Proper&es

of Macromolecules
Lecture 2

Overview
Proper&es of Carbon

Structure and Func&onal groups

Isomers

Polymers

Carbon: The Backbone of Life

Living organisms consist mostly of carbon-based
compounds
Carbon is unparalleled in its ability to form large,
complex, and diverse molecules
Proteins, DNA, carbohydrates, lipids, and other
molecules that distinguish living matter are all
composed of carbon compounds

Biomolecules range in size and

complexity
CO2
Carbon Dioxide

Large molecule
Phospholipid

CH4N2O
Urea

Macromolecules
DNA

C6H12O6
Glucose

Supramolecular Complex
Ribosome

Life exists even in harsh environments

Proper&es of Carbon
Contain carbon (C backbone)
Why is carbon so special?
Carbon can form 4 covalent bonds
bonds with up to 4 separate atoms
can bond with other C atoms

long chains of carbon atoms

can combine with many other kinds of atoms
Most contain H and O, but may contain other elements

N = Nitrogen

P = Phosphorus

S = Sulfur

Tetravalence in Carbon
Can form 4 single
bonds

2 double bonds

1 double bond and 2

single bonds

Carbon dioxide

1 triple bond & 1

single
Formaldehyde

Methan
e

C
H

H
H

Hydrogen Cyanide

C
H

Distinctive properties of an organic

molecule depends on:
1. Carbon skeleton
2. Functional
groups
molecular components
attached to the carbon
skeleton
responsible for
characteristic chemical
reactions of the
molecule

Together, these two characteris&cs give organic molecules

dis&nc&ve physical and chemical proper&es and creates diversity
among organic molecules

Carbon Skeletons
Made up of chains or rings
Skeletons differ in:
length (number of carbons)
branching
number and position of double bonds

 In molecules with multiple carbons, each carbon bonded to

four other atoms has a tetrahedral shape
When two carbon atoms are joined by a double bond, the
molecule has a flat shape

Hydrocarbons
Hydrocarbons: Organic
compounds composed only of
carbon and hydrogen (no
func&onal groups)
Covalent, non-polar bonds
between C & H
Nucleus
Fat droplets

Hydrocarbons are largely

hydrophobic
10 m
(a) Part of a human adipose cell

(b) A fat molecule

Func&onal Groups
Replacing H with func&onal groups changes
the characteris7cs of the molecule
Most func&onal groups form ionic or
hydrogen bonds with other molecules
Gives hydrophilic proper&es (water soluble)

*Some func&onal groups are non-polar and

may cause molecule to be hydrophobic

example:

These subtle variations in molecular architecture influence

development of anatomical and physiological differences

Func&onal Groups

Hydroxyl Group
R-OH or HO-R (R => remainder of molecule)
Hydroxyl groups are polar because
electronega&ve oxygen
Organic compounds having only hydroxyl
groups are called alcohols (ethanol,
methanol, etc.)
Sugars owe their solubility in water to the
presence of hydroxyl groups

Ethanol

Glucose molecule
(red=O, light gray= H)

Func&onal Groups

R-C=O

Carbonyl Group:
Aldehydes and Ketones

Polar carbonyl groups, such as aldehydes and ketones a`ract

covalent electrons
Aldehydes contain the carbonyl group bonded to the end of
the carbon skeleton
Ketones have the carbonyl group bonded within the carbon
skeleton

Func&onal Groups

Carbonyl Group:
Aldehydes and
Aldehyde
Ketones
Simple sugars can be
aldehydes or ketones

Ketone

Func&onal Groups

Carboxyl Group
R-COOH
Carboxyl groups are weakly acidic; in cells, this func&onal
group is found in the ionized form COO-
An important part of amino acids:

All amino acids contain a carboxyl group which can donate a hydrogen
aka. Carboxylic acid

Carboxyl Group examples

Other compounds that contain this functional group
include:
Formic acid a simple organic molecule released by
formicine ants (which account for about 10% of the
planets ants) as a defense mechanism
Acetic acid, gives vinegar its sour taste

Ace&c acid
Formic acid
h`p://www.youtube.com/watch?v=Sp8b1vVnQSY

 R-NH2

Func&onal Groups
Amino Group

Amino groups are weakly basic; under cellular condi&ons this

func&onal group is found in the ionized form NH3+
Also an important part of amino acids:

