SMBM 102

INTRODUCTION TO THE HUMAN BODY

BIOCHEMISTRY

JERRY QUAYE
Recommended Textbooks

1. Berg, J. M., Tymoczko, J. L., Gatto, G.J., & Stryer, L. (2019). Biochemistry (9th
Ed). New York: W H. Freeman & Company.
2. Da Poian, A.T., and Castanho, M.A.R.B. (2015). Integrative Human
Biochemistry. New York: Springer Science+ Business Media LLC.
3. Devlin, T. M. (2010). Textbook of Biochemistry with Clinical Correlation (7 th
Ed). New York: John Wiley & Sons.
4. Harvey, R.A., and Ferrier, D.R. (2011). Lippincott’s Illustrated Reviews-
Biochemistry (5th Edition). Baltimore: WoltersKluwer/Lippincott Williams &
Wilkins.
5. Kennelly P.J., & Botham K.M., & McGuinness O.P., & Rodwell V.W., & Weil
P(Eds.), (2023). Harper's Illustrated Biochemistry, 32e. McGraw Hill.
https://accessmedicine.mhmedical.com/content.aspx?bookid=3220&sectionid=268188332
6. Nelson, D.L., and Cox, M.M. (2017). Lehninger principles of Biochemistry (7th
Edition). W.H. Freeman, New York.
7. Rae, P., Crane, M., and Patttenden, R. (2017). Clinical Biochemistry (10th
Edition). New York: John Wiley & Sons.
8. Rodwell, V., Bender, D., Botham, K.M., Kennelly, P.J. and Weil, P.A. (2015).
2
Harper’s Illustrated Biochemistry (30th Edition). McGraw-Hill Medical.
 Lipids
• Like carbohydrates, lipids contain carbon,
hydrogen, and oxygen. Unlike carbohydrates,
they do not have a 2:1 ratio of hydrogen to
oxygen.
• The proportion of oxygen atoms in lipids is
usually smaller than in carbohydrates, so there
are fewer polar covalent bonds.
• As a result, most lipids are hydrophobic; that
is, they are insoluble in water.
 Cont… lipids
• The diverse lipid family includes triglycerides
(fats and oils), phospholipids (lipids that
contain phosphorus), steroids, fatty acids, and
fat-soluble vitamins (vitamins A, D, E, and K).
• Triglycerides are the body’s most highly
concentrated form of chemical energy, storing
more than twice as much chemical energy per
gram as carbohydrates or proteins.
 Cont… lipids
Lipids are
• Biomolecules that contain fatty acids
or a steroid nucleus.

• Soluble in organic solvents but not in

water.

• Extracted from cells using organic

solvents.

5
 Types of Lipids

The types of lipids containing fatty acids

are:
• Waxes
• Fats and oils (triacylglycerols)

• Glycerophospholipids

• Prostaglandins
Not steroids, as they do contain fatty acids
6
Structures of Lipids

 Carboxylic Acids (COOH is C1)

 hydrocarbon tails (C4 - C36)

 Saturated fatty acids no double bonds

 Unsaturated Fatty acids presence of double

bonds

 Double bonds specified by (Δn)

7
Types of Lipids

8
 Fatty Acids
Fatty acids
• Are long-chain carboxylic acids.

• Typically contain 12-18 carbon

atoms.

• Are insoluble in water.

• Can be saturated or unsaturated.

9
 Fatty Acid Formulas
The formulas for fatty acids are written as
• Condensed formulas.

• Line-bond formulas.

• For example caprylic acid with 8 carbon atoms.

CH3—(CH2)6—COOH

CH3—CH2—CH2—CH2—CH2—CH2—CH2—COOH
O
10
OH
 Saturated Fatty Acids
Saturated fatty acids have
• Single C–C bonds.
• Molecules that fit closely
together in a regular
pattern.
• Strong attractions
between fatty acid
chains.
• High melting points that
make them solids at
room temperature.
11
Unsaturated Fatty Acids

12
 Prostaglandins
Prostaglandins have
• 20 carbon atoms in their fatty acid
chains.
• An OH on carbon 11 and 15.
• A trans double bond at carbon 13.

