Basic BiomedicalScience

International ClassProgram
Faculty of Medicine University ofIndonesia

Lecture 2
Organic: Carbohydrate, Protein, Lipid
Ade Arsianti, Department of Medical Chemisty
Faculty of Medicine University of Indonesia-2018

OVERVIEW
Carbohydrate, protein, and lipid are biomolecules produced by living organism. Carbohydrates,
which include the sugars and polysaccharides, have many important functions in biological
systems, such as serving as precursors for building many polymers, storing short-term energy,
and providing structural building materials. Proteins are composed of long chains of amino
acids joined together via peptide bonds. Proteins play a fundamental varied roles in cells and
tissues. Lipids are the basic building blocks of biological membranes, as well as energy storage.
 O
1. polyhydroxy ketone or C O
aldehyd C H
-OH > 1 -OH > 1

2. a larger molecule which can be hydrolyzed to

give a polyhydroxy aldehyde or ketone.

Type of Carbohydrates : classifications basedon

number of sugar units in totalchain
Monosaccharides single sugar unit (glucose, fructose, etc)
Disaccharides two sugar unit (sucrose, lactose, maltose)
Oligosaccharides 3 to 10 sugarunits
Polysaccharides more than 10 units (amylum, glycogen)
2
•Functions of Carbohydrates
1. Energy source for plants andanimals
2. Source of carbon in metabolicprocesses
3. Storage form of energy
4. Structural elements of cells andtissues

Photosynthesis and Respiration

• Photosynthesis in plants
requires CO2, H2O, and
energy from the sun and
produces carbohydrates,
such as glucose [C6H12O6
=C(H2O)6]. “hydrate” of
carbon

• In respiration, glucose is
oxidized in living cells to
produce CO2, H2O, and
energy.
3
 CHIRAL CENTER / CHIRAL CARBON CH OH
Ketose and
Classified by : Aldose 2
C O

1. Configuration of chiral carbon farthest from HO C H

the
1.polyhydroxy
carbonyl group ketone C 1CHO
O 1CHO
H C OH
HO 2C H H 2C OH
KETOSE -OH
3 > 1 H3 C OH
H C OH HO C H
2. Aldose or ketose 4 4 CH OH
H C OH HO C H2
5CH OH 5 CHCHO
2 2OH
3. Number of carbons in chain H C OH
O
2. polyhydroxy aldehyde C H HO C H
ALDOSE D-Arabinose
-OH > 1
H C OH
L-Arabinose
H C OH
4
 Aldohexose 1CHO 1CHO
2
1CHO

2
H C OH HO C H H 2C OH
• Mannosa :prevent the adhesion
of bacteria to tissues of the HO C
3
H HO 3C H HO 3 C H
urinary tract and bladder. 4 4 4
H C OH H C OH HO C H
D-Glucose is: 5
• found in fruits, corn syrup, and honey. H 5C OH H C OH H 5C OH
• known as blood sugar in the body. 6 CH2OH 6 CH2OH 6 CH2OH
• the most abundant organiccompound
found innature
D-Glucose D-Manose D-Galactose

Aldopentose
• Xylose : wood sugar, found in the D-Ribose is:
embryo of most edible plants. • Not used as energy source, but a part of the back
bone of RNA (genetic material ).
• Arabinose is a component of biopolymers
hemicellulose and pectin, can be metabolized •
When the C-2 OH is removed, the sugar becomes
by microorganisms as a carbon source deoxyribose which is used in the backbone of DNA.

1 C HO 1 CHO 1 CHO 1 CHO 1 CHO

H 2C OH H 2
HC HO C H 2
H C OH HO C H 2 2

H 3C OH H 3C
OH H 3 C OH HO C H
3 3
HO C H
4 4C
H C OH H OH H 4 C OH H 4 C OH H 4C OH
5 CH 2 O H 5 C H2O H 5 C H2 O H 5 CH 2 O H 5 CH 2 O H
5
D-Ribose D-2-deoksiribose D-Arabinose D-Xylose D-Liksose
 OH H

Fischer projection Haworth projection

OH
••foifrthDe-ssuugbasrtsittuheenhtishtoestthneurmigbhetriendthcearbon(furthest fromOH
thFeischaerpornoyjel)citsiodnr,aiwtwniulpb.eFdoraLw-snudgoawrsn,intis drawn down
-H the Haworth projection (Down-Right Rule)
H O
+ 6CH2OH
1C cyclization
2 5C O
H C OH H H
H
HO 3C H 4C 1C
•for D-sugars, the OH OH H
4C OH
H OH O group at the anomeric OH C3 2C
5C position is drawn down for
H O H  and up for . For L- H OH
6 C H2O H sugars  is up and  is
down
D-Glucose  - D - Glucopyranose

