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MacromolecMacromoleculesules

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Organic Compounds

• CompoundsCompounds that contain CARBONCARBON are called organicorganic.

• MacromoleculesMacromolecules are large organic moleculesorganic molecules.

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Carbon (C)Carbon (C)• CarbonCarbon has 4 4

electronselectrons in outer shell.

• CarbonCarbon can form covalent bondscovalent bonds with as many as 4 4 other atoms (elements).

• Usually with C, H, O C, H, O or Nor N.

• Example:Example:CHCH44(methane)(methane)

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MacromoleculesMacromolecules

• Large organic molecules.Large organic molecules.• Also called POLYMERSPOLYMERS.• Made up of smaller “building

blocks” called MONOMERSMONOMERS.• Examples:Examples:

1. Carbohydrates1. Carbohydrates2. Lipids2. Lipids3. Proteins3. Proteins4. Nucleic acids (DNA and RNA)4. Nucleic acids (DNA and RNA)

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Four types of organic compounds

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Question:Question:How Are How Are

MacromolecMacromolecules ules

Formed?Formed?

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Answer:Answer: Dehydration Dehydration SynthesisSynthesis

• Also called “condensation “condensation reaction”reaction”

• Forms polymerspolymers by combining monomersmonomers by “removing “removing water”water”.

HO H

HO HO HH

H2O

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Question:Question: How are How are

Macromolecules Macromolecules separated or separated or

digested?digested?

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Answer: Answer: HydrolysisHydrolysis

•Separates monomersmonomers by “adding water”“adding water”

HO HO HH

HO H

H2O

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In digestion, polymers are broken down into

monomers

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CarbohydratCarbohydrateses

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Characteristics of Carbohydrates

• Consist of carbon, hydrogen, & oxygen• Energy containing molecules• Some provide structure• Basic building block is a monosaccharide

(CH2O)n ; n = 3,5,6

• Two monosaccharides form a disaccharide

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CarbohydratesCarbohydrates

• Small sugar moleculesSmall sugar molecules to large sugar moleculeslarge sugar molecules.

• Examples:Examples:A.A. monosaccharidemonosaccharideB.B. disaccharidedisaccharideC.C. polysaccharidepolysaccharide

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CarbohydratesCarbohydratesMonosaccharide: one sugar Monosaccharide: one sugar

unitunit

Examples:Examples: glucose (glucose (C6H12O6)

deoxyribosedeoxyribose

riboseribose

FructoseFructose

GalactoseGalactose

glucoseglucose

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CarbohydratesCarbohydratesDisaccharide: two sugar unitDisaccharide: two sugar unit

Examples: Examples: – Sucrose (glucose+fructose)Sucrose (glucose+fructose)– Lactose (glucose+galactose)Lactose (glucose+galactose)– Maltose (glucose+glucose)Maltose (glucose+glucose)

glucoseglucoseglucoseglucose

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Hydrolysis of a Disaccharide

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CarbohydratesCarbohydratesPolysaccharide: many sugar Polysaccharide: many sugar

unitsunits

Examples:Examples: starch (bread, starch (bread, potatoes)potatoes)

glycogen (muscle)glycogen (muscle)

cellulose (lettuce, cellulose (lettuce, corn)corn)

glucoseglucoseglucoseglucose

glucoseglucoseglucoseglucose

glucoseglucoseglucoseglucose

glucoseglucoseglucoseglucose

cellulosecellulose

23http://www.chemistryland.com/ElementarySchool/BuildingBlocks/BuildingOrganic.htm

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Important Polysaccharides: Starch

• Consists of glucose subunits• Plants store energy as starch (potatoes,

grains, legumes)• Similar to glycogen in animals• Starch and glycogen can be digested by

animals.

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Glycogen: -molecule for storing excess glucose in humans and animals. -stored in the body predominantly in the liver and the skeletal muscles.

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Why did the potato cross the road?

Because he saw the fork up ahead. Ouch!

