Clapiei

Tle Clemisiiy of Oiganic

Molecules

1
2
!"# %&'()*+ ,-./+0./1
%&'()*+ 2-./+0./1
! caibon
! lydiogen aioms.

( Classes
(3*-2-./+0./1) exisi in living oiganisms4
! 5(&3-678&(9/1
! :*;*81
! <&-9/*)1
! =0+./*+ >+*81
3
?)-&'()*+ @/&101 %&'()*+ ,-./+0./1
Caibon Clemisiiy
! Caibon is a veisaiile aiom.
Ii las foui eleciions in an ouiei slell ilai lolds eigli
eleciions.
Caibon can slaie iis eleciions wiil oilei aioms io foim
up io A%BC covaleni bonds.
C
?
?
?
?
Figure 3.1a
Carbon skeletons vary in length
Figure 3.1b
Double bond
Carbon skeletons may have double bonds,
which can vary in location
Figure 3.1c
Carbon skeletons may be:
unbranched branched
Figure 3.1d
Carbon skeletons may be arranged in rings
! Tle simplesi oiganic compounds aie
678&-+(&3-)1D wlicl coniain only caibon and
lydiogen aioms.
! Tle simplesi lydiocaibon is meilane, a single
caibon aiom bonded io foui lydiogen aioms.
10
E6/ 5(&3-) FG/./9-) ()8 A0)+9*-)(.
H&-0;1

Tle caibon clain of an oiganic molecule is called
iis sleleion oi baclbone.
A0)+9*-)(. '&-0;1 aie clusieis of specifc aioms
bonded io ile caibon sleleion wiil claiacieiisiic
siiuciuies and funciions.
! Deieimine ile clemical ieaciiviiy and polaiiiy
of oiganic molecules
Table .:
12
?1-2/&1
?1-2/&1 aie oiganic molecules ilai lave
ideniical moleculai foimulas bui a dieieni
aiiangemeni of aioms.
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glyceraldehyde dihydroxyacetone
OH OH
H H
H C C C H
O
OH OH
H O
H C C C H
H
13
I*-2-./+0./1
Caibolydiaies, lipids, pioieins, and nucleic
acids aie called 3*-2-./+0./1.
! Usually consisi of many iepeaiing uniis
Eacl iepeaiing unii is called a 2-)-2/&.
A molecule composed of monomeis is
called a ;-.72/& (many paiis).
- Example: amino acids (monomei) aie
joined iogeilei io foim a pioiein
(polymei)
Copyright The McGraw-Hill Companies, Inc. Permission required for reproduction or display.
Fig. .
Biomolecules
Polymer Category Subunit(s)
Polysaccharide Carbohydrates* Monosaccharide
Lipids
Proteins*
Nucleic acids*
Glycerol and fatty acids Fat
Polypeptide Amino acids
Nucleotide DNA,RNA
*Polymers
The McGraw Hill Companies, Inc./John Thoeming, photographer
15
F7)96/1*1 ()8 J/'&(8(9*-)
A 8/678&(9*-) &/(+9*-) is a clemical ieaciion
in wlicl subuniis aie joined iogeilei by ile
foimaiion of a covaleni bond and waiei is :%FE
duiing ile ieaciion.
! Used io conneci monomeis iogeilei io male polymeis
! Example: foimaiion of siaicl (polymei) fiom glucose
subuniis (monomei)