Hemiacetal cyclic
( Haworth projection)

6
Chair conformation
 H OH H O HO H
C1 C1 C1
H C OH H C2 OH H C OH
HO C H HO C H
HO C3 H
H C OH O H C4 OH H C OH O
H C5 H C5 OH H C5
CH2OH C6H2OH CH2OH
D-glucose
OH lactol = OH
Anomeric cargbolyncosidic
OH
REDUCING SUGAR
-D-glucopyranose -D-glucopyranose

OH

Chair conformation H 7
Chair conformation
 MUTAROTATION
The change of specific rotatation that accompanies with the equilibrium of alpha
and beta anomer in aqueous solution.

OH O HO H
H H
C C C
H C OH H C OH H C OH
HO C H HO C H HO C H
H C OH O H C OH H C OH O
H C H C OH H C
CH2OH CH2OH CH2OH

[  ] + 52.50

crystallize below 980C crystallize above 980C

-D-Glucopyranose -D-Glucopyranose
8
Monosa 1 Monosa 2
C C 1. C- OH glycosidic vs C - OH alcohol
monosa 1 monosa 2
OH
O
H
C–O–C
 -1,4 glucosidic
6 CH2OH 6 CH2OH
5 O 5 O - H2O 6 CH2OH 6 CH2OH
1 1 5
4 OH Lactol 4 OH O 5 O
1 4 1
HO OH HO 4 OH
3 2 3 2 OH Lactol OH
O free
OH OH HO 3 2 3 2 OH lactol
-D-Glucopyranose -D-Glucopyranose OH OH
-D-Glucopyranose -D-Glucopyranose

4-o-( -D-Glucopyranosyl)- -D-Glucopyranose

Maltose
REDUCING SUGAR. WHY ? 9
 2. C- OH glycosidic vs C - OH glycosidic
monosa 1 monosa 2

C–O–C
-D-Glucopyranose
6 CH2OH -D-Glucopyranose
5 O 6 CH2OH
1 5
4 OH
Lactol
O -D-Glucopyranosyl- -D-fructofuranoside
HO 4 OH
1 or
OH
3 2
HO -D-Fructofuranosyl -  -D-Glucopyranosid
OH 3 2
- H2O OH
6
HOCH2 O H Lactol
O 6
O Sucrose/saccarose
5 2 HOCH2 O
HO Glucose + fructose sucrose
CH2 OH 5 2
4 3 1 HO
OH CH2 OH
4 3 1
-D-Fructofuranose OH
NON REDUCING SUDAR. WHY ?
-D-Fructofuranose 10
Lactose
•Also called milk sugar.
•Composed of galactose and
glucose linked by a -1,4-
glycosidic bond

Sucrose
> also known as tablet sugar
> commercially obtained from sugar cane or sugarbeet
>hydrolysis yield glucose and fructoseinvert
sugar(invert sugar)
Sugar cane
H2O,H+ D-glucose + D – fructose
Sucrose
Hydrolysis
( + 52,50) ( -92,40 )

+ 66,50 INVERT - 39 ,70

> used pharmaceutically to make
Sugar beet
syrups, troches 11
 monosaccharide condensation polimer
white solid
less water soluble
not sweet
non aldose / ketose

1. Homopolysaccharide
produces one kind of monosaccharide on
hydrolysis

2. Heteropolysaccharide
produces other substances on hydrolysis
 OH OH

1. Starch
O O OH O
O OH
OH
OH OH

The glycosidic bonds in starch O are a-1,4 linkages.

O OH
OH
OH O
It turns out that there are different O kinds of starch, one
OH
OH
OH

is amylose and another is amylopectin. Plants conver t the

OH OH
O O OH
OH O
glucose into  -1,4’ AMYLOSE
starch
OH
O
O
CH OH OH

OH OH
O1,6’ glucosidic
2
O AMYLOSE O O -
AMYLOPECTIN OH
O OH
OH
4 1 OH O
1
OH
OH
O
OH
O linkage
OH branch
OH
point
O O OH
O O O
OH O
OH n OH OH
OH
O OH

* unbranched (spiral) * branched

OH OH
O OH
6 CH 2 O
OH
OH OH OH OH O
OH OH O
*300 – 400 glucose * 3000 glucose
O O O O
O
OH OH OH
OH OH O OOH O
O H branch : (1,6)
O OH OH

glycosidic OH
 (1,4) O H glycosidic OH  (1,4).
O O O OH
OH O O H
OH O OH
*with I2 deep blue *O with I2 purplish red
n OH OHn O
O CH 2
OH OH
OH OH
O
O OH
OH

amylase breaks (1,4)OH.but not (1,6)

Amylopectin O O OH O OH
OH
O
O
OH 13
 2. Glycogen
Glucose polymer,similar to
amylopectin a-1,4 linkages and a-1,6
linkages, but even more highly
branched.
Energy storage in muscle tissue and
liver.

