Biological Molecules : The

Carbon Compounds of Life

Chapter 3
Learning Objec-ves (1 of 2)
1. Summarize the properties of carbon that have made it important for
the evolution of a wide diversity of organisms.
2. Describe how functional groups are important for the functions of
biological molecules.
3. Define isomer and state the relevance of isomers to biochemical
reactions.
4. Define a dehydration synthesis reaction and hydrolysis.
5. Differentiate between monosaccharides, disaccharides, and
polysaccharides, the different forms of carbohydrate molecules.
Learning Objec-ves (2 of 2)
6. Describe the structure and properties of lipids.
7. List major protein functions in living organisms.
8. Discuss the structure of amino acids, the formation of
polypeptides, and the four levels of protein structure.
9. Describe the structure of nucleotides and how they link together
to form DNA and RNA.
10. The structure of DNA and how it differs from RNA.
Regulatory Protein and DNA

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Organic Molecules
• Four major classes of organic molecules are found in living organisms:
carbohydrates, lipids, proteins, and nucleic acids
• In organic molecules, carbon atoms bond covalently to each other
and to other atoms in molecules that range in size from a few atoms
to thousands or millions of atoms
• Molecules consisting of carbon linked only to hydrogen atoms are
called hydrocarbons
• Hydrocarbons consist of carbon and hydrogen.
• Covalent bonds store considerable energy.
• Hydrocarbons are nonpolar. And when functional groups ARE ADDED,
THEY CONFER chemical properties to the molecule
 A. Two-carbon hydrocarbons with single, double,
and triple bonding

• Carbon has four unpaired outer

electrons
• The simplest hydrocarbon, CH4
(methane), consists of a single carbon
atom bonded to four hydrogen atoms B. Linear and branched hydrocarbon chains

• More complex hydrocarbons involve

two or more carbon atoms arranged
in a linear unbranched chain, a linear
branched chain, or a structure with
one or more rings
• Single and double bonds are found in C. Hydrocarbon ring, in this case with double bonds

linear and ring hydrocarbons; triple

bonds only in two-carbon
hydrocarbons
Functional Groups
Functional groups are small, reactive groups of atoms which give larger
molecules specific chemical properties
Functional groups that enter most frequently into biological reactions are
the hydroxyl, carbonyl, carboxyl, amino, phosphate, and sulfhydryl groups
Functional groups are linked by covalent bonds to other atoms in biological
molecules, usually carbon atoms – represented by the collective symbol R
Hydroxyl, Carbonyl, Carboxyl, and Amino
Groups
Phosphate and Sulfhydryl Groups
Isomers
Molecules with the same molecular or empirical formula but different molecular structures
1. Structural isomers – same chemical formula but arrangement of atoms are different
Example: glucose – aldehyde and fructose - Ketone
2. Stereoisomers – differ in how groups attached
Enantiomers - mirror image molecules, chiral carbon
Examples are D-sugars and L-sugars

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Stereoisomers

COOH COOH

H C R R C H

L isomer D isomer
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A. Glucose B. Fructose
(an aldehyde) (a ketone)

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H H H

H C OH C O C O

C O Structural H C OH Stereo- H C OH
isomer isomer
HO C H HO C H HO C H

H C OH H C OH HO C H

H C OH H C OH H C OH

H C OH H C OH H C OH

H H H
Fructose Glucose Galactose

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Biological Molecules – Proteins, Carbohydrates,
Lipids, and Nucleic Acids
• Polymer – built by linking monomers
• Monomer – small, similar chemical subunits

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

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Dehydration Synthesis
Hydrolysis
 Carbohydrates
• Molecules with a 1:2:1 raIo of carbon, hydrogen, oxygen
• Empirical formula (CH2O)n
• C—H covalent bonds hold much energy
• Monosaccharides contain three to seven carbon atoms
• Two monosaccharides polymerize to form a disaccharide
• Carbohydrate polymers with more than 10 linked
monosaccharide monomers are polysaccharides
• Energy storage molecules – glycogen and starch are
polysaccharides
• Structural carbohydrates example – Cellulose is a
polysaccharide
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 Monosaccharides

• Simplest carbohydrate
• 6 carbon sugars play important roles
• Glucose C6H12O6
• All monosaccahrides occur in linear form
• Example of common hexoses are Glucose, Fructose, and
Galactose
• Enzymes that act on different sugars can distinguish structural
and stereoisomers of this basic six-carbon skeleton