C 13

C 11 C 15
14
 Prostaglandins in the Body
Prostaglandins are
• Produced by injured
tissues.

• Involved in pain, fever

and inflammation.

• Not produced when

anti-inflammatory
drugs such as aspirin
inhibit their synthesis.

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 Omega-6 and Omega 3- Fatty Acids
Fatty acids
 In vegetable oils are mostly omega-6 with
the first C=C at C6.
linoleic acid

CH3─(CH2)4─CH=CH─CH2─CH=CH─(CH2)7─COO
H 6

 In fish oils are mostly omega-3 with the

first C=C at C3.

linolenic acid
CH3─CH2─(CH=CH─CH2)3─(CH2)6─COOH
3 16
Waxes, Fats, and Oils

17
 Waxes
Waxes are
• Esters of saturated fatty acids
and long-chain alcohols.
• Coatings that prevent loss of
water by leaves of plants.

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 Fats and Oils: Triacylglycerols
Fats and oils are
• Also called triacylglycerols.

• Esters of glycerol.

• Produced by esterification.

• Formed when the hydroxyl

groups of glycerol react
with the carboxyl groups of
fatty acids.
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 Triacylglycerols

In a triacylglycerol,
• Glycerol forms ester bonds
with three fatty acids.

20
 Formation of a Triacylglycerol
glycerol + three fatty acids triacylglycerol

O
CH2 OH HO C (CH2)14CH3
O
CH OH + HO C (CH2)14CH3
O O
CH2 OH HO C (CH2)14CH3 CH2 O C (CH2)14CH3
O
CH O C (CH2)14CH3 + 3H2O

O
CH2 O C (CH2)14CH3
21
 Olive Oil
Olive oil
• Contains a high
percentage of
oleic acid, which
is a
monounsaturate
d fatty acid with
one cis double
bond.

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 Identify the constituent units in the
molecule
Name the molecule
O
CH2 O C (CH2)16CH3
O
CH O C (CH2)7CH CH(CH2)7CH3
O
CH2 O C (CH2)12CH3

23
 Melting Points of Fats and Oils
A triacylglycerol that is a fat
• Is solid at room temperature.
• Is prevalent in meats, whole milk,
butter, and cheese.

A triacylglycerol that is an oil

• Is liquid at room temperature.
• Is prevalent in plants such as olive
and safflower.
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 Oils with Unsaturated Fatty Acids

Oils
• Have more unsaturated fats.
• Have cis double bonds that cause
“kinks” in the fatty acid chains.
• Cannot pack triacylglycerol
molecules as close together as in
fats.
• Have lower melting points than
saturated fats.
• Are liquids at room temperature.
25
Diagram of Triacylglycerol with
Unsaturated Fatty Acids

Unsaturated fatty acid

chains have kinks that
do not allow close
packing.

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 LIPIDS
Circulatory lipids Structural Lipids
(Cellular Membrane)
1. Free Fatty Acids 1. Phosphatidylinositol
(FFAs)
2. Phosphatidylcholine
2. Triacylglycerol (TAG)
3. Sphingomyelin
3. Cholesterol
4. ceramide.
4. Cholesteryl ester
N.B: They are derived from
5. Phospholipids the circulatory lipids

6. Lipoproteins 27
 Circulatory Lipids

Free Fatty Acids

Fatty acids consist of a hydrocarbon chain with a carboxylic
acid at one end.

A 16-C fatty acid: CH3(CH2)14 -COO-

Non Polar Polar
Fatty Acids

Saturated Unsaturated
1. Liquid at room temperature
1. Solid at room temperature 2. Presence of double bonds
2. Absence of double bond 3. Monounsaturated or
Polyunsaturated
3. Found in fats
4. 16-C fatty acid with one cis double
bond between C atoms 9-10 may be
represented as 16:1 cis ∆9.
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5. Found in Oils
 Free Fatty Acids

Two Types:
1. Non- Essential Fatty Acids: Can be
synthesized by the body

2. Essential Fatty Acids: Supply through food

Essential Fatty Acids (EFAs): Physiology and
Clinical Significance

Examples: Linoleic and Linolenic acids

 Are essential for the brain growth and

development of humans

 EFAs form precursors to various prostaglandins

29
(PGs), thromboxanes (TXs), leukotrienes (LTs).
 Triglycerides
 In human nutrition, triglycerides constitute 95% of
tissue storage fat and are the predominant form of
glyceryl ester found in plasma.

