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Lecture 3: Cells and Small Molecules
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Goals:
1. Define prokaryote, eukaryote, carbohydrate,
polysaccharide, monosaccharide, fatty acid, amino acid
2. Understand specified complexity, the difference between
saturated and unsaturated fats, and the relationship
between chemical structure and biological function
3. Relate small molecule chemistry to heath, science, agriculture
and the environment.
Assignment:
Read: chapter 2, 6
Websites references:
http://esg-www.mit.edu:8001/esgbio/cb/prok_euk.html
http://www.cat.cc.md.us/courses/bio141/lecguide/unit1/u1i.html
http://www.lis.ab.ca/walton/omega/index.html
http://www-medlib.med.utah.edu/NetBiochem/FattyAcids/3_2
http://www-medlib.med.utah.edu/NetBiochem/FattyAcids/3_3.html
http://www.chem.pdx.edu/~wamserc/CH332S96/16notes.htm.html
http://vitawise.com/aminare.htm
http://www.harthosp.org/HealthInfo/scripts/scr0022.htm
http://www.americanheart.org/Heart_and_Stroke_A_Z_Guide/carbo
.html http://www.react.ie/Health/Nutrition/Carbohydrates.htm
Chapter 1:
Small Molecules
The 2nd Step in
understanding biology
is to begin to see the
Structure & Function of
Small Molecules…
“Nothing in life is to be feared, it
is only to be understood.”
-- Marie Curie (1867-1934)
French chemist and physicist,
Awarded 3 Nobel Prizes,
died of Cancer probably caused
brought on by the Radioisotopes (radiation)
she worked with!
Cells = The Basic
Building Blocks of Life
Two Classes of Cells:
Prokaryotes
-Mycoplasma
-Bacteria
Eukaryotes
-Protista, Animals,
-Fungi, Plants
Cells are expandable biological
factories that produce thousands of
different small and large molecules…
Possible CD on Cell Complexity
Cells Make Small Molecules
- Small molecules are assembled into large molecules
Carbohydrates and Polysaccharides
Made up of the following Elements =
Carbon, Oxygen, Hydrogen
Biological functions:
• energy storage, structure, signaling,
binding, adsorption, transportation…
Types of small molecules =
Carbohydrates
1. Sugar and Starches 2. Polysaccharide =
complex carbohydrate
Monosaccharides
(C:2H:O)n
1C:2H:1O
C H O H OH
HO
C
C
Glucose
C6O6H12
C H C
HO H C H OH
OH
Carbohydrates in the liver
Chemical structures
2-Dimensional View
Glucose
C H O H OH is the same as
HO
C
C
C H C
HO H C H OH
OH
3-Dimensional View
Disaccharides
Sucrose =
glucose + fructose
Maltose =
glucose + glucose
Lactose =
glucose + galactose
Molecular Complexity and
Specificity are Characteristics of
all living things
• A Glucose molecule is
simple compared to
DNA, but it is still
complex and specific.
• The difference between
Glucose and Galactose
molecules is only in the
positioning of the atoms
around the
ring…specified
complexity
glucose + galactose
= Lactose
The Following are all Glucose Monomers
Cellulose
Monomers
are one
Type of
Starch
molecule
Assembled
in long
Glycogen
Chains…
Chitin
Chapter 2:
Fats
Second part of
understanding small
molecules will be
Fats….