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Cellulose

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Important Polysaccharides:

Cellulose• Polymer composed of glucose subunits• Different bond formed than starch• Structural component cell walls) in plants:

wood, paper, cotton• Cannot be digested by animals

glucoseglucoseglucoseglucose

glucoseglucoseglucoseglucose

glucoseglucoseglucoseglucose

glucoseglucoseglucoseglucose

cellulosecellulose

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LIPIDS

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LipidsLipidsExamples:Examples:

1. 1. Fats Fats (triglycerides)(triglycerides)2. Phospholipids2. Phospholipids3. Oils3. Oils4. Waxes4. Waxes5. Steroid 5. Steroid hormoneshormones6. Triglycerides6. Triglycerides

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LipidsLipidsSix functions of lipids:Six functions of lipids:

1.1. Long term energy storageLong term energy storage2.2. Protection against heat loss Protection against heat loss (insulation)(insulation)3.3. Protection against physical shockProtection against physical shock4.4. Protection against water lossProtection against water loss5.5. Chemical messengers (hormones)Chemical messengers (hormones)6.6. Major component of membranes Major component of membranes

(phospholipids)(phospholipids)

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Lipid structure: glycerol + 3 fatty acids

Composed of Carbon, Hydrogen, and OxygenGreater than 2:1 ratio of H:O

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LipidsLipidsTriglycerides:

composed of 1 glycerol1 glycerol and 3 3 fatty acidsfatty acids.

H

H-C----O

H-C----O

H-C----O

H

glycerol

O

C-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH3

=

fatty acids

O

C-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH3

=

O

C-CH2-CH2-CH2-CH =CH-CH2 -CH

2 -CH2 -CH

2 -CH3

=

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Synthesis of a Fat

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Glycerol

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Fatty Acid Structure

•Carboxyl group (COOH) forms the acid.•“R” group is a hydrocarbon chain.

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A Representative Fatty Acid

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Fatty AcidsFatty AcidsThere are two kinds of fatty acidsfatty acids you may see these on

food labels:

1.1. Saturated fatty acids:Saturated fatty acids: no double bonds (bad) no double bonds (bad)

2.2. Unsaturated fatty acids:Unsaturated fatty acids: double bonds (good) double bonds (good)O

C-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH3

=

saturatedsaturated

O

C-CH2-CH2-CH2-CH=CH-CH2 -CH

2 -CH2 -CH

2 -CH3

=

unsaturated

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SaturatedFatty Acid

UnsaturatedFatty Acid

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A Phospholipid

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Phospholipids

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Proteins: Proteins: the body’s the body’s

worker worker moleculesmolecules

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Proteins are like long necklaces with differently shaped beads. Each "bead" is a small molecule called an amino acid. There are 20 standard amino acids, each with its own shape, size, and properties.Proteins typically contain from 50 to 2,000 amino acids hooked end-to-end in many combinations. Each protein has its own sequence of amino acids. Proteins are made of amino acids hooked end-to-end like beads on a necklace.

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Proteins: polymers of amino acids

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Amino acids• C, H, O, and N• Basic builiding

block of proteins• 20 different aas• “R” group gives

identity• All have amino

groups and carboxyl groups

• Amino acids form polypeptide chains, joined by peptide bonds

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FUNCTIONS OF PROTEINS

EXAMPLES

1. structure 1. Keratin (hair) and collagen (ligaments, tendons, skin)

2. transport 2. Hemoglobin, membrane channels

3. movement 3. Actin and myosin (muscle fibers)

4. Control chemical reactions

4. Enzymes

5. Chemical messengers 5. hormones, receptor molecules

6. Immune system 6. Antibodies

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AMINO ACIDS

Jo

??? O

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Formation of a Dipeptide

Dehydration synthesis

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Amino Acid + Amino Acid --> Dipeptide

Amino Acid + Dipeptide --> Tripeptide

A.A. + A.A. + …..+ Tripeptide --> Polypeptide

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Proteins Proteins (Polypeptides)(Polypeptides)

Four levels of protein Four levels of protein structure:structure:

A.A. Primary StructurePrimary Structure

B.B. Secondary Structure Secondary Structure

C.C. Tertiary Structure Tertiary Structure

D.D. Quaternary Structure Quaternary Structure

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Primary StructureAmino acids bonded

together by peptide peptide bonds (straight chains)bonds (straight chains)

aa1 aa2 aa3 aa4 aa5 aa6

Peptide Bonds

Amino Acids (aa)

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To become active, proteins must twist and fold into their

final, or "native," “conformation."