A 678&-.71*1 ieaciion is a clemical ieaciion in
wlicl a waiei molecule is >JJKJ io bieal a
covaleni bond.
! Used io biealdown polymeis inio monomeis
! Example: digesiion of siaicl inio glucose monomeis
monomer
OH
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Synthesis and Degradation of Biomolecules
monomer OH +
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+
monomer
H
monomer OH
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Synthesis and Degradation of Biomolecules
monomer monomer
H
2
O
OH H +
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monomer monomer
monomer monomer
Dehydration
reaction
H
2
O
OH H
a. Synthesis of a biomolecule
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+
monomer monomer
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H
2
O
monomer monomer
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monomer monomer
Dehydration
reaction
H
2
O
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monomer monomer
Hydrolysis
reaction
OH H
b. Degradation of a biomolecule
H
2
O
monomer monomer
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monomer monomer
monomer monomer
dehydration
reaction
monomer monomer
H
2
O
OH H
OH H
b. Degradation of a biomolecule
a. Synthesis of a biomolecule
H
2
O
monomer monomer
hydration
reaction
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26
F7)96/1*1 ()8 J/'&(8(9*-)
Enzymes aie iequiied foi cells io caiiy oui
delydiaiion synilesis and lydiolysis ieaciions.
! An /)L72/ is a molecule ilai speeds up a
clemical ieaciion.
Enzymes aie noi consumed in ile ieaciion.
Enzymes aie noi clanged by ile ieaciion.
5>CI%MNJC>EKF O :?<?JF
Piopeiiies of:
27
!"P 5(&3-678&(9/1
Funciions:
! Eneigy souice
! Piovide building maieiial (siiuciuial iole)

Coniain caibon, lydiogen and oxygen in a i:::i iaiio
Vaiieiies: monosacclaiides, disacclaiides, and
polysacclaiides
29
A 2-)-1(++6(&*8/ is a single sugai molecule.
Also called simple sugais
Have a baclbone of io y caibon aioms
Examples:
! Glucose (blood), fiuciose (fiuii) and galaciose
M/Q-1/1 - six caibon aioms
! Ribose and deoxyiibose (in nucleoiides)
</)9-1/1 - fve caibon aioms
Monosaccharides
Copyright The McGraw-Hill Companies, Inc. Permission required for reproduction or display.
Fig. .6
H
C
HO
a.
H OH
OH
6
5
4
3
1
c. d.
O O
H
O
H
H
H
OH
OH
OH H
HO
b.
C
6
H
12
O
6
CH
2
OH CH
2
OH
C
C
H
O
C
2
C
OH
H
H
Steve Bloom/Taxi/Getty
Glucose
31
J*1(++6(&*8/1
A 8*1(++6(&*8/ coniains iwo
monosacclaiides joined iogeilei by
delydiaiion synilesis.
Examples:
! Laciose (mill sugai) is composed of galaciose
and glucose.
! Suciose (iable sugai) is composed of glucose and
fiuciose.
! Maliose is composed of iwo glucose molecules.
O O
OH
glucose C
6
H
12
O
6
HO
H H
+
CH
2
OH
CH
2
OH
glucose C
6
H
12
O
6
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Synthesis and Degradation of Maltose
glucose C
6
H
12
O
6
CH
2
OH
O O
OH HO
H H
+
dehydration reaction
glucose C
6
H
12
O
6
CH
2
OH
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O O O O
OH
water
HO
H H
O + +
dehydration reaction
H
2
O
maltose C
12
H
22
O
11
glucose C
6
H
12
O
6
CH
2
OH CH
2
OH CH
2
OH CH
2
OH
glucose C
6
H
12
O
6
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O O
O O
OH
water
monosaccharide disaccharide water
HO
H H
O
monosaccharide
+
+ +
+
de h yd r ation reaction
H
2
O
maltose C
12
H
22
O
11
glucose C
6
H
12
O
6
CH
2
OH CH
2
OH CH
2
OH CH
2
OH
glucose C
6
H
12
O
6
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O O
O
maltose C
12
H
22
O
11

CH
2
OH CH
2
OH
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O O
water
O
+
H
2
O
maltose C
12
H
22
O
11
CH
2
OH CH
2
OH
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maltose C
12
H
22
O
11
CH
2
OH
O O
water
O
+
hydrolysis reaction
H
2
O
CH
2
OH
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O O O O
OH
water
HO
H H
O
+ +
hydrolysis reaction
H
2
O
maltose C
12
H
22
O
11
glucose C
6
H
12
O
6
CH
2
OH CH
2
OH CH
2
OH CH
2
OH
glucose C
6
H
12
O
6
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O O O O
OH
water
monosaccharide disaccharide water
HO
H H
O
glucose C
6
H
12
O
6