Small molecules: Fats
Elements = Carbon, Oxygen, Hydrogen
Less oxygen than
carbohydrates
COOH + (CH2)n
Fats belong to the organic compounds
(molecules) known as “Lipids”
Single fat molecule
Insoluble in water
Water
Carboxyl (COOH)
Hydrocarbon tail (CH)
Micelle
• Biological Functions of Fat
Long-Term
Energy Storage
Absorption
Energy
Supply
Transport
•Structure of fat = glycerol and fatty acids
Triglyceride = Another name for fats
1-Glycerol : 3- Fatty Acids
Glycerol
3- Fatty Acids
-C-CH2- CH2- CH2- CH2- CH2- CH2- CH3
||
O
-C-CH2- CH2- CH2- CH2- CH2- CH2- CH3
||
O
-C-CH2- CH2- CH2- CH2- CH2- CH2- CH3
||
O
Saturated fat = fatty acid contains all the
hydrogen bonds it can, or (in other words)
all carbon atoms have single bonds
H
H
H
H
H
H
H
H
H
H
H
H
H
H
H
H
H
H
H
H
H
H
H
H
H
H
O
O
H
O
H
Unsaturated fat = fatty
acid contains at least
one double bond H H
H
H
H
H
H
H
H H
H H
H
H
H
H H
H
H
H
H H
H
H
H
H
H
H
H
H
H O
H H
H
H H
Double bonds
Polyunsaturated fat = fatty acid has more
than one double bond
H
H H
H
O
H
H
H H
O
H H
H
More saturation = more risk of heart disease
Heart disease = location (site) of
double bonds and degree of
saturation
Fat-filled heart
-vegetable oils tend to be < saturated
than animal oils
Cholesterol: What is it?
Biological Function:
Low Density Lipoproteins - builds up on arterial walls.
• LDL Avoid red meats, hard cheese, egg yolks, and other high fat
dairy products and desserts. Avoid saturated fats, such as
fried foods, dressings, high-fat snacks, pastries, chocolate,
ice cream, and some candies
• HDL
• Ratio
High Density Lipoproteins - removes cholesterol from
artery walls to the liver for removal. Dietary fat >30% of
daily calories. To raise HDL’s, exercise regularly and eat
boiled, baked or steamed foods, low fat dairy, fish, poultry,
vegetables, exercise.
Divide the HDL cholesterol level into the total cholesterol.
Should be <5:1, though the optimal level is 3.5:1
• Arteriosclerosis
Thickening of the artery wall with fat
platelets
Protein
Fat
Site of the Saturation is the key to heart disease
Fish Oil
Red Meat Oil
Polyunsaturated Fatty Acids
Omega-3
•Omega-6 fatty acids are the
predominant polyunsaturated fatty
acids (PUFAs) in the Western diet.
•The omega-6 and omega-3 fatty acids
are metabolically distinct and have
opposing physiologic functions.
Omega-6
•The increased omega-6/omega-3 ratio
in Western diets most likely contributes
to an increased incidence of heart
disease and inflammatory disorders.
•Omega-3 PUFAs suppress cell
mediated immune responses and
reduce inflammation
Lipids in Cell Signaling
•Bioactive Lipids
•Made in all cells
•Short range signaling
•Eicosanoids?
•Prostaglandins
•Inflammation and Pain Perception
•Kidney Function
•Bone Development
•Reproductive Process
•Commercially Important
•$4 BILLION/ Year spend on drugs
to inhibit prostaglandin synthesis
•Vioxx, Celebrex, Ibuprofen, Asprin
PGE2
Site of the Saturation is the key to heart disease
Red Meat Oil
Fish Oil
Obesity in humans :
Some folks have
a genetic
condition
Normal Condition
White adipose tissue
Abnormal
Brown adipose tissue
Obesity in humans :
Fat Cells = Adipocytes
Some folks have
a genetic condition
Others eat too much
• just beneath the skin
• insulation
• capacity to change 100x
• permanent once created
• each person has a “set point”
-determines # lbs of fat the
will adjust back to…
US Adult Population averages = 35% body fat
Normal = < 20% body fat
Steroids = 4 Ring Phospholipid
Biological Function:
- coordinate physiological and behavioral responses for specific
biological purposes
What happens when folks take steroids?
• liver cancer, acne, heart attacks and strokes, arrested bone development
• withered testicles, sterility, impotence, gynecomastia (growth of breasts)
• in females. irreversible masculine traits can develop along with
menstrual irregularities, breast reduction, and sterility
• Psychological effects: aggressive, combative behavior known as "roid
rage“ and depression.
