macro mols - carbohydrates lesson
TRANSCRIPT
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PolymerizationCarbohydrates
Macromolecules
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Macromolecules
Macro: largeMacromolecules are built by
combining a number of smaller subunits
Monomer: a single subunitPolymer: larger units made by
covalent bonds between monomers
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Building Macromolecules
A large variety of polymers can be built from a few monomers
Cells can create many different macromolecules from a small number of starting materials by arranging them in different combinations
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Analogy: The Asian Kitchen“Fourteen simple basics, augmented by general pantry staples such as sugar, salt, cornstarch, chicken broth, rice, oil, and black pepper, one can take most fresh ingredients and create a plethora of dishes from every province of China.”
http://www.tigersandstrawberries.com/2007/02/21/staple-ingredients-of-the-chinese-pantry/http://nookandpantry.blogspot.ca/2008/02/chinese-pantry-part-i-what-you-need-to.html
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Analogy: Alphabets
26 letters of the alphabet makes over 125,000 words in the English languagehttp://oxforddictionaries.com/words/how-many-words-are-there-in-the-english-language
4 nitrogen bases, A T C G, in DNA makes up our entire genome
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Metabolism
The process by which macromolecules are built from monomers or disassembled is metabolism
Metabolism: the sum of all chemical reactions that occur in a living organism
Classified into 2 types: Anabolism: reactions that build up
molecules Catabolism: reactions that breakdown
molecules
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Anabolism Reactions
Text page 63, Fig. 5.2a.
Condensation (dehydration synthesis): monomers are covalently linked to make a polymer by removing water
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Catabolism Reactions
Hydrolysis: covalent bonds connecting monomers in a polymer are disassembled by the addition of water
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Macromolecules
Four major classes are: 1. Carbohydrates2. Lipids3. Proteins4. Nucleic acids
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What you need to know…
1. Structure of the basic unit (e.g. monomers) that builds up the macromolecule
2. How macromolecules react to form larger molecules
3. How the larger molecules are broken down into basic units
4. Functions of the molecules in living organisms
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Carbohydrate
Carbo = carbon (C)Hydrate = water (H2O)Carbohydrates are multiples of the
basic formula: CH2OExample: A carbohydrate with 6
carbons CH2O x 6 = C6H12O6 = hexose (e.g.
glucose)
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Monomer: Monosaccharides
Mono = 1Saccharide = sugarRanges from 3 to 7 carbons in lengthMost names for sugars end in –ose
Hexose: glucose, fructose
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Function of Monosaccharide
FUEL: short-term energy storagebuilding materialscellular communication
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Monosaccharide Classification
A. Number of carbons in the backboneTriose: 3C Pentose: 5CHexose: 6C
B. Location of the carbonyl group (-C=O)
Aldose: carbonyl group at the end (aldehyde)
Ketose: carbonyl group in the middle (ketone)
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Fig. 5.3
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Numbering System
Where is carbon 1 in each molecule? Explain how the choice was made.
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Linear and Ring forms In aqueous solutions, hexose sugars
form rings C=O group will react with the OH
group on C5 to form a stable 5 or 6 sided ring structure
Count the number of C, H, O in the ring structure. Are any atoms lost?
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Build the linear molecule. Rearrange the bonds to get the final ring form. Hint: it involves the functional group.
In your notes, draw an arrow to show the 2 atoms in the linear structure that connects to form the ring. Number the carbons in both the linear and ring structures.
Practice: Form Ring Structures
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Forming Ring Structures
Fructose
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Ring forms of hexose sugars
Question: How do you distinguish galactose, mannose and fructose from glucose? Refer to specific carbon numbers.
Glucose Galactose Mannose Fructose
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Glucose Galactose Mannose Fructose
Ring forms of hexose sugars
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Glucose Galactose Mannose Fructose
Carbon 4 – OH is up
Carbon 2 – OH is up
Ring forms of hexose sugars
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Glucose Galactose Mannose Fructose
Carbon 4 – OH is up
Carbon 2 – OH is up
5 sided ring
Ring forms of hexose sugars
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Anomeric Carbon
The C of the C=O group is called an anomeric carbon
Depending if the OH group attaches from the top or bottom, different ring structure is formed.
a-glucose
b-glucose
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Anomeric Carbon
The different orientation of the resulting OH group have different names
Alpha (α) = OH group below ringBeta (β) = OH group above ring
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Saccharide Condensation Reaction
Which functional group(s) participates in this reaction?
What is the name of the new functional group formed (red box)?
