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Basic Molecule in Cell
Basic Molecule in Cell
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
• 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
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.
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
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
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 )
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
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
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).
Classification of Lipids
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
An artery clogged by
A normal, open artery.
cholesterol pla q ue
30