monosaccharide
+
+ +
+
hydrolysis reaction
H
2
O
maltose C
12
H
22
O
11

CH
2
OH
glucose C
6
H
12
O
6

CH
2
OH CH
2
OH CH
2
OH
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glucose C
6
H
12
O
6
water
monosaccharide disaccharide water monosaccharide
+ +
dehydration reaction
hydrolysis reaction
maltose C
12
H
22
O
11
glucose C
6
H
12
O
6
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<-.71(++6(&*8/1
A polysaccharide is a polymer of monosaccharides.
Examples:
! Starch provides energy storage in plants.
! Glycogen provides energy storage in animals.
! Cellulose is found in the cell walls of plants.
! Chitin is found in the cell walls of fungi and
exoskeleton of some animals.
! Peptidoglycan is found in the cell walls of bacteria.
a. Starch
b . Glycogen
Amylose:
nonbranched
starch
granule
glycogen
granule
Amylopectin:
branched
150 nm
250 m
Copyiigli Tle McGiaw-Hill Companies, Inc. Peimission iequiied foi iepioduciion oi display.
a: }eiemy Buigess]SPL]Ploio Reseaicleis, Inc.; b: Don W. Fawceii]Ploio Reseaicleis, Inc.
!"! :*;*81
Lipids are varied in structure.
Large nonpolar molecules that are insoluble in water
Functions:
! Long-term energy storage
! Structural components
! Cell communication and regulation
! Protection

Varieties: fats, oils, phospholipids, steroids, waxes

E&*'.7+/&*8/14 :-)'RE/&2
K)/&'7 F9-&('/
! Also called S(91 and -*.1
! Funciions: long-ieim eneigy sioiage and
insulaiion
! Consisi of ONE glyceiol molecule linled io
THREE faiiy acids by delydiaiion synilesis
Copyright The McGraw-Hill Companies, Inc. Permission required for reproduction or display.
C H
H
C H
C H
H
OH
OH
OH
glycerol
a. Formation of a fat
Copyright The McGraw-Hill Companies, Inc. Permission required for reproduction or display.
+
C H
H
C H
C H
H
C
O
C
O
H
H
H H H H H
H C C C C C
H H H H H
H H H H H H H
C C C C C C C
H H H H H H
OH
OH
OH
C
O
H
H
H H H
H
C
C
C C C
H
H H
in
HO
HO
HO
3 fatty acids glycerol
a. Formation of a fat
Copyright The McGraw-Hill Companies, Inc. Permission required for reproduction or display.
3 H
2
O
3 H
2
O
+
C H
H
C H
C H
H
C
O
C
O
H
H
H H H H H
H C C C C C
H H H H H
H H H H H H H
C C C C C C C
H H H H H H
OH
OH
OH
C
O
H
H
H H H
H
C
C
C C C
H
H H
in
HO
HO
HO
3 water
molecules
3 fatty acids glycerol
a. Formation of a fat
Copyright The McGraw-Hill Companies, Inc. Permission required for reproduction or display.
in
3 H
2
O
3 H
2
O
+
C H
H
C H
C H
H
C
O
C
O
C
O
H
H
H H
C C C C C
H H H H H
H
H
H
H H H
H H H H H H H
C C
H H
H
H H
H H H H H
C C C C C
C
C
C C C
H
H H
H
H
H H H H H
H C C C C C
H H H H H
H H H H H H H
C C C C C C C
H H H H H H
H
H
H H H
H
C
C
C C C
H
H H
in
OH
OH
OH HO
HO
HO
H
H
H
H
C
C
C O
H
O C
O
O
C
H
O
C
fat molecule
3 water
molecules
3 fatty acids glycerol
a. Formation of a fat
51
Faiiy acids aie eiilei 0)1(90&(9/8 oi 1(90&(9/8.
! B)1(90&(9/8 - one oi moie double bonds beiween
caibons
Tend io be liquid ai ioom iempeiaiuie
- Example: plani oils

