Ch 3 PowerPoint Biology 201

Chapter 03

Lecture and Animation Outline

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1

The Chemical BuildingBlocks of Life

Chapter 3

2

3

Carbon

• Framework of biological molecules consists primarily of carbon bonded to – Carbon– O, N, S, P or H

• Can form up to 4 covalent bonds• Hydrocarbons – molecule consisting only

of carbon and hydrogen– Nonpolar– Functional groups add chemical properties

4


Hydroxyl

Carbonyl

Carboxyl

Amino

Sulfhydryl

Phosphate

Methyl

Example

OH

O

C

O

OH

C

H

H

N

S H

O

proteins

proteinsH

H

Glycerol phosphate

Alanine

Cysteine

Alanine

Acetic acid

Acetaldehyde

Ethanol

COOH

NH2

HH

H

HH

C OHC

O

H C C

H

H

H

H CO

OHH

C

O H

NH

HCH3

H C HSCH2

NH2

OH OH H

P

O

P O–

O–

O

OCCCH

H H H

O H

HO C C

H C H

H

O–

O–

H

C

HO C C

H

FoundIn

carbo-hydrates,proteins,nucleicacids,lipids

carbo-hydrates,nucleicacids

proteins,lipids

proteins,nucleicacids

nucleicacids

FunctionalGroup

StructuralFormula

5

Isomers

• Molecules with the same molecular or empirical formula– Structural isomers– Stereoisomers – differ in how groups attached

• Enantiomers– mirror image molecules– chiral– D-sugars and L-amino acids

6


C

W

Y

W

Y

C

Z

X

Z

X

Mirror

7

Macromolecules

• Polymer – built by linking monomers• Monomer – small, similar chemical subunits

8


O

P

P

OH

HO

H

OH

H

OHOH

HH

H

O

Cellular Structure Polymer Monomer

Chromosome DNA strand Nucleotide

MonosaccharideStarchStarch grains in a chloroplast

5-carbon sugarPhosphate

group

Nitrogenous base

CH2OH

Car

bohy

drat

eN

ucle

ic A

cid

P

P

P

PP

P

P

G

C

T

A

A

T

P

A

P

P

P

P

G

C

P

P

T

A

G

C

P

9

AlaAla

ValVal

Ser ON

HC

H

OHH

CCH3

Intermediate filament Polypeptide Amino acid

Prot

ein


HO H H H H H H H H H HHHO C C C C C C C C C C C C

H H H H H H H H H H H

Adipose cell with fat dropletsTriglyceride

Fatty acid

Lipi

d

10

• Dehydration synthesis– Formation of large molecules by the removal of water– Monomers are joined to form polymers

• Hydrolysis– Breakdown of large molecules by the addition of

water– Polymers are broken down to monomers

HO

HO H

HO HH HHO

HO H HHO

a. Dehydration reaction b. Hydrolysis reaction

H2O H2O


11

Carbohydrates

• Molecules with a 1:2:1 ratio of carbon, hydrogen, oxygen

• Empirical formula (CH2O)n

• C—H covalent bonds hold much energy– Carbohydrates are good energy storage

molecules– Examples: sugars, starch, glucose

12

Monosaccharides

• Simplest carbohydrate• 6 carbon sugars play important roles• Glucose C6H12O6

• Fructose is a structural isomer of glucose• Galactose is a stereoisomer of glucose• Enzymes that act on different sugars can

distinguish structural and stereoisomers of this basic six-carbon skeleton

13

H

CH2OH

H

OH

OH HH

H

C

CC

C

C

C

C

H

C H

HO

OHH

OHH C

OHH C

OHH C

H

OH

C HH

OH

H

OH

H

OH

H

OH

H

OH HH

H

C

CC

C

C O

OH

OH HH

H

C

CC

C

OC

OH

OH

O

H23

5

14

6

5

4

3

2

1

23

5

6

14

23

5

14

α-glucose or

β-glucose

OO

CH2OH


14

Fructose Glucose Galactose

H OH

O

C

C

C

C

C

C

H

H

HO H

H OH

H OH

H OH

H

OC

C

C

C

C

H

H

HO H

OH

H OH

H OH

OC

C

C

C

C

C

H

H

H

HO H

OH

H OH

H OH

CH OH HO H

Stereo-isomer

Structuralisomer


15

Disaccharides

• 2 monosaccharides linked together by dehydration synthesis

• Used for sugar transport or energy storage• Examples: sucrose, lactose, maltose