• Increase muscle mass, strength, endurance, recovery rates, muscle
definition, leanness
• Improved performance in sports, on the job, euphoria, sex drive
• Maintain and enhance appearance while aging
“Why should I be Clark Kent, when I can be Superman all the
time?” --Anonymous steroid user
Chapter 3: Peptide Structure:
peptide bonds and side
chains
Third part of
understanding small
molecules: peptides
Small molecules: Amino Acids (AA)
The building blocks of proteins
• Elements = Carbon, oxygen, hydrogen,
nitrogen, (sometimes sulfur)
• More nitrogen than sugar or fats contain
• Proteins = Chains of Amino Acids
• Structure is dependant
upon = side chain(s)
Amino Acid Structure
Amino
group
H
N
H
Carboxyl
group
R
-Central carbon
atom
-Carboxyl group
C
-Amino group
H
C
O
OH
-Side chain (R)
-Hydrogen atom
Side chains (R groups) determine 20 different amino acids
H2N
NH
Side Chains: “R”
HN
NH
O
O
O
CH3
HN
O
CH2
CH2
HO
CH3
CH2
CH2
H2NC
CH2
O
HO
H
N
H
C
O
C
2
2
H NH
CH
CH2N O
H
N
CH
H
H2C
2
H2N C
O
2
C
2
O O
H2N H
CH
H
H
H2N
H2N
H2N
O
C
2 CO
HN OH
O
OH
H
H
N
CH3
OH
H CH
2
OH
O HC2N HO
OH CH2 NH
H
O
2
H
H2N H N
|H C
OH HN
CH2
C
O O
OH
O
C
2
2
H
CH
CH
CH2 HO
OH
H2N H CH2
2
O3
C
Asparagine
Arginine
Glycine
CH2 Alanine
H2N
H2NO H C
OH
O Asparagine
H2AN
C
Aspartic
H2C OH
C
O
Arginine
H
AlanineO H
H
N
H
Asparagine
H2N
2 OH
CH2 Aspartic Ac
C H2N
H2N H
HN
OH HO
C
OH H N 2 OH O
Arginine
HS
O
O
CH
H
O
H
2
OH
2
HS
O
O H2N
CH
2Arginine
lanine
H2
C
O
H2C Asparagine
H2C
Aspartic Acid
OH
H
HC2
CH2
CH2N O
H2C
CH2
H2C
H
H
CH2
CH2
Arginine H2N C
2N
Asparagine
Alanine
H
N
Aspartic
Acid
H
O
CH
C
C
O
O
2
Cysteine
Glutamine
3
H2N
O
H
CH2
CH3
C2N H O O
H2N
OH
C H O
H
H
H2N
H2N
NH
OH
H2NH2
C
OHO
H
C
OH
OH
O
H
C
HS
O 2
2
O
H
CH2
OH CH2 CH2 Glutamic
OH AcidC
O
OCysteine
Glycin
Glutamine
H
N
H2
Glycine
2 H C
CH
Acid
HO
2
CH3 H2CCysteine C
O
C2 C
O Glutamine
O Glutamic
2
C H NO H N H
H2
CH2
2H2NCH
OH
HCH
N
2 C 2
O
2
H
N
2
CH2
C Acid
H2N H
OC OH
Glutamic
Aspartic
AcidOH CH
O
C
O
3
H
HN HN H
OH
HN H
H3C
CHS3
HH
CH CH3
2C
2 C
CH2
CC OO
Isoleucine
H2N HH
H2N
CH3OH
OH
C
Isoleucine
H3C Methionine
H CH2
H
C H
CH N
C
HC
H2
C
HC HN
CH
CH
2
C C
2
H2C
H H
C CO O
N
H
H
H
N
Histidine
H2N 2
H
OH OH
H3C H CH
2
H2
C
C
H
C
H2N H
O