! F(90&(9/8 - no double bonds beiween caibons
Tend io be solid ai ioom iempeiaiuie
- Examples: buiiei, laid
Triglycerides: Long-Term Energy Storage
Copyright The McGraw-Hill Companies, Inc. Permission required for reproduction or display.
Fig. .io
in
3 H
2
O
3 H
2
O
+
C H
H
C H
C H
H
C
O
C
O
C
H
H H H
C
H
C
H
C
H
H
C
O
C
H
H
C
H
H
C
H
H
C
H
C
H
C
H
H
C
H
C
H
C
H
H
C
H
C
H
C
H
H
C
H
H
H
C
H
H
H C
H
H H H
C
H
C
H
C
H
H
C
O
C
H
H
C
H
H
C
H
H
C
H
H H H
C
H
C
H
C
H
H
C
H
H
C
H
H
C
H
H
C
O
H
H
H H
C C C C C
H H H H H
H
H
H
H H H
H H H H H H H
C C
H H
H
H H
H H H H H
C C C C C
C
C
C C C
H
H H
H
H
H H H H H
H C C C C C
H H H H H
H H H H H H H
C C C C C C C
H H H H H H
H
H
H H H
H
C
C
C C C
H
H H
in
OH
OH
OH HO
HO
HO
HO
HO
unsaturated fat
unsaturated fatty acid with double bonds (yellow)
corn corn oil
butter
H
H
H
H
C
C
C O
H
O C
O
O
C
H
O
C
fat molecule
3 water
molecules
3 fatty acids glycerol
a. Formation of a fat
Types of fatty acids b. Types of fats c.
saturated fat saturated fatty acid with no double bonds
mil
Most animal fats
have a high proportion of saturated fatty acids,
can easily stack, tending to be solid at room
temperature, and
contribute to atherosclerosis, in which lipid-containing
plaques build up along the inside walls of blood
vessels.
! Mosi plani and fsl oils iend io be
ligl in unsaiuiaied faiiy acids
liquid ai ioom iempeiaiuie
Good souice of dieiaiy fais
55
<6-1;6-.*;*814 ,/23&()/ 5-2;-)/)91
Siiuciuie is similai io iiiglyceiides
! Consisi of ONE glyceiol molecule linled io TWO faiiy
acids and a modifed plosplaie gioup
Tle S(997 (+*81 aie )-);-.(& and 678&-;6-3*+.
Tle modifed ;6-1;6(9/ '&-0; is ;-.(& and
678&-;6*.*+.
Funciion: foim plasma membianes
In waiei, plosplolipids aggiegaie io foim a lipid
bilayei.
! Polai plosplaie leads aie oiienied iowaids ile waiei.
! Nonpolai faiiy acid iails aie oiienied away fiom waiei.
Nonpolai faiiy acid iails foim a lydioplobic coie.
Copyright The McGraw-Hill Companies, Inc. Permission required for reproduction or display.
Fig. .ii
.
O
R O P O
3
O
Polar
Head
glycerol
fatty acids
phosphate
Phospholipid structure a.
Nonpolar Tails
b. Plasma membrane of a cell
CH
2