OH

SucroseFructoseα-glucose

HO

CH2OH

H

OH

H

OHH

H

H

O

H

OH H

HO

HO

H

OH

H

OH OHH

H

O

H OH

OH H

HO

+

a. b.Maltose

HO

H

OH

H

OH OHH

H

O H

OH

H

OHOH

HH

H

O

OHHO

H2O

CH2OH CH2OH CH2OH CH2OH CH2OH

CH2OH CH2OH


16

Polysaccharides

• Long chains of monosaccharides– Linked through dehydration synthesis

• Energy storage– Plants use starch– Animals use glycogen

• Structural support– Plants use cellulose– Arthropods and fungi use chitin

17

Glycogen

Amylose + Amylopectin

b.

a. c. 3.3 µm


α-glucose

HO

CH2OH

H

OH

H

OH HH

H

O

OH4 1

α-1 4 linkages

CH2OH

OH

H

OH H

H

OCH2OH

OH

H

OH H

H

OCH2OH

OH

H

OH H

H

O

O O

H

α-1 4 linkage

a-1

CH2OH

O

H

OH

H

OH HH

H

O

CH2

H

OH

H

OH HH

H

O

O

CH2OH

H

OH

H

OH HH

H

O

6 linkage

b: © Asa Th oresen/Photo Researchers, Inc.; c: © J. Carson/Custom Medical Stock Photo

7.5 µm

18

HO

CH2OH

H

OH

H

OH HH

H

OCH2OH

H H

OH

H

OH HH

H

O

O

CH2OH

H

OH

H

OH HH

H

OOHH

HOH HH

CH2OHO

β-1 4 linkages

OH O O

O4 1


b: © Science VU/Visuals Unlimited

β-glucose

500 µmb.

a.

Nucleic acids

• Polymer – nucleic acids• Monomers – nucleotides

– sugar + phosphate + nitrogenous base– sugar is deoxyribose in DNA or ribose in RNA– Nitrogenous bases include

• Purines: adenine and guanine• Pyrimidines: thymine, cytosine, uracil

– Nucleotides connected by phosphodiester bonds

19

20

5 ́

28

7 6

394

5

1

NH2

O

P

O-

–O O CH2

Phosphate group

Sugar

Nitrogenous base

OH

NN

N

O

4 ́ 1 ́

2 ́3 ́

H in DNA

OH in RNA


21

5′

3′

P

P

P

P

OH

Phosphate group

O

O

NH2CC

NN

N

C

HN

CCH

O

H

H

OC

NC

H

N

CNH2

H

CH

a.

b.O

O

O

C

NC

H

N

CH3C

CH

H

O

O

C

NC

H

N

CH

CH

CC

NN

N

C

HN

CCH

H

O

4′

5′

1′

3′ 2′

4′

5′

1′

3′ 2′

4′

5′

1′

3′ 2′

4′

5′

1′

3′ 2′

Phosphodiester bonds

5-carbon sugar

Nitrogenousbase

NH2

GuanineAdenine

Purin

esPy

rimid

ines


Cytosine(both DNA and RNA)

Thymine(DNA only)

Uracil(RNA only)

Deoxyribonucleic acid (DNA)

• Encodes information for amino acid sequence of proteins– Sequence of bases

• Double helix – 2 polynucleotide strands connected by hydrogen bonds– Base-pairing rules

• A with T (or U in RNA)• C with G

22

23


5′ end

P

P

P

P

P

C

G

A

A

OH

T

TPhosphodiesterbonds

3′ end

Sugar–phosphate“backbone”

Hydrogenbondsbetween

nitrogenous bases

24

Ribonucleic acid (RNA)

