specific cells and molecules. Proteins with sugar tags are called
glycoproteins
.
- The most abundant sugars are the
hexoses
, with 6 carbons and the structural formula C6H12O6. (Actually, there are also many derivatives of hexoses containing slight modifications. The sugar that makes up lobster shells is built from hexosamine, a 6-carbon sugar with an added amino group).
-
Glucose
: the single most abundant sugar on planet earth
- Glucose is the principal sugar found in human blood, carried throughout the body as a major source of energy for the billions of cells throughout the body. Some cells, such as brain neurons, rely entire lyon glucose as their only energy source, and without a steady supply of glucose they cease functioning. Hence glucose is an extremely important molecule for human metabolism, and its blood concentration is carefully regulated by hormones such as insulin and glucagon. Glucose is also the sugar from which many polysaccharides are built, including cellulose that makes up plant cell walls.
- Sugars can exist in one of two forms:
liner
or
cyclic
(ring). Although we often draw them as linear structures, they quickly fold up into ring shaped molecules in water, as a result of the reaction of their keto or aldehyde groups with a hydroxyl group.
View linear and ring forms of glucose
View linear and ring forms of common sugars (Campbell website activity)
-
Galactose
is an important hexose, found in lactose (milk sugar) along with glucose,and in many plant polysaccharides.
-
Fructose
, also called "fruit sugar", is another important hexose found in many fruits and vegetables. Fructose satisfies the "sweet tooth", tasting twice as sweet as sucrose (table sugar), so can be used in lower amounts, and some food products incorrectly advertise fructose as a "sugar-free" substitute. The switch from sucrose (cane sugar) to fructose (derived from corn) by major soft drink manufacturers caused major problems for the economies of some developing countries whose economies were largely dependent on sugar cane.
- Important 5-C sugars:
ribose
,
deoxyribose
(found in RNA, DNA respectively)
-
sucrose
= glucose-fructose
.
- View diagram showing sucrose assembly
- Found in sugar cane, sugar beets.
- Used to be the major sugar used for sweetening foods, soft drinks, etc.
- Economies of many 3rd world countries were based on supplying sugar.
- But soft drink companies switched to fructose (from corn products, largely from U.S. and Europe) in 1980's, caused tremendous global economic impact, many countries lost trade.
- Need enzyme sucrase to hydrolyze the covalent bond, release glucose and fructose.
View sucrose molecular model
. (This file needs to viewed with the CHIME plug-in. If you can't view this file, see a
stick model of sucrose
instead.)
-
lactose
= glucose-galactose
.
- Found in milk from lactating mammals only.
- Enzyme,
lactase
(also called
galactosidase
), breaks apart the two sugars so they can be separately metabolized.
- All human infants produce enzyme lactase
- Majority of adult humans (especially of Asian, African, Eastern European ancestries) lose ability to hydrolyze this compound, due to genetic inability to produce lactase enzyme as adults. They are
lactose-intolerant
, suffer severe intestinal cramping when lactose is eaten (because bacteria in gut now have access to it, generate gaseous and acid byproducts by fermentation).
-
maltose
=
glucose-glucose
.
- Found in barley, used in beer-making process, also for malted milk drinks.
Review formation of disaccharides (Campbell website activity)
- Polysaccharides (polymers): cell's can't store large concentrations of monosaccharides -- this produces osmotic problems and would cause water to leak out of cells. Instead, convert them into polymers.
View monomer-polymer relation in carbohydrates
-
Glycogen
(found in animals)
-
Starch
(found in plants);
- Both these polymers are branched chain polymers of
glucose
.
- View molecular structure of starch. Glycogen is very similar, slightly more branching.
- Function as energy reserves, soluble, available very quickly.
- Human body stores enough glycogen to provide sugar to blood for 24-36 hours during fasting.
- View stained glycogen (red) in animal liver cells
- View stained starch aggregates (brown) in plant cells
-
Cellulose
(plant woody material, cotton fibers, etc.). Also
lignins
(found as parts of cell walls.)
-
Chitin
- polymer of
glucosamine
(glucose modified by addition of amino groups).
- Makes very rigid polymer, used by insects, crustaceans, and other arthropods as exoskeleton material.
- View molecular structure of chitin
- View lobster shell.
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