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Secondary StructureSecondary Structure

• 3-dimensional folding arrangement of a primary primary structurestructure into coilscoils and pleatspleats held together by hydrogen bondshydrogen bonds.

• Two examples:Two examples:

Alpha HelixAlpha Helix

Beta Pleated SheetBeta Pleated Sheet

Hydrogen BondsHydrogen Bonds

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Tertiary StructureTertiary Structure• Secondary structuresSecondary structures bentbent and

foldedfolded into a more complex 3-D more complex 3-D arrangementarrangement of linked polypeptides

• Bonds: H-bonds, ionic, disulfide Bonds: H-bonds, ionic, disulfide bridges (S-S)bridges (S-S)

• Call a “subunit”.“subunit”.

Alpha HelixAlpha Helix

Beta Pleated SheetBeta Pleated Sheet

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Quaternary Quaternary StructureStructure

•Composed of 2 or more “subunits”•Globular in shape•Form in Aqueous environments•Example: enzymes (hemoglobin)enzymes (hemoglobin)

subunitssubunits

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How heat denatures a protein

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Provocative Proteins (several hundred thousand different proteins in our body) Spider webs and silk fibers are made of the strong, pliable protein fibroin. Spider silk is stronger than a steel rod of the same diameter, yet it is much more elastic, so scientists hope to use it for products as diverse as bulletproof vests and artificial joints.

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The light of fireflies (also called lightning bugs) is made possible by a protein called luciferase. Although most predators stay away from the bittertasting insects, some frogs eat so many fireflies that they glow!

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The deadly venoms of cobras, scorpions, and puffer fish contain small proteins that act as nerve toxins. Some sea snails stun their prey (and occasionally, unlucky humans) with up to 50 such toxins. One of these toxins has been developed into a drug called Prialt®, which is used to treat severe pain that is unresponsive even to morphine.

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Sometimes ships in the northwest Pacific Ocean leave a trail of eerie green light. The light is produced by a protein in jellyfish when the creatures are jostled by ships. Because the trail traces the path of ships at night, this green fluorescent protein has interested the Navy for many years.

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If a recipe calls for rhino horn, ibis feathers, and porcupine quills, try substituting your own hair or fingernails. It's all the same stuff—alpha-keratin, a tough, water-resistant protein that is also the main component of wool, scales, hooves, tortoise shells, and the outer layer of your skin.

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Nucleic Nucleic AcidsAcids

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Nucleic acids:

polymers of

nucleotides

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What are they made of ?

• Simple units called nucleotides, connected in long chains

• Nucleotides have 3 parts:1- 5-Carbon sugar (pentose)2- Nitrogen containing base

(made of C, H and N)3- A phosphate group ( P )

• The P groups make the links that unite the sugars (hence a “sugar-phosphate backbone”

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What do they do ?Dictate amino-acid sequence in proteinsGive information to chromosomes, which is then passed from parent to offspring

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Nucleic acidsNucleic acids• Two types:Two types:

a. Deoxyribonucleic acid a. Deoxyribonucleic acid (DNA-(DNA- double helix) double helix) b. Ribonucleic acid (RNA-single b. Ribonucleic acid (RNA-single strand) strand)

• Nucleic acids Nucleic acids are composed of long chains of nucleotidesnucleotides linked by dehydration synthesisdehydration synthesis.

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Nucleic acidsNucleic acids• Nucleotides include:Nucleotides include:

phosphate groupphosphate grouppentose sugar (5-carbon)pentose sugar (5-carbon)nitrogenous bases:nitrogenous bases:

adenine (A)adenine (A)thymine (T) DNA onlythymine (T) DNA onlyuracil (U) RNA onlyuracil (U) RNA onlycytosine (C)cytosine (C)guanine (G)guanine (G)

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NucleotideNucleotide

OO=P-O O

PhosphatePhosphate GroupGroup

NNitrogenous baseNitrogenous base (A, G, C, or T)(A, G, C, or T)

CH2

O

C1C4

C3 C2

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SugarSugar(deoxyribose)(deoxyribose)

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DNA - double helixDNA - double helix

P

P

P

O

O

O

1

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4

5

5

3

3

5

P

P

PO

O

O

1

2 3

4

5

5

3

5

3

G C

T A

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Review film: compounds of carbon