• RNA similar to DNA except– Contains ribose instead of deoxyribose– Contains uracil instead of thymine

• Single polynucleotide strand• RNA uses information in DNA to specify

sequence of amino acids in proteins

25


P

P

P

P

PPP

P

P

P

P

P

P

P

P

G

C

G

C

T

A

A

A

A

T

T

GBases

Hydrogen bondingOccurs between base-pairs

P

P

PP

P

P

P

G

G

C

A

A

U

U

Bases

Deoxyribose-phosphatebackbone

Ribose-phosphatebackbone

RNA

DNA

26

Other nucleotides

• ATP adenosine triphosphate– Primary energy currency of the cell

• NAD+ and FAD+

– Electron carriers for many cellular reactions

4′

56

2

394

8

7

1′

3′ 2′

5′

1

CH2

OOO

O–

OH OH

NH2

N

N

N

N

O

–O O O OP P P

Triphosphate group

5-carbon sugar

O

Nitrogenous base(adenine)

O– O–


27

Proteins

Protein functions include:1. Enzyme catalysis 2. Defense3. Transport4. Support5. Motion6. Regulation7. Storage

28

• Proteins are polymers– Composed of 1 or more long, unbranched

chains– Each chain is a polypeptide

• Amino acids are monomers• Amino acid structure

– Central carbon atom– Amino group– Carboxyl group– Single hydrogen– Variable R group

29

CH2

CH2

CH3

CH2

OH H O

S H

S

CH2

CH2

O

CH2

NH2+

C C O–H3N+

C C O–H3N+

C C O–H3N +

C C O–H3N+

C C O–H3N+

C C O–H3N+

C C O–H3N+

C C O–H3N+C C O–H3N+

C C O–H3N+

C C O–H3N+

C C O–H3N+

C C O–H3N+

C C O–H3N+

C C O–H3N+ C C O–H 3N + C C O–H3N+

C C O–H3N+CH C O– C C O–NH3+

CH3

OH

CH2

OH

OH

H

OH

OH

CH3CH3

CH

CH2

OH

CH3CH3

CH

CH2

OH

NH2O

C

CH2

OH

O–O

C

CH2

CH2

CH2 NH3+

OH

CH2

CH2

CH2

OH

O–O

C

CH2

CH2

OH

NH2O

C

H C CH3

CH2

CH3

OH

H C OH

CH3

OH

CH2

CHC N

HC NH+

H O

HCH2

NHC

H O

CH2

H O

OH

CH2

H O

CH2

CH2

NH

NH2

C

OH

CH2

NH3+

Nonpolar Polar uncharged Charged

Proline(Pro)

Methionine(Met)

Cysteine(Cys)

Tryptophan(Trp)

Tyrosine(Tyr)

Phenylalanine(Phe)

Glycine(Gly)

Leucine(Leu)

Glutamine(Gln)

Isoleucine(Ile)

Asparagine(Asn)

Asparticacid(Asp)

Histidine(His)

Lysine(Lys)

Glutamic acid(Glu)

Threonine(Thr) Arginine

(Arg)

(Ser)Serine

(Ala)Alanine

Non

arom

atic

Aro

mat

icSp

ecia

l fun

ctio

n


Valine(Val)

30

• Amino acids joined by dehydration synthesis– Peptide bond

RH

H

R

H O

R

OH

RH

OH

H2O

H

O

H

OH OH

OHH

CC C C

CC CC

N

N N

NH H

Amino acid

Dipeptide

Amino acid

31

4 Levels of structure

• The shape of a protein determines its function

1. Primary structure – sequence of amino acids2. Secondary structure – interaction of groups

in the peptide backbone helix sheet

4 Levels of structure

3. Tertiary structure – final folded shape of a globular protein

– Stabilized by a number of forces– Final level of structure for proteins consisting

