Carbon Compounds in Cells

Chapter 3
 Importance of Carbon

Carbon permeates the world of life—from

the energy-requiring activities and
structural organization of cells, to physical
and chemical conditions that span the
globe and influence ecosystems
everywhere.
 Humans and Global Warming
• Fossil fuels are rich in carbon

• Use of fossil fuels releases CO2 into

atmosphere

• Increased CO2 may contribute to global

warming
Organic Compounds
Hydrogen and other elements
covalently bonded to carbon

Carbohydrates
Lipids
Proteins
Nucleic Acids
 Carbon’s Bonding Behavior
• Outer shell of
carbon has 4
electrons; can hold
8

• Each carbon atom

can form covalent
bonds with up to 4
atoms
Methane: Simplest Organic
Compound
H
Ball-and-stick
H C H model
H

Structural formula

Space-filling
model

Figure 3.2
Page 36
 Bonding Arrangements

• Carbon atoms can

form chains or rings

• Other atoms project

from the carbon
backbone Glucose
(ball-and-stick model)

In-text figure
Page 36
Hemoglobin Molecular Models

Ball-and-stick model Space-filling model

Figure 3.3
Ribbon model Page 37
 Functional Groups
• Atoms or clusters of atoms that are
covalently bonded to carbon backbone

• Give organic compounds their different

properties
 Question 1
1. How many single bonds does a carbon
form? What is the hybrid model that
applies? SP, SP2, or SP3 ?
 Answer 1
• How many single bonds does a carbon
form? What is the hybrid model that
applies? SP, SP2, or SP3 ?

Four bonds; SP3

Examples of Functional Groups

Methyl group - CH3

Hydroxyl group - OH
Amino group - NH3+
Carboxyl group - COOH
Phosphate group - PO4-
Memorize!
Sulfhydryl group - SH
 Question 2
2. Name three functional groups and give
their formulas.
 Answer 2
2. Name three functional groups and give their formulas.

Methyl group - CH3

Hydroxyl group - OH
Amino group - NH3+
Carboxyl group - COOH
Phosphate group - PO4-
Sulfhydryl group - SH
Types of Reactions (Stopped 17
aug 07)
Functional group transfer
Electron transfer
Rearrangement

Condensation
Cleavage
 Condensation Reactions
• Form polymers from subunits

• Enzymes remove -OH from one molecule,

H from another, form bond between two
molecules

• Discarded atoms can join to form water

Condensation

enzyme action at functional groups

enzyme action at functional groups

Figure 3.7a
Page 39
 Hydrolysis
• A type of cleavage reaction
• Breaks polymers into smaller units
• Enzymes split molecules into two or more
parts
• An -OH group and an H atom derived from
water are attached at exposed sites
 Hydrolysis

enzyme action at functional groups

Figure 3.7b
Page 39
 Carbohydrates
Monosaccharides
(simple sugars)

Oligosaccharides
(short-chain carbohydrates)

Polysaccharides
(complex carbohydrates)
 Monosaccharides
• Simplest
carbohydrates
• Most are sweet
tasting, water
soluble
• Most have 5- or 6-
carbon backbone

Structure of glucose
 Disaccharides
glucose fructose
• Type of
oligosaccharide
• Two
monosaccharides
covalently bonded + H2O

• Formed by
sucrose
condensation
reaction
Figure 3.8b
Page 40
 Polysaccharides
• Straight or
branched chains of
many sugar
monomers
• Most common are
composed entirely
of glucose

Starch chain
Figure 3.9
Page 40
 Cellulose & Starch

• Differences in bonding patterns between

monomers yield different properties

amylose (a starch)
cellulose

Figure 3.10
Page 41
 Glycogen
• Sugar storage form in animals
• Large stores in muscle and liver cells

Figure 3.10
Page 41
 Chitin
• Polysaccharide
• Nitrogen-containing groups attached to
glucose monomers
• Structural material for hard parts of
invertebrates, cell walls of many fungi
 Question 3
3. Name a common disaccharide. What are
its components (two sugars).
 Answer 3
3. Name a common disaccharide. What are
its components (two sugars).
• Sucrose. Glucose and fructose are its
component sugars.
 Question 4
4. Compare and contrast the meanings of:
disaccharide and polysaccharide
 Answer 4
• 4. Compare and contrast the meanings of:
disaccharide and polysaccharide.

• The former is composed of only 2

simple sugars. The later may be made
up of 100’s or 1000’s of simple sugars.
 Lipids
• Most include fatty acids
– Fats
– Phospholipids
– Waxes
• Sterols and their derivatives have no fatty
acids
• Tend to be insoluble in water
 Fatty Acids

• Carboxyl group at one

end
• Carbon backbone
• Saturated or
unsaturated

stearic acid oleic acid linolenic

Figure 3.12
acid
Page 42
 Fats

• Fatty acid(s)
attached to glycerol
• Triglycerides are
most common

Figure 3.13
Page 42
 Phospholipids

• Main component of
cell membranes
• Hydrophobic tails
• Hydrophilic head

Fig. 3.14a,b
Page 43
 Question 5
• 5. What are three categories of “fatty acid”
lipids?
 Answer 5
• 5. What are three categories of “fatty acid”
lipids?

– Fats
– Phospholipids
– Waxes
 Sterols and Derivatives
• No fatty acids
• Rigid backbone of
four fused-together
Cholesterol
carbon rings
• Cholesterol - most
common type in
animals Figure 3.15a
In-text p43
 Waxes

• Long-chain fatty acids linked to

long-chain alcohols or carbon rings
• Firm consistency, repel water

• Important in water-proofing
 Question 6
6. What are the characteristics of sterols?
Give an example.
 Answer 6
6. What are the characteristics of sterols?
Give an example.