3. Cellulose
A linear polymer of approximately
2800 D-glucose units per molecule
joined by -1,4- glycosidic bonds.
Cellulose is one form of
carbohydrate that plants use as a
building material to provide
structural strength rather than
for storing glucose for future use
•Human cannot digest cellulose,
because we do not possess enzyne
cellulase which can break -1,4-
glycosidic bonds in cellulose. 14
 Chitin is another example of a structural carbohydrate.
Chitin is found in the exoskeletons of insects, spiders, and
Chit in, a st ruct ural polysaccharide
crustaceans. Chitin is also found in the cell walls of fungi.
Chitin is leathery in pure form but is hardened in most
uses via the deposition of calcium carbonate.

CH2OH

H O OH
H
OH H
OH H

H
NH

C O
CH3

Composed of units of N-
acetyl--D-glucosamine joined
by -1,4-glycos idic bonds
(b) Chitin forms the exoskeleton (c) Chitin is used to ma ke a
(a) The structure of the of arthropods. This cicada strong and flexible surgical
chitin mo nomer. is molting, shedding its old thread that decomp oses after
exoskeleton and emerging the wound or incision heals.
in adult form.

15
 •

Although more than 300 different amino acids have been described in nature, only 20 are
commonly found as constituents of mammalian proteins, which can be placed in the category of
either essential or non-essential. Essential amino acids are those that are "essential" in the diet.
In other words, we cannot create them through our own metabolism. Therefore, we need to
obtain them through foods containing them. Non-essential amino acids are those which can be
produced from other amino acids and substances in the diet and metabolism.
10 of Essential amino acids : arginine (Arg), histidine (His), isoleucine (Ile), leucine (Leu), lysine
(Lys), methionine (Met), phenylalanine (Phe), threonine (Thr), tryphtophan (Trp), valine (Val).

10 of Non-essential amino acids : alanine (Ala), asparagine (Asn), Aspartate (Asp), cysteine
(Cys), glutamat (Glu), glutamine (Gln), glycine (Gly), proline (Pro), serine (Ser), tyrosine (Tyr).

A. Amino acids with nonpolar side chains

C.Amino acids with acidic sidechains
D. Amino acids withbasic side chains

B. Amino acids with

uncharged polar sidechains
• The twenty amino acids commonly found in
proteins are joined together by peptide bonds
to form a polypeptidechain
• Such a chain is a component of a hierarchy The sequence of amino acids in a protein is called
for describing macromolecularstructure the primary structure of the protein.
• The peptide linkage is planar and rigid

The -helix, -sheet, and loops (coils) are examples of

secondary structures frequently encountered in proteins.
Hydrogen bonds maintain the secondary structure

A globular amino acid polymer folded, formed and stabilized

by hydrogen bonding, covalent (e.g. disulfide) bonding,
hydrophilic and hydrophobic forces.

Built from 2 or more of polypeptide subunits (monomeric).

Denaturation of proteins
Protein denaturation results in the
unfolding and disorganization of the
protein's secondary, tertiary and
quaternary structures, which are not
accompanied by hydrolysis of peptide
bonds. Denaturing agents include
heat, organic solvents, mechanical
mixing, strong acids or bases,
detergents, and ions of heavy metals
such aslead and mercury
 Five (5) types of lipids:
• Energy-storage lipids:
triacylglycerols
• Membrane lipids:
phospholipids
• Emulsification lipids: bile
• Messenger lipids:steroid
hormones
• Protective lipids:
biological waxes

Classification of Lipids

FATTY ACIDS: GLYCERIDES: NONGLYCERIDES: COMPLEX LIPID:

Saturated Neutral Sphingolipids Lipoproteins
Unsaturated Phosphoglycerides Steroid Glycolipids
Waxes
22
Fatty acids: a component of
many lipids Some fatty acids and their common names:
14:0 myristic acid; CH3(CH2)12-COOH
• Monocarboxylic acids. 16:0 palmitic acid; CH3(CH2)14-COOH