 Made up of three fatty acids moieties and

glycerol.

 The fatty acid residues found in (monoglycerides,

diglycerides or triglycerides) vary considerably
and usually include combinations of the long-chain
fatty acids.

 Stores chemical energy in a water free and

compact state (Adipose tissue) 30
 Triglycerides

Glycerol Esters:
Triglycerides, diglycerides, and
monoglycerides (acyleglycerol).

Phosphglycerides- precursor of
complex lipids

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 Cholesterol Cycle
Cholesterol synthesized
Diet De novo synthesis
in extrahepatic tissues

Liver cholesterol
pool

Conversion to bile
Secretion of HDL Free cholesterol salts/acids
and VLDL In bile
32
 Lowering Cholesterol
Oat bran
 Soluble fiber
 Bind bile acids

Niacin
 Inhibits VLDL excretion ? (fatty liver)
 Flushing and liver damage

Statins –
• decrease HMG CoA reductase
activity

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 Cholesteryl Ester
• Cholesterol esterified with
fatty acid.

• It forms about 10-15%

of dietary cholesterol.

• Cholesteryl esters are

the intracellular storage
form and intravascular
transport form of
cholesterol.

• It exists in crystal and liquid states.

34
 Lipoproteins

 Lipids must be transported to the various tissues to

accomplish their metabolic functions.

 Because of their insolubility, they are transported in

plasma in macromolecular complexes called
Lipoproteins.

Chemistry:
 Lipoproteins are spherical particles with non polar
lipids (triglycerides and cholesterol esters) in their
core and more polar lipids (phospholipids and free
cholesterol) oriented near the surface.

 They also contain one or more specific proteins

called apolipoproteins, that are located on their 35
 Basic Structure of Lipo-
proteins
Lipoprotein Lipoprotein
• LP core
– Triglycerides
– Cholesterol esters

• LP surface
– Phospholipids
– Proteins
– cholesterol

36
 Types of Lipoproteins

Chylomicrons Lipoproteins
– Synthesized in small
intestine
– Transport dietary
lipids
– 98% lipid, large sized,
lowest density

37
Functions of the lipopro-tein Types

Functions Lipoproteins

Transport of exogenous triglyceride Chylomicrons

Transport of endogenous triglyceride VLDL

Transport of cholesterol from liver to LDL

other tissues
Transport of cholesterol from HDL
peripheral tissues and other
lipoproteins to liver
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 Functions of Apolipoprotein

 They serve to solubilise plasma lipids.

 Activate enzymes involved in lipid

metabolism (LCAT, LPL).

 Maintain structural integrity of

lipid/protein complex.

 Delivery of lipids to cells via recognition of

cell surface receptors.

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Chemical Properties of Triacylglycerols

The chemical reactions of

triacylglycerols are similar to those
of alkenes and esters.
• In hydrogenation, double bonds in
unsaturated fatty acids react with H2
in the presence of a Ni or Pt catalyst.

• In hydrolysis, ester bonds are split by

water in the presence of an acid, a
base, or an enzyme.
40
 Hydrolysis
In hydrolysis,
• Triacylglycerols split into glycerol
and three fatty acids.
• An acid or enzyme catalyst is
required.
O
CH2 O C (CH2)14CH3
O
H+
CH O C (CH2)14CH3 +3H2O
O
CH2 O C (CH2)14CH3 CH2 OH
O
CH OH + 3 HO C (CH2)14CH3
41
CH2 OH
 Saponification and Soap
Saponification
• Is the reaction of fat with strong base.

• Splits triacylglycerols into glycerol and

the salts of fatty acids.