• No fatty acids
• Rigid backbone of four fused-together
carbon rings
• Cholesterol - most common type in
animals
 Question 7
• 7. Describe waxes. Why are they
important?
 Answer 7
• 7. Describe waxes. Why are they
important?
• Long-chain fatty acids linked to long-
chain alcohols or carbon rings
• Firm consistency, repel water

• Important in water-proofing
 Amino Acid Structure

Carboxyl
group
Amino
group R group

Figure 3.16 tryptophan

Page 44 (trp)
Figure 3.17
Page 44
 Protein Synthesis

• Peptide bond
– Condensation reaction links amino group of
one amino acid with carboxyl group of next

Water forms as a by-product

Fig. 3.18a
Page 45
 Peptide bond forms.
Water forms as a by-product.

Another peptide bond forms.

Water forms as a by-product.

Another peptide bond forms.

Water forms as a by-product.

Another peptide bond forms.

Water forms as a by-product.
newly forming
polypeptide chain
 Primary Structure

• Sequence of amino acids

• Unique for each protein
• Two linked amino acids = dipeptide
• Three or more = polypeptide
• Backbone of polypeptide has N atoms:
-N-C-C-N-C-C-N-C-C-N-
 Second and Third Levels

• Hydrogen bonding
produces helix or
sheet
• Domain formation

Tertiary structure

Secondary Figure 3.19a

structure Page 46
 Fourth Level Structure

Some proteins
are made up of
more than one
polypeptide
chain

Figure 3.20 HLA-A2 quaternary structure

Page 47
 Hemoglobin
alpha chain beta chain

beta chain alpha chain

 One Wrong Amino Acid
• Single amino acid change in beta chain
can cause sickle-cell anemia

HbS

valine histidine leucine proline threonine valine glutamate

Fig. 3.21c,d
Page 48
 Sickle Cell Anemia
• Caused by two mutated copies (HbS) of
Hb gene
• Low oxygen causes red blood cells to
clump
• Clumping prevents normal blood flow
• Over time, may damage tissues and
organs throughout the body
 Myostatin
• Myostatin is a regulatory protein inhibits
muscle growth.

• One inactive myostatin gene will increase

muscle mass and reduce muscle fat.

• Two inactive myostatin genes will have a

dramatic effect on both muscle size and
fat content.
Myostatin Gene Inactivated
Belgium Blue Breed
 Beef Fat Content
• Meat from cattle having
no copies of the inactive
myostatin gene.
 One Inactive Myostatin Gene
• Meat from cattle having
one copy of the inactive
myostatin gene.
 Two Inactive Myostatin Genes
• Meat from cattle having two
copies of the inactive myostatin
gene.

http://www.ars.usda.gov/is/AR/archive/jul04/beef0704.htm
 "MIGHTY MOUSE" GENE
WORKS THE SAME WAY IN
•
PEOPLE
“Sequencing the
• myostatin gene from
• the boy and his
• mother, who had
• been a professional
• athlete, revealed a
• single change in the
• building blocks of the
• gene's DNA. Surprisingly,
• the change was not in the
• gene regions that correspond
• to the resulting protein,
• but in the intervening
• regions that are used only
• to create protein-making
• instructions, thus changing the
• gene's protein-building message.”

http://www.hopkinsmedicine.org/Press_releases/2004/06_23_04.html
 Loss of Myostatin Gene Builds
Muscle in Humans
• June 24, 2004Loss of Myostatin Gene Builds Muscle
in Humans

A research team funded by MDA has discovered a

naturally occurring genetic change (mutation) in humans
that dramatically increases muscle size and strength.
The mutation is in the gene for a protein called
“myostatin” that normally acts to slow muscle growth.
When this gene is inactivated, restraints on muscle
growth are lifted.

• http://www.mdausa.org/research/040624myostatin.html
 Double Muscled German Boy
• The researchers, led by
• Markus Scheulke of Charite
• University Medical Center
• in Berlin, identified a mutation
• in both copies of the myostatin gene in a 4-year
• old child who had been noted to have unusually
• well-developed musculature from the
• time of birth. At 4, the child was
• reportedly able to hold two 3-kilogram
• (6.5-pound) weights in his outstretched
• arms. His mother, a former professional
• athlete, was found to have a single copy
• of the same mutation.

http://www.ast-ss.com/blog/img/myostatin_boy.jpg
 Myostatin Serum Levels

“Measurement of myostatin
levels in the patient's serum
by electrophoretic
analysis showed absence
of the myostatin pepetide
in the child compared to
wild type organisms”

http://fig.cox.miami.edu/~cmallery/150/neuro/myostatin.htm
Selection?
 Nucleotide Structure

• Sugar
ATP
• At least one
phosphate group
• Nitrogen-
containing base

Figure 3.23a
Page 50
Nucleotide Functions
• Energy carriers
• Coenzymes

• Chemical messengers

• Building blocks for nucleic

acids
 DNA

• Double-stranded
• Sugar-phosphate
backbone
• Covalent bonds in
backbone
• H bonds between
bases

Figure 3.25
Page 51
 RNA

• Usually single strands

• Four types of nucleotides
• Unlike DNA, contains the base uracil in
place of thymine
• Three types are key players in protein
synthesis