CH
2

CH
2

O O
C
CH
2

CH
2

CH
2

CH
2

CH
2

CH
2

CH
2

CH
2

CH
2

CH
2

CH
2

CH
2

CH
2

CH
2

CH
2

CH
2

CH
3

CH
2

O
C
CH
2

CH
2

CH
2

CH
2

CH
2

CH
2

i
n
s
i
d
e

c
e
l
l


o
u
t
s
i
d
e


c
e
l
l


CH
1
2
Phospholipids Form
Membranes
57
Composed of foui fused caibon iings
! Vaiious funciional gioups aiiacled io ile caibon sleleion
Funciions: componeni of animal cell membiane,
iegulaiion
Clolesieiol males ile bilayei siiongei, moie exible bui less
uid, and less peimeable io waiei-soluble subsiances sucl as
ions and monosacclaiides.
Examples: clolesieiol, iesiosieione, esiiogen
Clolesieiol is ile piecuisoi molecule foi seveial oilei
sieioids.
Steroids: Four Fused Carbon Rings
Copyright The McGraw-Hill Companies, Inc. Permission required for reproduction or display.
b . T e s t o s t e r o n e
HO
a. Cholesterol
c. Estrogen
OH
CH
3
O
CH
3
OH
CH
3
CH
3
HC CH
3
HC CH
3
HO
(CH
2
)
3
Ernest A. Janes/Bruce Coleman/Photoshot
CH
3
CH
3
Steroid Diversity
59
Long-clain faiiy acid bonded io a long-clain
alcolol
Solid ai ioom iempeiaiuie
Waieipioof
Resisiani io degiadaiion
Funciion: pioieciion
Examples: eaiwax, plani cuiicle, beeswax
Waxes
60
T(Q/1
(" 3"
Copyiigli Tle McGiaw-Hill Companies, Inc. Peimission iequiied foi iepioduciion oi display.
a: Das Foioaicliv]Peiei Ainold, Inc.; b: Maiila Coopei]Peiei Ainold, Inc.
<C%EK?=F O =B5:K?5 >5?JF
Piopeiiies of:
61
62
!"U <&-9/*)1
Pioieins aie polymeis of (2*)- (+*81 linled
iogeilei by ;/;9*8/ 3-)81.
! A pepiide bond is a covaleni bond beiween amino
acids.
Two oi moie amino acids joined iogeilei aie
called ;/;9*8/1.
! Long clains of amino acids joined iogeilei aie
called ;-.7;/;9*8/1.
A ;&-9/*) is a polypepiide ilai las folded inio
a paiiiculai slape and las funciion.

63
A0)+9*-)1 -S <&-9/*)1

,/9(3-.*12
! Mosi enzymes aie pioieins ilai aci as caialysis io acceleiaie clemical
ieaciions wiilin cells.
F0;;-&9
! Keiaiin and collagen
E&()1;-&9
! Hemoglobin and membiane pioieins
J/S/)1/
! Aniibodies
C/'0.(9*-)
! Hoimones aie iegulaioiy pioieins ilai inuence ile meiabolism of
cells.
,-9*-)
! Muscle pioieins and micioiubules
Copyright The McGraw-Hill Companies, Inc. Permission required for reproduction or display.
C
H
R
acidic
group
amino
group
COOH
H
2
N
R = rest of molecule
Amino Acids: Protein Monomers
There are 20 different common amino acids.
Amino acids differ by their R groups.

Copyright The McGraw-Hill Companies, Inc. Permission required for reproduction or display.
H
Sample Amino Acids with Nonpolar (Hydrophobic) R Groups
C C
H
O
O
C
H
C
O
O
C
H
C
O
O
C C
H
O
O
S
C C
O
O
C C
H
O
O
C
O
C C
H
O
O
C C
H
O
O
C
O
C C
H
O
O
C
O O
C C
H
O
O
C
C C
H
O
O
C
H
C
O
O
C
H
C
O
O
C
H
C
O
O
C
C
H
O
O
C C
O
O
CH
2
H
3
N
+
H
3
C
CH
3
H
3
N
+
(CH
2
)
2
CH
3
H
3
N
+
CH
2
H
3
N
+
H
3
N
+
CH
2
SH
OH
CH
H
3
N
+
H
3
N
+
H
3
N
+
CH
2
(CH
2
)
2
H
3
N
+
CH
2
N
+
H
3
OH
H
3
N
+
CH
3
NH
2
H
3
N
+
H
3
N
+
CH
2
CH
2
COO
-
H
3
N
+ CH
2
CH
2
CH
2
H
3
N
+
(CH
2
)
3
NH
N
+
H
2
NH
2
H
3
N
+
CH
2
NH
N
+
H
histidine (His) arginine (Arg) aspartic acid (Asp) lysine (Lys) glutamicacid (Glu)
asparagine (Asn) threonine (Thr)
Sample Amino Acids with Polar (Hydrophilic) R Groups
proline (Pro) leucine (Leu) phenylalanine (Phe) methionine (Met) valine (Val)
CH
CH
3
CH
2
CH
CH
2
H
2
N
+
H
2
C