• Is the process of forming “soaps” (salts

of fatty acids).

• With KOH gives softer soaps.

42
 Saponification
O
CH2 O C (CH2)14CH3
O
CH O C (CH2)14CH3 + 3NaOH

O CH2 OH
CH2 O C (CH2)14CH3

CH OH O
+ 3 Na+ -O C (CH2)14CH3
CH2 OH “soap”

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Phospholipids
 Glycerophospholipids
Glycerophospholipids are:
• The most abundant lipids in cell
membranes.
• Composed of glycerol, two fatty acids,
phosphate and an amino alcohol.
Fatty acid

Fatty acid
Glycerol

Amino
PO4
alcohol

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 Glycerophospholipids
Lecithin and cephalin are glycerophospholipids
• Abundant in brain and nerve tissues.
• Found in egg yolk, wheat germ, and yeast.

Platelet
activated

46
 Glycerophospholipids
O

O H2 C O C R2

R1 C O CH O

H2 C O P O

O H

OH OH
H OH
OH H
phosphatidyl- H H
inositol
H OH

Phosphatidylinositol, with inositol as polar head group,

is one glycerophospholipid.
In addition to being a membrane lipid,
phosphatidylinositol has roles in cell signaling.
47
Glycerophospholipids Are Polar
A glycerophospholipid has
• Two nonpolar fatty acid chains.
• A phosphate group and a polar amino alcohol.
CH3
│+ +
HO−CH2−CH2−N−CH3 HO−CH2−CH2−NH3
│
choline CH3 ethanolamine

+
NH3
│ Amino alcohols
HO−CH2−CH−COO−
48
serine
Structure and Polarity of A
Glycerophospholipid

49
 Sphingolipids
Sphingolipids
• Are similar to phospholipids.
• Contain sphingosine (a long-chain
amino alcohol), a fatty acid,
phosphate, and a small amino
alcohol. fatty acid

• Have polar
sphingosine
and nonpolar regions.

amino
PO4
alcohol
50
 Sphingosine

Sphingosine is a long-chain unsaturated amino

alcohol.

CH3−(CH2)12 −CH=CH−CH−OH
│
CH−NH2
│
CH2−OH

sphingosine
51
 Sphingolipids
• In sphingomyelin, a sphingolipid found in
nerve cells
• There is an amide bond between a fatty
acid and sphingosine, an 18-carbon
alcohol.

52
 Glycosphingolipids

• Glycosphingolipids
contain
monosaccharides
bonded to the –OH of
sphingosine by a
glycosidic bond.

53
Glycosphingolipids and Cerebrosides

Glycosphingolipids
• Are sphingolipids that contain
monosaccharides.
• Can be a cerebroside with
galactose.

54
 Gangliosides
Gangliosides
• Are similar to cerebrosides, but contain
two or more monosaccharides.

• Are important in neurons.

• Act as receptor for hormones and

viruses.

• Can accumulate and cause genetic

diseases.

55
Steroids: Cholesterol, Bile Salts, and
Steroid Hormones

CH3 CH3
CH3
CH3
CH3

HO

56
 Cholesterol

Cholesterol
• Is the most abundant steroid in the
body.
• Has methyl CH3- groups,
CH3 alkyl chain,
CH3
CH3
and -OH attached to the steroidCH
3
nucleus. CH3

HO

57
 Lipoproteins
Lipoproteins
• Combine lipids with proteins and
phospholipids.
• Are soluble in water because the surface
consists of polar lipids.

58
 Types of Lipoproteins
Lipoproteins
• Differ in density, composition, and function.
• Include low-density lipoprotein (LDLs) and
high-density
TABLE 17.5
lipoprotein (HDLs).

59
Glycolipids and cell membrane
functions

60
 Cell Membranes
Cell membranes
• Separate cellular contents from the
external environment.

• Consist of a lipid bilayer made of two

rows of phospholipids.

• Have an inner portion made of the

nonpolar tails of phospholipids with the
polar heads at the outer and inner
surfaces.
61
Functions of Glycolipids

 Membrane receptors for virus. Eg: rubella

virus

 It acts as a recognition site for specific

chemicals / proteins.