O
HO
OH C
C
Leucine
H2N H
OH NH2
H2C
H
Histidine
CH2
Phenylalanine
H3C
C
Proline
Se
CH
H H S
HC
H2C
C C
C
O
CH2
HC
H
C
H
HLeucine
N
H
CH
2
2
C C
CH2
3 CH
HC
CH
H
O
OH
CH
2
C
H
C
2C
H
H
Lysine
OH
3
H
C
H
CH
H
OH
C
2
O
C
H2N
H3C H
C 3 O
C
H
CLeucine
Methionine
HC
H2CH
N
H
H2N H
H
N
OH
C
2
C
C
CH
C
O
H
O
C
2
C
H2N H
OH
Lysine
HC H CHH
H
H
N
C
H
N
O
H
OH
H2
2
2 H
HO H
Threonine
HNH
C 2 O
C
2N 2
HPhenylalanine
C
C
NH
Methionine
CH2
2N
C
H
C
H
H
N
OH
O
CH
CH
S
2
H
C
C
OH
H
CH
2
CH2
2
H HCH
2 H
OH
O O
HN H2C
CH2 H
2 O
C
O
C
C
OH
CH3 HC C
CH2 CH
Isoleucine
OCH CHTryptophan
H2N H
N HC C
Tyrosine
CH2C O H CThreonine
H
O
2
2V
H
C
2
CH2 2
H
N
H
H
C
H
C
H
CH C HO
O
CH2
CCH 2O H
2
H
N
H
C
C
O
OH
C
2
OHH
H 2
C 2 CH
O
H2N
H
H
N
N
OH
C
O
OH
H2N H
Alanine O H N H
H32C H H
O 2 Serine
C
OH
Proline
H
C
H2N
2
C
HC
H
H
N
OH
OH
H
H
N
2
hionine
C
OH
OProline
O
H2N Phenylalanine OH
Serine
CH
H
O
C
2
OH
C
HN
OH
OH
lanine
Proline
enylalanine
Proline
H
H
C
H
C
H
HO
C
CH
HO CH
CH
Serine
Serine
H3C H CH3
HC3C H CH3
C
HC
H H
CC CH2 CH
C
O
CH2
C
C
2
H
C
H
H
N
O
CH HC
CHH
O
H22 HH N H
2C
HO
2 2
OC
H C
C
O
H
N
CH2
2
OH
C
H
H C HCO C
CHH
N
Tyrosine
Valine
22
OH
H2N H
OH H2C
C
H
O
C
O
C
O
H
H
N
OH
OH
N
H
O
2
H
H
Valine
tophan OH H2N Tyrosine
Tyrosine
OH
Tryptophan
OH Valine
H
ne
OH
Phenylalanine
H H
C CH C
3
HC
CH S
H
O
H
ine
HN
H2C
CH2
C
H
C
H2N H
Proline
H
C
HO
CH2
O
C
H2NOHH
Tryptophan
Tryptophan
HC
O
OH
H
C
HC
CH
C
H
Serine
CH
HC
CH2
C
C HO
H3C H CH3
C
CH2
C
H2N H
C
H2N H
Phenylalanine
OH
H2N H
Tyrosine
O
HO2C
OH
OHValine
H2 H
C C2
C
N H
H
OH
Essential Amino Acids = 9
Biological Function:
The essential building blocks for all proteins of life
Histidine
Isoleucine
Leucine
Lysine
Methionine
Phenylalanine
Threonine
Tryptophan
Valine
Assignment: What do the essential amino acids do?
Examples of 3 Essential Amino Acids
Alanine
Cysteine
Serine
Key Review of Small Molecules
•
•
•
•
•
•
•
Eukaryote
Carbohydrate
Polysaccharide
Monosaccharide
Fatty acid
Amino acid
Prokaryote
• Difference between saturated
and unsaturated fats
• Relationship between
chemical structure and
biological function
• Living chemistry is both
complex and specified
• Relate small molecule
chemistry to heath,
science, agriculture and
the environment