• Different types of fattyacids: 18:0 stearic acid; CH3(CH2)16-COOH

– Saturated fatty acid
18:1 cis9 oleic acid CH3(CH2)7CH=CH(CH2)7-COOH

– Unsaturated fatty acid

• Monounsaturated fatty acid: exp (20:1).
• Polyunsaturated fatty acids (PUFA): exp(20:3).
• Biosynthesized fatty acids are further classifiedas:
– Long-chain: contain 12-26 carbons
– Medium-chain: contain 6-10carbons
– Short-chain: contain 4-6carbons
Double bonds in fatty acids usually have the cis configuration.
Most naturally occurring fatty acids have an even number of carbonatoms.
23
18:2 cis9,12 linoleic acid
CH3(CH2)4CH=CHCH2CH=CH(CH2)7-COOH
is used to synthesize arachidonic acid, which regulates blood
pressure, clotting et

18:3 cis9,12,15 a-linonenic acid

CH3CH2CH=CHCH2CH=CHCH2CH=CH(CH2)7-COOH
is used to synthesize eicosapentaenoic acid (EPA) and docosahexanoic aci
(DHA) which are required for normal brain function and development (an
omega-3)

20:4 cis5,8,11,14 arachidonic acid

20:5 cis5,8,11,14,17 eicosapentaenoic acid(anomega-3 )
24
 O
H
O H C-OH -O-C-CH2C-R1
H
R2-CH2-C-OHHO- CH O
-O-C-CH
H
H C- OH 2C-R3
H
Diacylglycerol/ Monoacylglycerol/monoglyceride
diglyceride
Triacylglycerol = Triglyceride
glycerol
25
 Hydrogenated Fats
• Hydrogenation of
vegetable oils to
margarine or
shortening, not only
convert unsaturated
bond to saturated, but
also may converts
some of cis
unsaturated bonds to
trans configuration
• Diet high in trans fatty
acids risks heart
disease, cancer.
Oxidation: addition of oxygen
(derived from air), lead to oxidize
the double bonds present in a fatty
acid to produce low –molecular-mass
- COOH
and volatile compound, such as ( fatty acid)
carboxylic acid, and other carbonyl
compound (keton, aldehyd) through H2O
peroxide intermediate. This volatile - C = C - + O2 -C - C - - CHO
compounds are responsible for   - C=O
rancid odor and flavor in some food
products. Antioxidant is usually O - O
added to prevent lipid oxidation (Peroxide)
which lead to rancidity 26
• Glycerol esterified with 2 fatty
acids.
• Third position is phosphate
• Other end of phosphate can
combine with other molecules
to form variousderivatives
• Amphipathic –emulsifying PHOSPHATE
agents
• component of cell membrane

H
Lecithin (phosphatidyl
Phosphatidyl
choline), a common OH
food additive, is a inositol OH
H OH
phospholipid, OH H
Which embedded in H H
cell membranes.
H OH

27
Cell Membrane

28
The amino group of sphingosine can Sphingolipids
form an amide bond with carboxylate •Sphingosine instead of glycerol
group of a fatty acid, to yield a •Derivatization at ester C1
•Fatty acids added at amine
ceramide Ceramides usually include
•Different types areafound
polar head
in plasma
Sphingomyelins group, esterified
membranetoand
the terminal
myelin sheaths OH

are found of the sphingosine

abundantly in the CHC3H2OH O
myelin sheath that +
H2 HO2 
surrounds the H3C OH N C C O P O
H
nerve fibers OH H OH
CH 3 OH OH
H H
Sphingomyelin, a ceramide H
H2C C CH
with a phosphocholine or H OH
A cerebroside is a head
phosphethanolamine H2N CH
sphingolipid
group, (ceramide)
is a common with a
constituent
OH
monosaccharide such as
of plasma membranes O C CH
glucose or galactose as polar
Sphingomyelin
head group. Sphingolipids
R (CH2 )12
/ceramid egne
sphin 29
osi CH 3
Cholesterol: Precursor to Vitamin D
-important constituent of cell
membranes
-has a rigid ring system and a
short branched hydrocarbon
tail.
- Precursor to Bile Acids:
- Crusial role in lipid
digestion HO
- break up large lipid to
smaller one, make it amphipathic. hydrophobic
can be broken easily
by enzymes Precursor to steroid hormones that
regulate gene expression
Keeps the lipids in membrane
from aggregrating, eliminate of
excess cholesterol in intestinal
tract and artery.

An artery clogged by
A normal, open artery.
cholesterol pla q ue
30