 Helping maintain the stability of the

membrane

 Help attach cells to one another to form

tissues.

 Heat shock response eg: Cholesteryl

glucoside

 Insulation of myelin 62
Fluid Mosaic Model of Cell Membranes

The lipid bilayer

• Contains proteins, carbohydrates,
and cholesterol.
• Has unsaturated fatty acids that
make cell membranes fluid-like
rather than rigid.
• Has proteins and carbohydrates on
the surface (receptors) that
communicate with hormones and
neurotransmitters.
63
Membrane lipids protect cells

64
NUCLEIC ACIDS
What are nucleic acids?
The nucleic acids, deoxyribonucleic acid
(DNA) and ribonucleic acid (RNA) are polymers
of nucleotides.

The genome is the entire sequence of a cell’s

DNA (or in the case of RNA viruses, its RNA), and
genomics is the characterization of the
structure, function, evolution, and mapping of
genomes.
 Nucleic Acids
• Nucleic acids are polymers

• Monomer---nucleotides

– Sugar (five carbon sugars)

• Ribose
• Deoxyribose

– Nitrogenous bases
• Purines
• Pyrimidines

– Phosphates
67
 Continued
Nucleic acids make up 13-34% of the dry weight in bacteria

Nucleotide: a building block

OH
Nucleoside: base + sugar
HO P O CH2 Base
Sugar: O
• RNA – ribose (OH) O C H H C
• DNA – deoxyribose (H) C C H
H
Bases: HO H or OH
• adenine (A), cytosine (C), guanine (G),
thymine (T)
• RNA uses uracil (U) instead of thymine
Certain nucleotides serve as a storage of energy and reducing power
e.g. ATP -> ADP -> AMP

hydrolysis (energy is released) 68

The Sugars

69
 The Bases

Pyrimidines

Purines

70
 Nucleosides
BASE NUCLEOSIDE DEOXYNUCLEOSIDE

Adenine Adenosine 2-deoxyadenosine

Guanine Guanosine 2-deoxyguanosine

Cytosine Cytodine 2-deoxycytodine

Uracil Uridine Not usually found

Thymine Not usually found 2-deoxythymidine

Nucleotides are nucleosides + phosphate 71

 Nucleoside
Analogs as Drugs

72
Nucleotides

73
 Chemical Structure of DNA and RNA

Figure 4.1

The C is
named 1’-5’
4’ 1’
2’

Nucleotide
Nucleoside

RNA DNA
74
DNA Stabilization– Complementary
Base Pairing

75
DNA Stabilization--H-bonding between DNA base
pair stacks

76
 Advantages to Double Helix
• Stability---protects bases from
attack by H2O soluble compounds
and H2O itself.

• Provides easy mechanism for

replication

77
 Physical Structure (cont’d)
• Chains are anti-parallel (i.e in opposite
directions)
• Diameter and periodicity are consistent
– 2.0 nm
– 10 bases/ turn
– 3.4 nm/ turn
• Width consistent because of
pyrimidine/purine pairing

78
Physical Structure (cont’d)

79
 Consequences of GC Content

 A=T, G=C, but AT≠GC

 Generally GC~50%, but extremely
variable

• GC slightly dense

• Higher number of base pairs=more stable

DNA, i.e. the strands don’t separate as
easily.

80
 Denaturation of DNA
• Denaturation by heating.
• How observed?
– A260
– For dsDNA,
A260=1.0 for 50 µg/ml
– For ssDNA and RNA
A260=1.0 for 38 µg/ml

The temperature at which – Hyperchromic shift

½ the DNA sample is
denatured is called the
melting temperature (Tm)

81
 RNA
• Types
– mRNA
– tRNA
– rRNA

• RNA world
– snRNA
– siRNA
– Ribozymes

82
 Structure of ATP
 Three phosphate
groups-(two with
high energy bonds

 Last phosphate
group (PO4)
contains the MOST
energy

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THANK YOU