All amino acids contain an amino group which can accept a hydrogen

Func&onal Groups

Amino Group
Nitrogenous bases in
DNA and RNA contain
many amino groups

Func&onal Groups

Phosphate Group
R-PO4H2
Phosphate groups are weakly acidic; in cells, this func&onal group
contributes a nega&ve charge to the molecule
Phosphate groups are cons&tuents of:

Phospholipids
Phosphate group
contributes to the
polarity of the head
region

Func&onal Groups

Phosphate
Group

Nucleic acids (building

blocks of DNA and
RNA)
=> hence, sugar-
phosphate backbone
due to alterna&ng
sugar and phosphate

Func&onal Groups

Phosphate Group
Adenosine Triphosphate
Phosphate groups create instability in the molecule which is
responsible for its high energy state

Func&onal Groups

Sulhydryl Group
R-SH
Helps stabilize protein structure

When two sulhydryl groups

(func&onal group of amino acid
cysteine) within a protein are
facing each other, they oien
form a disulde bridge

CHEMICAL
GROUP

Hydroxyl

Carbonyl

Carboxyl

STRUCTURE
(may be written HO)
NAME OF
COMPOUND

Alcohols (Their specific names

usually end in -ol.)

Ketones if the carbonyl group is

within a carbon skeleton

Carboxylic acids, or organic acids

Aldehydes if the carbonyl group

is at the end of the carbon skeleton

EXAMPLE

Ethanol

Acetone

Acetic acid

Propanal
FUNCTIONAL
PROPERTIES

Is polar as a result of the

electrons spending more time
near the electronegative oxygen
atom.

A ketone and an aldehyde may be

structural isomers with different
properties, as is the case for
acetone and propanal.

Can form hydrogen bonds with

water molecules, helping dissolve
organic compounds such as
sugars.

Ketone and aldehyde groups are

also found in sugars, giving rise
to two major groups of sugars:
ketoses (containing ketone
groups) and aldoses (containing
aldehyde groups).

Acts as an acid; can donate an

H+ because the covalent bond
between oxygen and hydrogen
is so polar:

Nonionized

Ionized

Found in cells in the ionized form

with a charge of 1- and called a
carboxylate ion.

CHEMICAL
GROUP

NAME OF
COMPOUND
STRUCTURE

Hydroxyl
Amino
(may
be written HO)
Alcohols (Their specific names
usually end in -ol.)

(may be written HO)

EXAMPLE
Alcohols (Their specific names Thiols
NAME
OF
Amines
usually end in -ol.)
COMPOUND

Sulfhydryl Carbonyl

Phosphate Carboxyl

Ketones if the carbonyl group is

within a carbon skeleton

Methyl

Carboxylic acids, or organic acids

Aldehydes if the carbonyl group

is at the(may
end of
bethe carbon skeleton
written HS)
Ketones if the carbonyl group
is phosphates
Carboxylic acids, or organic acids
Organic
Methylated compounds
within a carbon skeleton
Aldehydes if the carbonyl group
is at the end of the carbon skeleton

EXAMPLE

Ethanol

Ethanol

Glycine

Cysteine

Acetone

Acetic acid

Acetone
Propanal

Acetic acid
Glycerol phosphate

5-Methyl cytidine

Contributes
negative
charge
to can donate an
as a base;
can of the
Two sulfhydryl
groups
Addition of a methyl group
FUNCTIONAL Acts
Acts as
an acid;
A ketone
andcan
an aldehyde
may be
Is polar
as a result
+ from the
+ because
the molecule of H
which
it is athe
part
up an Hspending
a covalent
to DNA, or to molecules
PROPERTIES pick
covalent bond
structural
isomers with different
electrons
more time react, forming
(2
when
at
the
end
of
a
molecule,
surrounding
solution
bond.
This
cross-linking
bound to DNA, affects the
between oxygen and hydrogen
properties, as is the case for
near the electronegative oxygen
as
above;
1
when
located
(water,
in
living
helps
stabilize
protein
expression of genes.
is so polar:
acetone and propanal.
atom.
internally in a chain of
organisms):
structure.
Arrangement of methyl
Can form hydrogen bonds with
Ketone and Propanal
aldehyde groups are
phosphates).
groups in male and female
water molecules, helping dissolve
also found in sugars, giving rise
sex hormones affects their