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Linkage Naming
To name the linkage:
Identify whether the anomeric carbon in the link is α or β
Number the carbons and determine the 2 that are involved in the linkage
Example: α-1,4 linkage
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non-digestible digestible
Linkage: Anomeric Carbonα and β orientation of the anomeric
carbon result in the formation of different types of bonds in polymers
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Dissaccharide
Di = twoCondensation reaction of 2
monosaccharides forming an ether bond known in carbohydrates as a glycosidic bond
3 dissaccharides that all involve glucose: Maltose = glucose + glucose Lactose = glucose + galactose Sucrose = glucose + fructose
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Dissaccharide: Maltose
Glucose + Glucose = Maltose + H2OProduced in malted products (e.g.
beer)Linkage: α-1,4
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Dissaccharide: Lactose
Glucose + Galactose = Lactose + H2O
the major form of sugar in milkPeople with lactose intolerance lack
the enzyme needed to break down lactose
Linkage: β-1,4
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Dissaccharide: Sucrose
Glucose + Fructose = Sucrose + H2O table sugar the major transport form of sugars in
plantsLinkage: α-1,2
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Reducing Sugars
In a chemical reaction, when the anomeric carbon has an OH group, it is considered a reducing sugar.
All monosaccharides are reducing sugars
Identify the anomeric carbon in each molecule:
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Disaccharides: Reducing? Name the monosaccharides Name the disaccharide Name the linkage Is the disaccharide a reducing sugar?
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Disaccharides: Reducing? Name the monosaccharides Name the disaccharide Name the linkage Is the disaccharide a reducing sugar?
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Disaccharides: Reducing? Name the monosaccharides Name the disaccharide Name the linkage Is the disaccharide a reducing sugar?
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Polysaccharide
Polysaccharides: polymers of monosaccharide (glucose) joined by glycosidic linkages.
Two types of function: Storage: Energy storage macromolecule
that is hydrolyzed as needed. Structural support: Building materials for
the cell.
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Starch
glucose monomers joined by α-1,4 linkages
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Starch
Is made up of two forms that have a helical structure
Amylose: unbranched formAmylopectin: branched form
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Starch
Main chain linkage (both): a-1,4-glycosidic bond
Branch linkage (amylopectin): a-1,6-glycosidic bond
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Starch
Found in plantsstored within chloroplastsa way to store surplus glucoseAnimals can eat plants containing
starch and derive energy from it
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Glycogen
Storage in liver and muscle cells of animals
Glucose polymer with extensive branching
Helical structure
Fig. 5.6b
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Glycogen
Function of branching: allows enzyme easy access to breakdown the more loosely packed molecule into glucose
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Glycogen
Main chain linkage: a-1,4-glycosidic bond
Branch linkage: a-1,6-glycosidic bond
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Cellulose
glucose monomers joined by β-1,4 linkages
has no branching this linkage makes every other
glucose molecule face upside down resulting in a straight chain (non-helical) 3D structure
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Cellulose
Make up the plant cell wallStrength of cellulose from
crosslinks: hydrogen bonds between parallel
strands of cellulose H atoms of OH groups on one strand
form H-bonds with OH groups on other strands.
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Fig. 5.8
Cellulose
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Cellulose
Cellulose is found in cell walls of plants cells Humans: Enzymes that digest starch cannot
hydrolyze the β linkages in cellulose Cows: have symbiotic relationships with
microbes that have enzymes that can digest cellulose.
http://blogs.discovermagazine.com/80beats/files/2011/01/CowBiofuel.jpg http://www.nature.com/nature/journal/v470/n7332/images/470008c-i1.0.jpg
http://www.nature.com/nature/journal/v470/n7332/full/470008c.htmlhttp://blogs.discovermagazine.com/80beats/2011/01/27/to-find-the-future-of-biofuels-punch-a-hole-in-a-cow/
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Chitin
Found in:cell walls of many
fungiexoskeletons of
arthropods (insects, spiders, and crustaceans such as crabs, lobsters and shrimp).
http://academic.brooklyn.cuny.edu/biology/bio4fv/page/chitin.html
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Chitin
Similar in structure to cellulose, except that it contains nitrogen
Linkage: β-1,4 http://www.ceoe.udel.edu/horseshoecrab/research/images/Chitin_molecule2_flat.jpg
http://www.nzetc.org/etexts/Bio14Tuat01/Bio14Tuat01_038a.jpg
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Polysaccharide SummaryFunctio
n Structure Animals Plants
Fuel
Support
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Polysaccharide SummaryFunctio
n Structure Animals Plants
Fuel
helical (a -1,4 ) & mostly branched (a -
1,6 )
Glycogen Starch
Supportstraight,
unbranchedβ-1,4
Chitin(fungi &
arthropods)
Cellulose