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Glyceraldehyde Ribose Mannose
(3 carbons; (5 carbons; (6 carbons;
a triose) a pentose) a hexose)

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• Monosaccharides with five or more carbons (such as glucose) can
fold back on themselves through a reaction between two functional
groups to assume a ring form
• Glucose exists as two different enantiomers
• α-glucose, with an —OH group pointing below the plane of the ring
• β-glucose, with an —OH group pointing above the plane
A. Glucose B. Formation of C. Simplified ring structure
(linear form) glucose rings

α-Glucose

or
D. Space-filling model

β-Glucose
 DISACCHARIDES
• Disaccharides are assembled from
two monosaccharides covalently
joined by a dehydration synthesis
reaction
• Example: Maltose is formed by a
glycosidic bond linking two α-
glucose molecules with oxygen as a
bridge between the 1 carbon of the
first glucose and the 4 carbon of the
second glucose unit – an α (1→4)
linkage
• Other common disaccharides
include sucrose (glucose + fructose)
and lactose (glucose + galactose)
 Polysaccharides
• Long chains of monosaccharides
– Linked through dehydration synthesis
– Polysaccharides may be linear, unbranched molecules, or they
may contain one or more branches in which side chains of
sugar units are attached to a main chain
• Energy storage
– Plants use starch
– Animals use glycogen
• Structural support
– Plants use cellulose
– Arthropods and fungi use chitin (modified glucose containing
nitrogen-containing groups)
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 AMYLOSE AND GLYCOGEN

A. Amylose, a plant
starch
Amylose, formed from

Ed Reschke/Getty Images
α-glucose units joined
end to end in alpha (1->4)
linkages. The coiled
structures are induced
by the bond angles in
the α -linkages.

Amylose grains (purple) in plant

root 2ssue

B. Glycogen, found in
animal tissues
Glycogen, formed
from glucose units joined
in chains by α( 1-> 4 )
linkages; side branches

DeAgostini/Getty Images
are linked to the chains
by α(1 ->6) linkages
(boxed in blue).

Glycogen par2cles (magenta) in

liver cell

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CELLULOSE
CHITIN, a reinforcing fiber in the external skeleton of arthropods
and the cell walls of some fungi

Beta (1,4 linkage)

 LIPIDS
• Lipids are water-insoluble, primarily nonpolar biological molecules
composed mostly of hydrocarbons
• Three common types of lipid molecules:
• Neutral lipids are stored and used as an energy source
• Phospholipids form cell membranes
• Steroids serve as hormones that regulate cellular acIviIes
Neutral Lipids
• Neutral lipids, found in cells as energy-storage molecules, have no charged
groups (nonpolar)
• There are two types of neutral lipids:
• Oils are liquid at biological temperatures
• Fats are semisolid
• A fatty acid contains a single hydrocarbon chain with a carboxyl group (—COOH)
at one end
 Glycerol and Triglyceride Formation
• Triglycerides form by
dehydration synthesis
between three-carbon
glycerol (an alcohol) and
three fatty acid side chains
• A covalent bond (ester
linkage) forms between the -
COOH group of the fatty acid
and the -OH group of the
glycerol
• The polar groups of glycerol
are eliminated, forming a
nonpolar triglyceride
Func-ons of Triglycerides
• Triglycerides serve as energy reserves in animals
• Store more than twice the calories per gram as carbohydrates
• A layer of fatty tissue just under the skin acts as insulation in
mammals and birds (e.g., penguins)
• Triglycerides also help make bird feathers waterproof
Saturated fats, Unsaturated fats, and Trans
fats
The most common fatty acids have chains of 14 to 22 carbons
• As chain length increases, fatty acids become less water-soluble and more oily
A saturated fatty acid binds the maximum number of hydrogen atoms
• Only single bonds exist between carbon atoms
• Saturated fatty acids are found in solid animal fats such as butter
Fatty acids with one double bond are monounsaturated; those with
more than on double bond are polyunsaturated
• Unsaturated fatty acids (such as vegetable oils) bend at a double bond and
are more fluid at biological temperatures

Unsaturated fats are more healthier than saturated fats

Fatty Acids
Trans Fat