Cross-linking
of
cysteines

Molecules
containing
phosphate
organic
compounds
two major
groups
of sugars:
FUNCTIONAL
Acts
as an acid;
can donate an
Atoketone
and an
aldehyde
may
be have the
Is
polar as
a result of such
the as in hair proteins
shape and function.
maintains
groups
potential
to
react
sugars.
ketoses
(containing
ketone
PROPERTIES
H+ because the covalent bond
structural isomers with different
electrons spending more time
the curliness
or straightness
with water, releasing energy.
groups)
andasaldoses
(containing
between oxygen and hydrogen
properties,
is the case
for
near the electronegative oxygen
of hair. Straight
hair can
be
aldehydeand
groups).
isNonionized
so polar:
acetone
propanal.
atom.
Ionized
permanently curled by
Nonionized
Ionized
Can form hydrogen bonds withshaping it around
Ketone and
aldehyde groups are
curlers
water molecules, helping dissolve
also found
and then breaking
andin sugars, giving rise
Found in cells in the ionized form
Found
in cells
in the such as re-forming the
organic
compounds
to two
major groups of sugars:
cross-linking
with a charge of 1- and called a
ionized
form with a
sugars.
ketoses (containing ketone
bonds.
carboxylate ion.
charge of 1+.
groups) and aldoses (containing

Review

SH

Func&onal groups

H
N
H

Carboxyl
Amino

OH

Phosphate

C O

Carbonyl

O
C
OH

Sulfhydryl

O
O

P
O-

O-

Hydroxyl group

Isomers
Isomers are compounds with the same molecular formula (i.e. the
same numbers and types of atoms) but dierent structures and
proper&es.
Three important kinds for Biology:

1) Structural Isomers
Structural isomers have different covalent arrangements of
their atoms

2) Geometric Isomers
Geometric isomers have the same covalent
arrangements but differ in spatial arrangements
(arrangement around a double bond)

cis isomer

trans isomer:

Double bonds are rigid and do not allow the joined atoms
to rotate freely
As a result, two isomers are always possible if different
groups are attached around a double bond

Example: Rhodopsin
The visual pigment rhodopsin in the human eye
rotates around a double bond when hit by light at
the back of the retina

11-cis retinal

photon
All-trans retinal

3) Enan&omers
Enantiomers are isomers that are mirror images of each other
Usually consists of a carbon (i.e. asymmetric carbon) attached
to 4 different functional groups
L isomer

D isomer

Cells will recognize one enantiomer (i.e. biologically active)

but not the other

Example: Drug Enan&omers

Two enantiomers of a drug may have different
effects
This demonstrates that organisms are sensitive to
even subtle variations in molecules
Ex: L-Dopa

L-Dopa
(effective against
Parkinsons disease)

D-Dopa
(biologically
Inactive)

Macromolecules
Macromolecules are large molecules
composed of thousands of covalently
connected atoms
small organic molecules are joined together to
form larger molecules (aka polymers)
The architecture of a macromolecule helps
explain how that molecule works

Synthesis

Breakdown

Monomers form larger

molecules by condensa&on
reac&ons (dehydra&on
reac&ons)

Short polymer

Polymers are disassembled to

monomers by hydrolysis (the
reverse)

Unlinked monomer

Dehydra&on removes a water

molecule, forming a new bond

Hydrolysis adds a water

molecule, breaking a bond

Longer polymer

Requires: energy and catalyst

Occurs passively, but cells

use a catalyst

Synthesis and Decomposi&on

Reac&ons

4 Main Classes of Biomolecules

Polymer?

1. Carbohydrates

SOME

Monomer
MONOSACCHARIDE

2. Lipids

NO

3. Proteins

ALL

AMINO ACID

4. Nucleic Acids

ALL

NUCLEOTIDES

NA

Lecture 3: Learning Objec&ves

- Describe the importance of carbon in living organisms
- List and describe the two properties of Organic Compounds
- Know the structure, functions and give an example for the
main functional groups (hydroxyl, carbonyl, carboxyl, amino,
sulphydryl, and phosphate)
- Know the difference between structural isomers, geometric
isomers and enantiomers
- Understand dehydration and hydrolysis reactions
- Name the four classes of Macromolecules

Next Lecture:
Carbohydrates (ch. 3)