Introduction to Cell Biology

Lecture #2: bonds, chirality, sugars and lipids

Marcelo Ehrlich, PhD
Department of Cell Research and Immunology
2014
1
4 types of chemical bonds
- covalent = two atoms share electrons
- ionic = based on the electrostatic forces between two
oppositely charged ions
- hydrogen = attractive interaction (dipole-dipole) between an
electronegative atom and an hydrogen atom bound to another
electronegative atom
- Van der waals= intermolecular forces which arrisefrom the
generation (transient) of dipoles
2
Bond angles Bond angles
Bond rigidity
3 How do chemical bonds contribute to molecular shape?
The form forming potential of carbon skeletons
Chains Branched trees
Rings
4
The function of molecules is determined by
their shape
The shape of molecules is determined by
the chemical bonds of the atoms which form
it.
Chemical bonds can be defined in terms of
their strength, polarity, angles and rigidity

?
5
0.27nm
Figures 2-10, 2-14, Panel 2-2
water (H
2
O)
Water: the medium in which life started and the medium in
which life takes place. What are the characteristics of water that
contribute to the process of life?
+
+
2-
+
+
2-
6
Panels 2-2, 2-7
1998 and 2004 GARLAND PUBLISHING
7
Figures 5-2, 5-6
2004 GARLAND PUBLISHING
8
, MELTING AND ANNEALING
9
-helix
Figure 4-10
2004 GARLAND PUBLISHING
Denaturation
Renaturation
Folded state
Random coil
10
heat
alcohol
denaturing agents (urea)
?
11
Isomere = from the Greek isos= equal and mere = part
Compounds with the same molecular formula but with different
structural formulae
Some definitions:
Stereoisomere: the atoms
are joined in the same way
but have a different spatial
arrangement
Structural isomere: the
atoms are joined in different
ways
C-C-C
H
H
H
H
H H
H
OH
C-C-C
H
H
H
H
H H
H
H
O
Enantiomeres
Enantios = opposite
Mirror images of one
another
12
asymmetric carbon =
chiral center
Chirality
13
L-aspartyl -L-phenylalanine methyl ester L-aspartyl -D-phenylalanine methyl ester
sweet bitter
14
2
Carbo - Hydrates
monomer polymer
15
Chiral center - D configuration
Aldehyde
C
C
C
O
OH
H
OH
H
2
H
Glyceraldehyde - the smallest sugar
(CH
2
0)
3
Carbo - Hydrate =
16
glyceraldehyde ribose glucose
fructose
hexose
ribulose dihydroxyacetone
triose pentose
aldose
ketose
Panel 2-3

2
0
0
4

G
A
R
L
A
N
D

P
U
B
L
I
S
H
I
N
G
17
CH
2
OH
1
2 3
4
5
6
OH
O
H
CH
2
OH
1
2
3
4
5
6
O
CHO
CH
2
OH
1
6
CH
2
OH
1
6
CHO
L -glucose D -glucose
OH

OH
anomeric carbon
Figure 2-16
2004 GARLAND PUBLISHING
18
2004 GARLAND PUBLISHING
CHO
CH
2
OH
1
6
D -glucose
glucose
CHO
CH
2
OH
1
6
D -galactose
galactose
CHO
CH
2
OH
1
6
D -mannose
mannose
Panel 2-3
Epimers of glucose
Epimer= a stereoisomer that has a different configuration at only one
stereogenic center and are not mirror images of each other.
19
RNA

3OH+2OH in RNA
3OH+2H in DNA
3H+2H=
dideoxynucleotide
20
Figure 2-28
2004 GARLAND PUBLISHING
condensation
hydrolysis
21
Panel 2-3
2004 GARLAND PUBLISHING
glucose
fructose
sucrose
22
Figure 2-20
2002 GARLAND PUBLISHING
23
2004 GARLAND PUBLISHING
Figure 13-18,20
24
1-4
1-4
glycogen, starch
cellulose
25
26
27
Figure 2-15
2004 GARLAND PUBLISHING
monomer polymer
- Structural component of membranes (essential for
compartmentalization)
- Storage (energy, fat)
- Intracellular signaling
28
Fatty Acids
- Long chain (even number of carbons),
mono-carboxylic acids, that have a general
structure of
CH
3
(CH
2
)
n
COOH
- Saturated (no double bonds) or unsaturated
29
palmitic acid - 16 carbons
Figure 2-18
2004 GARLAND PUBLISHING
Hydrophilic carboxylic acid head
Hydrophobic hydrocarbon tail
30
18 carbons
stearic acid vs. oleic acid
saturated unsaturated
Panel 2-4
2004 GARLAND PUBLISHING
31
32
33
Panel 2-4
2004 GARLAND PUBLISHING
ester bonds
Glyceridesare lipids possessing a glycerol core structure
with one or more fatty-acyl groups attached by ester
linkages.
Trygliceridesare the main storage form of fat
34
Glycerophospholipids
Glycerol linked to two fatty acids (tails) and
one phosphate-based (head). Common
phospholipids in cell membranes are
phosphatdyl-choline, phosphatdyl-serine,
phosphatdyl-ethanolamine, phosphatdyl-
inositol.
35
phosphatidylethanolamine cholesterol phosphatidylserine
Figures 11-7
2004 GARLAND PUBLISHING
36
Figure 2-20
2004 GARLAND PUBLISHING
lipid bilayer
micelle
37