of only a single polypeptide chain

4. Quaternary structure – arrangement of individual chains (subunits) in a protein with 2 or more polypeptide chains

32

33

••••••

••••••

•••

••

•••

•••••••••••••••

•••••••

••••••

••••••

••

•••

•••••••••••••••

••••

Primary Structure

Secondary Structure Secondary Structure

Tertiary Structure Quaternary Structure

N

H

H H

C C C N C C NC

O

O H

OH H

R

R

R

β-pleated sheet α-helix

C

H

R


The primary structure can foldInto a pleated sheet, or turn into a helix

Additional structural characteristics

• Motifs – Common elements of secondary structure

seen in many polypeptides– Useful in determining the function of unknown

proteins• Domains

– Functional units within a larger structure– Most proteins made of multiple domains that

perform different parts of the protein’s function34

35

Domain 3 Domain 2

Domain 1

DomainsMotifs


β-α-βmotif

Helix-turn-Helixmotif

36

• Once thought newly made proteins folded spontaneously

• Chaperone proteins help protein fold correctly

• Deficiencies in chaperone proteins implicated in certain diseases– Cystic fibrosis is a hereditary disorder

• In some individuals, protein appears to have correct amino acid sequence but fails to fold

Chaperones

37

Chance for protein to refold

ADP + P

Cap

ATP


Correctlyfoldedprotein

Misfoldedprotein

Chaperoneprotein

Denaturation

• Protein loses structure and function

• Due to environmental conditions– pH– Temperature– Ionic concentration of

solution

38

Properly folded protein

Denaturation

Denaturedprotein


39

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40

Lipids

• Loosely defined group of molecules with one main chemical characteristic– They are insoluble in water

• High proportion of nonpolar C—H bonds causes the molecule to be hydrophobic

• Fats, oils, waxes, and even some vitamins

41

Fats• Triglycerides

– Composed of 1 glycerol and 3 fatty acids• Fatty acids

– Need not be identical– Chain length varies– Saturated – no double bonds between carbon

atoms• Higher melting point, animal origin

– Unsaturated – 1 or more double bonds• Low melting point, plant origin

– Trans fats produced industrially

42

C

C

H

HCH

HCH

HOC

HCH CH

HCH

HCH

HCH

HCH

HCH

HCH

CH H

CHC C

HH H HC

HC C

HO

H

HH HCH

HCH

HOC

HCH CH

HCH

HCH

HCH

HCH

HCH

HCH

CH

CHCH

CHH H

CHCH

CH H

OH

H HCH

HCH

HOC

HCH CH

HCH

HCH

HCH

HCH

HCH

HCH

CH H

CH HCH

CH

HC

H HCHH

CH H

CO

OC

HCH

HCH

HCH

HCH CH

HCH

HCH

HCH

HCH

HCH

HCH

HCH

HCH

HCH

HCH

HCH

O

OC

HCH

HCH

HCH

HCH CH

HCH

HCH

HCH

HCH

HCH

HCH

HCH

HCH

HCH

HCH

HCH

O

OC

HCH

HCH

HCH

HCH CH

HCH

HCH

HCH

HCH

HCH

HCH

HCH

HCH

HCH

HCH

HCH

HCH

HCH

H

HCH

HCH

H

HCH

HCH

HO

H

H

Structural Formula Structural Formula

Space-Filling Model Space-Filling Model

a. b.


43

Phospholipids

• Composed of– Glycerol– 2 fatty acids – nonpolar “tails”– A phosphate group – polar “head”

• Form all biological membranes

44

Non

pola

r Hyd

roph

obic

Tai

lsPo

lar H

ydro

phili

c H

eads

Choline

Phosphate

Glycerol

a. b. c. d.

CH2

CH2

CH2H2C

O

OO P

CO O

OO

CH

C

O-

N+(CH3)3


Fattyacid

Fattyacid

CHCH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH3

CHCH2CH2CH2CH2CH2CH2CHCHCH2CH2CH2CH2CH2CH2CH2CH3

45

• Micelles – lipid molecules orient with polar (hydrophilic) head toward water and nonpolar (hydrophobic) tails away from water

a.

WaterLipid head(hydrophilic)

Lipid tail(hydrophobic)


• Phospholipid bilayer – more complicated structure where 2 layers form– Hydrophilic heads point outward– Hydrophobic tails point inward toward each

other

46

b.

Water

Water


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