glutamine (Gln)
cysteine (Cys) serine (Ser)
tyrosine (Tyr)
OH
CH
Sample Amino Acids with Ionized R Groups
CH
3
NH
2
H
CH
2
amino acid
amino group
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Synthesis and Degradation of a Peptide
+
amino acid
amino acid
acidic group amino group
Copyiigli Tle McGiaw-Hill Companies, Inc. Peimission iequiied foi iepioduciion oi display.
dehydration reaction
Copyiigli Tle McGiaw-Hill Companies, Inc. Peimission iequiied foi iepioduciion oi display.
amino acid
amino acid
acidic group amino group
water
peptide bond
dipeptide
dehydration reaction
amino acid
amino acid
acidic group amino group
Copyiigli Tle McGiaw-Hill Companies, Inc. Peimission iequiied foi iepioduciion oi display.
water
peptide bond
dipeptide
dehydration reaction
hydrolysis reaction
water
peptide bond
dipeptide
amino acid
amino acid
acidic group amino group
Copyiigli Tle McGiaw-Hill Companies, Inc. Peimission iequiied foi iepioduciion oi display.
71
:/@/.1 -S <&-9/*) F9&0+90&/

Pioieins cannoi funciion piopeily unless iley
fold inio ileii piopei slape.
! Wlen a pioiein loses ii piopei slape, ii said io be
8/)(90&/8.
Exposuie of pioieins io ceiiain clemicals, a clange
in pH, oi ligl iempeiaiuie can disiupi pioiein
siiuciuie.

Pioieins can lave up io foui levels of siiuciuie:
! <&*2(&7
! F/+-)8(&7
! E/&9*(&7
! V0(9/&)(&7
Several Roles for proteins:
Enzymes**
Structural
Storage
Contractile
Transport
Defensive
Signal
Receptor
73
A-0& :/@/.1 -S <&-9/*) F9&0+90&/

! <&*2(&7
Tle sequence of amino acids
! F/+-)8(&7
Claiacieiized by ile piesence of alpla lelices and
beia (pleaied) sleeis leld in place wiil lydiogen
bonds
! E/&9*(&7
Final oveiall iliee-dimensional slape of a
polypepiide
Siabilized by ile piesence of lydioplobic
inieiaciions, lydiogen bonding, ionic bonding, and
covaleni bonding
! V0(9/&)(&7
Consisis of moie ilan one polypepiide
Copyright The McGraw-Hill Companies, Inc. Permission required for reproduction or display.
COO

hydrogen bond
Primary Structure
This level of structure
is determined by the
sequence of amino
acids coded by a
gene that joins to
form a polypeptide.
Secondary Structure
Hydrogen bonding
between amino acids
causes the polypeptide
to form an alpha helix
or a pleated sheet.
! (beta) sheet = pleated sheet
" alpha) helix
C
N
R
C
R
C
N
C
R
C
N
C
R
N
C
R
N
R
N
C
N
R
CH
CH
CH
CH
CH
CH
CH
CH
Tertiary Structure
disulfide bond
Quaternary Structure
This level of structure
occurs when two or more
folded polypeptides interact
to perform a biological function.
hydrogen bond
Interactions of amino
acid side chains with
water, covalent bonding
between R groups, and
other chemical interactions
determine the folded
three-dimensional shape
of a protein.
peptide bond
amino acid
H
3
N+
C
C
C
C
C
C
C
C
C
C
C
C
C
C
C
C
C
C
C
C
C
C
R
R
R
R
R
R
R
R
R
O
O
O
O
O
O
O
O
O
O
O
O
N
N
N
N
N
N
N
N
N
N
N
C
H
H
H
H
H H
H
H
H
H
C
O
O
O
O
O
O
O
H
H
H
H
H
H
! Pioieins consisiing of one polypepiide lave iliee
levels of siiuciuie.
! Pioieins consisiing of moie ilan one polypepiide
clain lave a fouiil level, quaieinaiy siiuciuie.
Primary
Single chain
Secondary
Pleated sheet
Alpha Helix
Tertiary
Quaternary
77
KQ(2;./1 -S A*3&-01 <&-9/*)1
(" 3" +"
Copyiigli Tle McGiaw-Hill Companies, Inc. Peimission iequiied foi iepioduciion oi display.
a: Gregory Pace/Corbis; b: Ronald Siemoneit/Corbis Sygma; c: Kjell Sandved/Visuals Unlimited
! A pioieins iliee-dimensional slape
iypically iecognizes and binds io anoilei molecule and
enables ile pioiein io caiiy oui iis specifc funciion in a
cell.
79
<&-9/*)RA-.8*)' J*1/(1/1
56(;/&-)/ ;&-9/*)1 lelp pioieins fold inio ileii
noimal slape.
! Defecis in clapeione pioieins may play a iole in seveial
luman diseases sucl as Alzleimei disease and cysiic
fbiosis.
<&*-)1 aie misfolded pioieins ilai lave been
implicaied in a gioup of faial biain diseases
lnown as TSEs.
! Mad cow disease is one example of a TSE disease.
80
!"W =0+./*+ >+*81
Nucleic acids aie polymeis of )0+./-9*8/1.

Two vaiieiies of nucleic acids:
! J=> X8/-Q7&*3-)0+./*+ (+*8Y
Geneiic maieiial ilai sioies infoimaiion foi iis own
ieplicaiion and foi ile sequence of amino acids in
pioieins.
! C=> X&*3-)0+./*+ (+*8Y
Peifoim a wide iange of funciions wiilin cells
wlicl include pioiein synilesis and iegulaiion of
gene expiession
81
F9&0+90&/ -S ( =0+./-9*8/
Eacl nucleoiide is composed of iliee paiis:
! > ;6-1;6(9/ '&-0;
! > ;/)9-1/ 10'(&
! > )*9&-'/)R+-)9(*)*)' X)*9&-'/)-01Y 3(1/
Tleie aie fve iypes of nucleoiides found in nucleic acids.
! J=> coniains (8/)*)/, '0()*)/, +79-1*)/, and 9672*)/.
! C=> coniains (8/)*)/, '0()*)/, +79-1*)/, and 0&(+*..
Nucleoiides aie joined iogeilei by a seiies of delydiaiion
synilesis ieaciions io foim a lineai molecule called a
siiand.
Copyright The McGraw-Hill Companies, Inc. Permission required for reproduction or display.
S
C
O
P
nitrogen-
containing
base
pentose sugar
5'
4'
1'
2'
3'
phosphate
Nucleotides
Copyright The McGraw-Hill Companies, Inc. Permission required for reproduction or display.
S
C
O

O P
O
O
O

P
nitrogen-
containing
base
phosphate
pentose sugar
Nucleotide structure a.
5'
4' 1'
2'
3'
Copyright The McGraw-Hill Companies, Inc. Permission required for reproduction or display.
S
C
O

O
P
O
O
O

H
O
C C
C C
H
H
H
H
P
nitrogen-
containing
base
phosphate
pentose sugar deoxyribose (in DNA)
Nucleotide structure a.
OH
OH
CH
2
OH
5'
4' 1'
2'
3'
b. Deoxyribose versus ribose
Copyright The McGraw-Hill Companies, Inc. Permission required for reproduction or display.
S
C
O
O
P O
O
O

H
O
C
C
C C
H
H
H
H
O
C C
C C
H
H
H
H
P
nitrogen-
containing
base
phosphate
pentose sugar ribose (in RNA) deoxyribose (in DNA)
Nucleotide structure a.
OH OH OH
OH
OH
CH
2
OH CH
2
OH
5'
4' 1'
2'
3'
b. Deoxyribose versus ribose
Copyright The McGraw-Hill Companies, Inc. Permission required for reproduction or display.
H
O
N
N
H
O
N
C
C
C
C
C
C
C C
H
O
N
H
N
N
N
N
H
N
N
N
C
C
C
C T U
G A
Purines Pyrimidines
HN CH
CH
CH
CH
CH
HC
CH
HN
CH
guanine adenine uracil in RNA
Pyrimidines versus purines c.
cytosine thymine in DNA
NH
2
HN
CH
3
NH
2
H
2
N
O O
O
Copyright The McGraw-Hill Companies, Inc. Permission required for reproduction or display.
S
C
O
O
P O
O
O

H
O
C
C
C C
H
H
H
H
O
C C
C C
H
H
H
H
O
N
N
H
O
N
C
C
C
C
C
C
C C
H
O
N
H
N
N
N
N
H
N
N
N
C
C
C
H
C T U
G A
P
nitrogen-
containing
base
phosphate
pentose sugar ribose (in RNA) deoxyribose (in DNA)
Nucleotide structure a.
Purines Pyrimidines
OH OH OH
OH
OH
HN CH
CH
CH
CH
CH
HC
CH
HN
CH
guanine adenine uracil in RNA
Pyrimidines versus purines c.
cytosine thymine in DNA
CH
2
OH CH
2
OH
NH
2
HN
CH
3
NH
2
H
2
N
O O
O
5'
4' 1'
2'
3'
b. Deoxyribose versus ribose
88
F9&0+90&/ -S J=> ()8 C=>
! Tle baclbone of ile nucleic acid siiand is composed
of alieinaiing sugai-plosplaie molecules.
! RNA is piedominaiely a single-siianded molecule.
! DNA is a double-siianded molecule.
DNA is composed of iwo siiands leld iogeilei by
lydiogen bonds beiween ile niiiogen-coniaining
bases. Tle iwo siiands iwisi aiound eacl oilei io
foim a double lelix.
- Adenine lydiogen bonds wiil ilymine
- Cyiosine lydiogen bonds wiil guanine
Tle bonding beiween ile nucleoiides in DNA is
iefeiied io as +-2;./2/)9(&7 3(1/ ;(*&*)'.
Claiga's Rule
89
Copyright The McGraw-Hill Companies, Inc. Permission required for reproduction or display.
Fig. .iq
O
H
S
S
S
S
P
P
P
P
N
N
N
N
N
N
N
N
N
N
N
N
CH
3
NH
2
NH
2
Backbone
NH
2
Cytosine
Phosphate
Ribose
Adenine
Uracil
Guanine
C
G
P
S
A
U
U
G
A
C
O
Nitrogen-containing
bases
O O
RNA Structure
Copyright The McGraw-Hill Companies, Inc. Permission required for reproduction or display.
A
T
N
N
N H
O
N H
H
N
N
N
H
H
O
N H O
N
N
N
N
C
N
s u g a r
s u g a r
O
N H
N
A
A
T
G
G
C
G
C
C
c. Complementary base pairing
Sugar
Thymine
Adenine
Phosphate
Guanine
Cytosine
cytosine (C) guanine (G)
sugar
sugar
thymine (T) adenine (A)
CH
3
Double helix b. a. Space-filling model
C
G
P
S
A
T
#
#
#
#
H
T
Photodisk Red/Getty RF
DNA Structure
Complementary
Base Pairing in
DNA
93
> F;/+*(. =0+./-9*8/4 >E<
ATP (adenosine iiiplosplaie) is composed of adenine,
iibose, and iliee plosplaies.
ATP is a ligl-eneigy molecule due io ile piesence of ile
lasi iwo unsiable plosplaie bonds.
Hydiolysis of ile ieiminal plosplaie bond yields:
! Tle molecule ADP (adenosine diplosplaie)
! An inoiganic plosplaie
! Eneigy io do cellulai woil
ATP is called ile eneigy cuiiency of ile cell.
Copyright The McGraw-Hill Companies, Inc. Permission required for reproduction or display.
ATP
N
N
N
N
+ + P P P P P P N
N
N
N
ENERGY
phosphate diphosphate
ADP
triphosphate
ATP b.
NH
2
NH
2
H
2
O
adenosine triphosphate c. a.
adenosine adenosine
c: Jennifer Loomis / Animals Animals / Earth Scenes